256:, β4-galactosyl transferase (GalTI),β3-galactosyl transferase (GalT-II), and β3-GlcA transferase (GlcAT-I) transfer the four monosaccharides, begins synthesis of the GAG modified protein. The first modification of the tetrasaccharide linker determines whether the HSGAGs or CSGAGs will be added. Addition of a GlcNAc promotes the addition of HSGAGs while addition of GalNAc to the tetrasaccharide linker promotes CSGAG development. GlcNAcT-I transfers GlcNAc to the tetrasaccahride linker, which is distinct from glycosyltransferase GlcNAcT-II, the enzyme that is utilized to build HSGAGs. EXTL2 and EXTL3, two genes in the EXT tumor suppressor family, have been shown to have GlcNAcT-I activity. Conversely, GalNAc is transferred to the linker by the enzyme GalNAcT to initiate synthesis of CSGAGs, an enzyme which may or may not have distinct activity compared to the GalNAc transferase activity of chondroitin synthase.
86:
551:, hyaluronic acid forms randomly kinked coils that entangle to form a hyaluronan network, slowing diffusion and forming a diffusion barrier that regulates transport of substances between cells. For example, hyaluronan helps partition plasma proteins between vascular and extravascular spaces, which affects solubility of macromolecules in the interstitium, changes chemical equilibria, and stabilizes the structure of collagen fibers.
2746:
385:
489:, in which GAGs levels such as KS are altered, loss of hydration within the corneal stroma is believed to be the cause of corneal haze, thus supporting the long-held hypothesis that corneal transparency is dependent on proper levels of keratan sulfate. Keratan sulfate GAGs are found in many other tissues besides the cornea, where they are known to regulate
36:
477:) through its receptor. CSGAGs are important in providing support and adhesiveness in bone, skin, and cartilage. Other biological functions for which CSGAGs are known to play critical functions in include inhibition of axonal growth and regeneration in CNS development, roles in brain development, neuritogenic activity, and pathogen infection.
585:. Stem cells are protected from the effects of growth factors by a shield of hyaluronan and minimally sulfated chondroitin sulfate. During progenitor division, the daughter cell moves outside of this pericellular shield where it can then be influenced by growth factors to differentiate even further.
295:
Chondroitin sulfate and dermatan sulfate, which comprise CSGAGs, are differentiated from each other by the presence of GlcA and IdoA epimers respectively. Similar to the production of HSGAGs, C-5 uronyl epimerase converts d-GlcA to l-IdoA to synthesize dermatan sulfate. Three sulfation events of the
472:
CSGAGs interact with heparin binding proteins, specifically dermatan sulfate interactions with fibroblast growth factor FGF-2 and FGF-7 have been implicated in cellular proliferation and wound repair while interactions with hepatic growth factor/scatter factor (HGF/SF) activate the HGF/SF signaling
426:
from 10 to 10 Da. Each HAS enzyme is capable of transglycosylation when supplied with UDP-GlcA and UDP-GlcNAc. HAS2 is responsible for very large hyaluronic acid polymers, while smaller sizes of HA are synthesized by HAS1 and HAS3. While each HAS isoform catalyzes the same biosynthetic reaction,
467:
A) at pH within granules (5.2–6.0), thus it is believed that heparin, which is highly negatively charged, functions to electrostatically retain and store histamine. In the clinic, heparin is administered as an anticoagulant and is also the first line choice for thromboembolic diseases. Heparan
484:
One of the main functions of the third class of GAGs, keratan sulfates, is the maintenance of tissue hydration. Keratan sulfates are in the bone, cartilage, and the cornea of the eye. Within the normal cornea, dermatan sulfate is fully hydrated whereas keratan sulfate is only partially hydrated
501:
in the endometrial uterine lining during menstrual cycles, and affect the motility of corneal endothelial cells. In summary, KS plays an anti-adhesive role, which suggests very important functions of KS in cell motility and attachment as well as other potential biological
468:
sulfate (HS) has numerous biological activities and functions, including cell adhesion, regulation of cell growth and proliferation, developmental processes, cell surface binding of lipoprotein lipase and other proteins, angiogenesis, viral invasion, and tumor metastasis.
259:
With regard to HSGAGs, a multimeric enzyme encoded by EXT1 and EXT2 of the EXT family of genes, transfers both GlcNAc and GlcA for HSGAG chain elongation. While elongating, the HSGAG is dynamically modified, first by N-deacetylase, N-sulfotransferase
581:, part of which is constructed from hyaluronan, in order to shield themselves from bacteria, red blood cells, or other matrix molecules. For example, in regard to stem cells, hyaluronan, along with chondroitin sulfate, helps to form the
348:-linked oligosaccharide extension with keratan sulfate. Keratan sulfate elongation begins at the nonreducing ends of three linkage oligosaccharides, which define the three classes of keratan sulfate. Keratan sulfate I (KSI) is
251:
HSGAG and CSGAG modified proteoglycans first begin with a consensus Ser-Gly/Ala-X-Gly motif in the core protein. Construction of a tetrasaccharide linker that consists of -GlcAβ1–3Galβ1–3Galβ1–4Xylβ1-O-(Ser)-, where
434:
values for UDP-GlcA and UDPGlcNAc. It is believed that through differences in enzyme activity and expression, the wide spectrum of biological functions mediated by HA can be regulated, such as its involvement with
368:(β4Gal-T1) while the enzymes responsible for β-3-Nacetylglucosamine have not been clearly identified. Finally, sulfation of the polymer occurs at the 6-position of both sugar residues. The enzyme KS-Gal6ST (
1457:
DeAngelis PL, Weigel PH (1994). "Immunochemical confirmation of the primary structure of streptococcal hyaluronan synthase and synthesis of high molecular weight product by the recombinant enzyme".
1126:
1109:
364:
mannose. Elongation of the keratan sulfate polymer occurs through the glycosyltransferase addition of Gal and GlcNAc. Galactose addition occurs primarily through the β-1,4-galactosyltransferase
264:), which is a bifunctional enzyme that cleaves the N-acetyl group from GlcNAc and subsequently sulfates the N-position. Next, C-5 uronyl epimerase coverts d-GlcA to l-IdoA followed by 2-
554:
Other functions include matrix interactions with hyaluronan binding proteins such as hyaluronectin, glial hyaluronan binding protein, brain enriched hyaluronan binding protein,
54:
1979:
1932:
1814:
1689:
Sugahara K, Mikami T, Uyama T, Mizuguchi S, Nomura K, Kitagawa H (2003). "Recent advances in the structural biology of chondroitin sulfate and dermatan sulfate".
1171:"Evolution of glycosaminoglycans and their glycosyltransferases: Implications for the extracellular matrices of animals and the capsules of pathogenic bacteria"
1492:
Itano N; Sawai T; Yoshida M; Lenas P; Yamada Y; Imagawa M; Shinomura T; Hamaguchi M; Yoshida Y; Ohnuki Y; Miyauchi S; Spicer AP; McDonald JA; Kimata K (1999).
332:
consists of a series of tandemly repeated hexapeptides with a consensus sequence of E(E/L)PFPS. Additionally, for three other keratan sulfated proteoglycans,
2782:
537:
of hyaluronic acid makes it ideal for lubricating joints and surfaces that move along each other, such as cartilage. A solution of hyaluronic acid under low
328:
types, are driven towards biosynthesis through particular protein sequence motifs. For example, in the cornea and cartilage, the keratan sulfate domain of
1418:"In vitro synthesis of hyaluronan by a single protein derived from mouse HAS1 gene and characterization of amino acid residues essential for the activity"
545:, an enzyme produced by white blood cells, sperms cells, and some bacteria, breaks apart the hyaluronic acid, causing the solution to become more liquid.
242:(also known as hyaluronan), which is synthesized by integral membrane synthases, which immediately secrete the dynamically elongated disaccharide chain.
1907:
Gallagher, J.T., Lyon, M. (2000). "Molecular structure of
Heparan Sulfate and interactions with growth factors and morphogens". In Iozzo, M, V. (ed.).
1381:
Yamamoto Y, Takahashi I, Ogata N, Nakazawa K (2001). "Purification and characterization of N-acetylglucosaminyl sulfotransferase from chick corneas".
873:
Highly similar in structure to heparin, however heparan sulfate's disaccharide units are organised into distinct sulfated and non-sulfated domains.
2010:
1960:
1916:
1790:
571:
289:
273:
1131:
1114:
422:. HA, a linear polysaccharide, is composed of repeating disaccharide units of →4)GlcAβ(1→3)GlcNAcβ(1→ and has a very high molecular mass,
533:
of other connective tissues. Hyaluronic acid binds cells together, lubricates joints, and helps maintain the shape of the eyeballs. The
182:. This is because GAG synthesis is not template driven, as are proteins or nucleic acids, but constantly altered by processing enzymes.
1153:
72:
2775:
1952:
2884:
1976:
1227:
563:
352:-linked via a high mannose type precursor oligosaccharide. Keratan sulfate II (KSII) and keratan sulfate III (KSIII) are
594:
Members of the glycosaminoglycan family vary in the type of hexosamine, hexose or hexuronic acid unit they contain (e.g.
98:
485:
suggesting that keratan sulfate may behave as a dynamically controlled buffer for hydration. In disease states such as
2905:
2768:
2003:
211:
1144:
Esko, Jeffrey D; Kimata, Koji; Lindahl, Ulf (2009). "Chapter 16: Proteoglycans and
Sulfated Glycosaminoglycans".
574:), which has been implicated in developmental processes, tumor metastasis, and pathological reparative processes.
486:
2070:
1970:
2563:
2749:
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1996:
344:), the consensus sequence NX(T/S) along with protein secondary structure was determined to be involved in
233:
215:
2551:
997:
163:
85:
2690:
1584:
2835:
1831:
Laurent TC, Laurent UB, Fraser JR (1996). "The structure and function of hyaluronan: An overview".
1040:
659:
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372:) transfers sulfate groups to galactose while N-acetylglucosaminyl-6-sulfotransferase (GlcNAc6ST) (
219:
195:
94:
2814:
1926:
1808:
1208:
1093: – Viscous, carbohydrate rich layer at the outermost periphery of a cell. Pericellular coat.
1078:
312:
GalNAc sulfotransferases (C4ST-1, C4ST-2, C4ST-3, and D4ST-1) and three isoforms of the GalNAc 6-
253:
167:
316:
sulfotransferases (C6ST, C6ST-2, and GalNAc4S-6ST) are responsible for the sulfation of GalNAc.
427:
each HAS isoform is independently active. HAS isoforms have also been shown to have differing
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Kusche-Gullberg M, Kjellén L (2003). "Sulfotransferases in glycosaminoglycan biosynthesis".
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unit. GAGs are found in vertebrates, invertebrates and bacteria. Because GAGs are highly
149:
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Fibroblasts, mesothelial cells, and certain types of stem cells surround themselves in a
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in which abnormal accumulations of glycosaminoglycans occur due to enzyme deficiencies.
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1494:"Three isoforms of mammalian hyaluronan synthases have distinct enzymatic properties"
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566:. Cell surface interactions involving hyaluronan are its well-known coupling with
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223:
207:
185:
GAGs are classified into four groups, based on their core disaccharide structures:
133:
511:
Dermatan sulfates function in the skin, tendons, blood vessels, and heart valves.
410:(HA), is not sulfated and is synthesized by three transmembrane synthase proteins
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2727:
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1081: – Class of molecules found in the outer membrane of gram-negative bacteria
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17:
1884:
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1730:
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Proceedings of the
National Academy of Sciences of the United States of America
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Glycosaminoglycans vary greatly in molecular mass, disaccharide structure, and
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2503:
2445:
2440:
2313:
2266:
1702:
1536:
Rabenstein DL. (2002). "Heparin and heparan sulfate: structure and function".
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1255:"Glycomics Approach to Structure-Function Relationships of Glycosaminoglycans"
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2348:
2333:
2318:
2234:
2229:
2049:
2044:
1988:
329:
145:
136:
units (i.e. two-sugar units). The repeating two-sugar unit consists of a
1844:
1470:
160:
and attract water; the body uses them as lubricants or shock absorbers.
2868:
2720:
2700:
2668:
2643:
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790:
494:
423:
384:
333:
189:
1571:
Jin L, Abrahams JP, Skinner R, Petitou M, Pike RN, Carrell RW (1997).
324:
Unlike HSGAGs and CSGAGs, the third class of GAGs, those belonging to
2710:
2705:
2695:
2672:
2649:
2617:
2404:
2399:
2343:
2306:
2291:
2271:
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2219:
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2209:
2122:
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2034:
1549:
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782:
365:
455:
Endogenous heparin is localized and stored in secretory granules of
2296:
2099:
1632:
Heparin: Chemical and
Biological Properties, Clinical Applications
570:, which may be related to tumor progression, and also with RHAMM (
559:
474:
383:
376:) transfers sulfate groups to terminal GlcNAc in keratan sulfate.
373:
369:
357:
261:
84:
1253:
Sasisekharan, Ram; Raman, Rahul; Prabhakar, Vikas (August 2006).
828:
Highest negative charge density of any known biological molecule
567:
541:
has a much higher viscosity than while under high shear stress.
419:
415:
411:
2764:
1992:
1650:"Dermatan sulfate: new functions from an old glycosaminoglycan"
29:
1977:
MRI evaluation of glycosaminoglycan loss (dGEMRIC evaluation)
1909:
Proteoglycans: structure, biology and molecular interactions
734:
Distinguished from chondroitin sulfate by the presence of
1573:"The anticoagulant activation of antithrombin by heparin"
1327:
1325:
89:
The repeating disaccharide unit (GlcUA(1β→3)GalNAc(1β→4))
1868:"Keratan sulfate: structure, biosynthesis, and function"
1731:"Keratan sulfate: structure, biosynthesis, and function"
202:(CSGAGs) which along with HSGAGs are synthesized in the
50:
738:, although some hexuronic acid monosaccharides may be
1087: – External bodily secretion produced by snails
648:
Linkage geometry between predominant monomeric units
463:
that is present within the granules is protonated (H
2877:
2861:
2823:
2802:
2578:
2535:
2517:
2489:
2431:
2424:
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2364:
2257:
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2098:
2089:
2058:
2027:
45:
may be too technical for most readers to understand
1785:. Derrickson, Bryan (14th ed.). Danvers, MA.
1778:
1075: – Protein with oligosaccharide modifications
356:-linked, with KSII linkages identical to that of
308:sulfation of uronic acid. Four isoforms of the 4-
152:, where, in place of the uronic sugar there is a
1911:. New York: Marcel Dekker Inc. pp. 27–59.
1724:
1722:
1720:
1416:Yoshida M, Itano N, Yamada Y, Kimata K (2000).
1248:
1246:
1244:
908:The only GAG that is exclusively non-sulfated
284:positions of GlcNAc moities are sulfated by 6-
2776:
2004:
1643:
1641:
1531:
1529:
236:or O-linked glycosylation of the proteoglycan
8:
1931:: CS1 maint: multiple names: authors list (
1228:"Glycosaminoglycan Sulfation and Signaling"
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2428:
2095:
2011:
1997:
1989:
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1824:
1813:: CS1 maint: location missing publisher (
1969:at the U.S. National Library of Medicine
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1357:
1270:
1186:
1029:-D-N-acetylgalactosamine-4-O, 6-O-sulfate
73:Learn how and when to remove this message
57:, without removing the technical details.
626:
360:core structure, and KSIII linked to a 2-
268:sulfation of the uronic acid sugar by 2-
214:, are post-translationally modified via
1383:Archives of Biochemistry and Biophysics
1259:Annual Review of Biomedical Engineering
1148:. Cold Spring Harbor Laboratory Press.
1102:
232:which may modify core proteins through
1924:
1806:
1781:Principles of anatomy & physiology
1272:10.1146/annurev.bioeng.8.061505.095745
617:They also vary in the geometry of the
97:. For polysaccharide nomenclature see
27:Polysaccharides found in animal tissue
1961:Indiana University School of Medicine
1772:
1770:
1768:
1766:
1691:Current Opinion in Structural Biology
1296:Current Opinion in Structural Biology
572:Hyaluronan-mediated motility receptor
292:) and 3-O (3-OST) sulfotransferases.
55:make it understandable to non-experts
7:
1019:-D-N-acetylgalactosamine-6-O-sulfate
1009:-D-N-acetylgalactosamine-4-O-sulfate
290:Heparan sulfate 6-O-sulfotransferase
274:Heparan sulfate 2-O-sulfotransferase
1422:The Journal of Biological Chemistry
1630:Rodén, L. (1989). Lane, DA (ed.).
25:
1777:Tortora, Gerard J. (2013-12-31).
1169:DeAngelis, Paul L. (2002-11-01).
1062:-D-N-sulfoglucosamine-6-O-sulfate
2745:
2744:
1648:Trowbridge JM, Gallo RL (2002).
34:
1498:Journal of Biological Chemistry
781:Keratan sulfate type II may be
2885:Polysulfated glycosaminoglycan
1334:"Keratan sulfate biosynthesis"
638:hexose (for keratan)
1:
564:inter-alpha-trypsin inhibitor
1634:. CRC Press, Inc. p. 1.
1132:Dorland's Medical Dictionary
1115:Dorland's Medical Dictionary
144:, except in the case of the
1963:Accessed December 31, 2006.
1833:Immunology and Cell Biology
493:adhesion, form barriers to
212:rough endoplasmic reticulum
2922:
1146:Essentials of Glycobiology
876:
831:
788:
745:
692:
657:
624:Examples of GAGs include:
304:sulfation of GalNAc and 2-
113:may have different values.
2803:Unsulfated, extracellular
2740:
1729:Funderburgh, JL. (2000).
1703:10.1016/j.sbi.2003.09.011
1308:10.1016/j.sbi.2003.08.002
487:macular corneal dystrophy
406:The fourth class of GAG,
192:/heparan sulfate (HSGAGs)
2071:Cyclohexane conformation
1971:Medical Subject Headings
1885:10.1093/glycob/10.10.951
1866:Funderburgh JL. (2000).
1748:10.1093/glycob/10.10.951
1598:10.1073/pnas.94.26.14683
1511:10.1074/jbc.274.35.25085
1332:Funderburgh JL. (2002).
660:Chondroitin sulfate
521:is a major component of
132:consisting of repeating
2862:Sulfated, intracellular
2824:Sulfated, extracellular
2564:Isomaltooligosaccharide
1538:Natural Product Reports
1226:Caligur, Vicki (2008).
2558:Galactooligosaccharide
1395:10.1006/abbi.2001.2422
1350:10.1080/15216540214932
636:Hexuronic acid or
403:
296:CSGAG chains occur: 4-
234:N-linked glycosylation
216:O-linked glycosylation
114:
2552:Fructooligosaccharide
1667:10.1093/glycob/cwf066
1435:10.1074/jbc.275.1.497
1175:The Anatomical Record
1052:-D-N-sulfoglucosamine
998:N-acetylgalactosamine
387:
380:Hyaluronic acid class
320:Keratan sulfate types
164:Mucopolysaccharidoses
88:
1127:"mucopolysaccharide"
220:glycosyltransferases
2836:Chondroitin sulfate
1845:10.1038/icb.1996.32
1589:1997PNAS...9414683J
1471:10.1021/bi00197a001
1110:"glycosaminoglycan"
1041:N-acetylglucosamine
689:Most prevalent GAG
579:pericellular "coat"
499:embryo implantation
276:). Finally, the 6-
196:Chondroitin sulfate
168:metabolic disorders
126:mucopolysaccharides
95:chondroitin sulfate
2906:Glycosaminoglycans
2815:Sodium hyaluronate
2796:glycosaminoglycans
1982:2011-08-22 at the
1967:Glycosaminoglycans
1955:2023-02-08 at the
1950:Glycosaminoglycans
1079:Lipopolysaccharide
940:-D-glucuronic acid
619:glycosidic linkage
439:regulation in the
404:
272:sulfotransferase (
254:xylosyltransferase
148:glycosaminoglycan
118:Glycosaminoglycans
115:
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1918:978-0-8247-0334-9
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912:
911:
529:, as well as the
507:Dermatan sulfates
497:growth, regulate
128:are long, linear
83:
82:
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16:(Redirected from
2913:
2841:Dermatan sulfate
2785:
2778:
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2748:
2747:
2539:oligosaccharides
2519:Tetrasaccharides
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2144:Dihydroxyacetone
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1660:(9): 117R–125R.
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1583:(26): 14683–88.
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963:-L-iduronic acid
695:Dermatan sulfate
627:
531:ground substance
523:synovial tissues
481:Keratan sulfates
447:Pharmacodynamics
441:subgranular zone
437:neural stem cell
200:dermatan sulfate
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18:Glycoaminoglycan
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2853:Keratan sulfate
2848:Heparan sulfate
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2593:Oat beta-glucan
2580:Polysaccharides
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2410:Neuraminic acid
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1829:
1822:
1805:
1793:
1776:
1775:
1764:
1728:
1727:
1718:
1688:
1687:
1683:
1647:
1646:
1639:
1629:
1628:
1624:
1570:
1569:
1565:
1535:
1534:
1527:
1491:
1490:
1486:
1465:(31): 9033–39.
1456:
1455:
1451:
1415:
1414:
1410:
1380:
1379:
1375:
1331:
1330:
1323:
1293:
1292:
1288:
1252:
1251:
1242:
1232:
1230:
1225:
1224:
1220:
1168:
1167:
1163:
1156:
1143:
1142:
1138:
1125:
1121:
1108:
1104:
1100:
1069:
929:glucuronic acid
917:
850:
848:
846:
841:
839:
834:Heparan sulfate
805:
803:
801:
796:
758:
753:
748:Keratan sulfate
740:glucuronic acid
711:
709:
707:
702:
700:
674:
672:
670:
665:
653:Unique features
637:
596:glucuronic acid
592:
583:stem cell niche
535:viscoelasticity
519:Hyaluronic acid
515:Hyaluronic acid
466:
449:
433:
408:hyaluronic acid
402:
382:
340:, and mimecan (
326:keratan sulfate
322:
249:
247:HSGAG and CSGAG
240:Hyaluronic acid
230:Keratan sulfate
222:, thus forming
204:Golgi apparatus
176:
166:are a group of
158:polar molecules
130:polysaccharides
112:
108:
104:
92:
79:
68:
62:
59:
51:help improve it
48:
39:
35:
28:
23:
22:
15:
12:
11:
5:
2919:
2917:
2909:
2908:
2898:
2897:
2891:
2890:
2888:
2887:
2881:
2879:
2875:
2874:
2872:
2871:
2865:
2863:
2859:
2858:
2856:
2855:
2850:
2845:
2844:
2843:
2838:
2827:
2825:
2821:
2820:
2818:
2817:
2812:
2806:
2804:
2800:
2799:
2790:
2788:
2787:
2780:
2773:
2765:
2756:
2755:
2753:
2752:
2741:
2738:
2737:
2734:
2733:
2731:
2730:
2725:
2724:
2723:
2718:
2708:
2703:
2698:
2693:
2691:Levan beta 2→6
2688:
2683:
2682:
2681:
2665:
2654:
2653:
2652:
2636:
2627:
2622:
2621:
2620:
2615:
2610:
2605:
2600:
2595:
2584:
2582:
2576:
2575:
2573:
2572:
2567:
2561:
2555:
2549:
2543:
2541:
2533:
2532:
2530:
2529:
2523:
2521:
2515:
2514:
2512:
2511:
2506:
2501:
2495:
2493:
2491:Trisaccharides
2487:
2486:
2484:
2483:
2478:
2473:
2468:
2463:
2458:
2453:
2448:
2443:
2437:
2435:
2426:
2422:
2421:
2418:
2417:
2415:
2414:
2413:
2412:
2402:
2396:
2394:
2390:
2389:
2387:
2386:
2385:
2384:
2379:
2377:Mannoheptulose
2370:
2368:
2362:
2361:
2359:
2358:
2357:
2356:
2351:
2346:
2338:
2337:
2336:
2331:
2326:
2321:
2311:
2310:
2309:
2304:
2299:
2294:
2289:
2284:
2279:
2274:
2263:
2261:
2255:
2254:
2252:
2251:
2250:
2249:
2239:
2238:
2237:
2232:
2224:
2223:
2222:
2217:
2212:
2207:
2198:
2196:
2190:
2189:
2187:
2186:
2185:
2184:
2176:
2175:
2174:
2169:
2160:
2158:
2152:
2151:
2149:
2148:
2147:
2146:
2138:
2137:
2136:
2134:Glyceraldehyde
2127:
2125:
2119:
2118:
2116:
2115:
2114:
2113:
2111:Glycolaldehyde
2104:
2102:
2093:
2087:
2086:
2084:
2083:
2078:
2073:
2068:
2062:
2060:
2056:
2055:
2053:
2052:
2047:
2042:
2037:
2031:
2029:
2025:
2024:
2018:
2016:
2015:
2008:
2001:
1993:
1987:
1986:
1974:
1964:
1944:
1943:External links
1941:
1939:
1938:
1917:
1899:
1878:(10): 951–58.
1858:
1820:
1791:
1762:
1741:(10): 951–58.
1716:
1681:
1637:
1622:
1563:
1525:
1484:
1449:
1428:(1): 497–506.
1408:
1373:
1321:
1286:
1265:(1): 181–231.
1240:
1218:
1181:(3): 317–326.
1161:
1155:978-0879695590
1154:
1136:
1119:
1101:
1099:
1096:
1095:
1094:
1088:
1082:
1076:
1068:
1065:
1064:
1063:
1053:
1043:
1030:
1020:
1010:
1000:
987:
977:
964:
954:
941:
931:
916:
913:
910:
909:
906:
887:
884:
881:
875:
874:
871:
852:
843:
836:
830:
829:
826:
807:
798:
793:
787:
786:
779:
760:
755:
750:
744:
743:
732:
713:
704:
697:
691:
690:
687:
676:
667:
662:
656:
655:
650:
645:
640:
633:
591:
590:Classification
588:
587:
586:
575:
552:
546:
516:
504:
503:
482:
470:
469:
464:
453:
448:
445:
443:of the brain.
431:
400:
381:
378:
321:
318:
248:
245:
244:
243:
237:
227:
210:, made in the
193:
175:
172:
110:
106:
102:
90:
81:
80:
42:
40:
33:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2918:
2907:
2904:
2903:
2901:
2886:
2883:
2882:
2880:
2876:
2870:
2867:
2866:
2864:
2860:
2854:
2851:
2849:
2846:
2842:
2839:
2837:
2834:
2833:
2832:
2829:
2828:
2826:
2822:
2816:
2813:
2811:
2808:
2807:
2805:
2801:
2797:
2793:
2786:
2781:
2779:
2774:
2772:
2767:
2766:
2763:
2751:
2743:
2742:
2739:
2729:
2726:
2722:
2719:
2717:
2714:
2713:
2712:
2709:
2707:
2704:
2702:
2699:
2697:
2694:
2692:
2689:
2687:
2686:Hemicellulose
2684:
2680:
2677:
2676:
2675:
2674:
2670:
2666:
2664:
2663:
2659:
2655:
2651:
2648:
2647:
2646:
2645:
2641:
2637:
2635:
2631:
2628:
2626:
2623:
2619:
2616:
2614:
2611:
2609:
2606:
2604:
2601:
2599:
2596:
2594:
2591:
2590:
2589:
2586:
2585:
2583:
2581:
2577:
2571:
2568:
2565:
2562:
2559:
2556:
2553:
2550:
2548:
2545:
2544:
2542:
2540:
2534:
2528:
2525:
2524:
2522:
2520:
2516:
2510:
2507:
2505:
2502:
2500:
2497:
2496:
2494:
2492:
2488:
2482:
2479:
2477:
2474:
2472:
2469:
2467:
2464:
2462:
2459:
2457:
2454:
2452:
2449:
2447:
2444:
2442:
2439:
2438:
2436:
2434:
2433:Disaccharides
2430:
2427:
2423:
2411:
2408:
2407:
2406:
2403:
2401:
2398:
2397:
2395:
2391:
2383:
2382:Sedoheptulose
2380:
2378:
2375:
2374:
2373:Ketoheptoses
2372:
2371:
2369:
2367:
2363:
2355:
2352:
2350:
2347:
2345:
2342:
2341:
2340:Deoxy sugars
2339:
2335:
2332:
2330:
2327:
2325:
2322:
2320:
2317:
2316:
2315:
2312:
2308:
2305:
2303:
2300:
2298:
2295:
2293:
2290:
2288:
2285:
2283:
2280:
2278:
2275:
2273:
2270:
2269:
2268:
2265:
2264:
2262:
2260:
2256:
2248:
2245:
2244:
2243:
2240:
2236:
2233:
2231:
2228:
2227:
2226:Ketopentoses
2225:
2221:
2218:
2216:
2213:
2211:
2208:
2206:
2203:
2202:
2201:Aldopentoses
2200:
2199:
2197:
2195:
2191:
2183:
2180:
2179:
2177:
2173:
2170:
2168:
2165:
2164:
2163:Aldotetroses
2162:
2161:
2159:
2157:
2153:
2145:
2142:
2141:
2139:
2135:
2132:
2131:
2129:
2128:
2126:
2124:
2120:
2112:
2109:
2108:
2106:
2105:
2103:
2101:
2097:
2094:
2092:
2088:
2082:
2079:
2077:
2074:
2072:
2069:
2067:
2064:
2063:
2061:
2057:
2051:
2048:
2046:
2043:
2041:
2038:
2036:
2033:
2032:
2030:
2026:
2022:
2021:carbohydrates
2014:
2009:
2007:
2002:
2000:
1995:
1994:
1991:
1985:
1981:
1978:
1975:
1972:
1968:
1965:
1962:
1958:
1954:
1951:
1947:
1946:
1942:
1934:
1928:
1920:
1914:
1910:
1903:
1900:
1895:
1891:
1886:
1881:
1877:
1873:
1869:
1862:
1859:
1854:
1850:
1846:
1842:
1838:
1834:
1827:
1825:
1821:
1816:
1810:
1802:
1798:
1794:
1788:
1783:
1782:
1773:
1771:
1769:
1767:
1763:
1758:
1754:
1749:
1744:
1740:
1736:
1732:
1725:
1723:
1721:
1717:
1712:
1708:
1704:
1700:
1697:(5): 612–20.
1696:
1692:
1685:
1682:
1677:
1673:
1668:
1663:
1659:
1655:
1651:
1644:
1642:
1638:
1633:
1626:
1623:
1618:
1614:
1609:
1604:
1599:
1594:
1590:
1586:
1582:
1578:
1574:
1567:
1564:
1559:
1555:
1551:
1547:
1544:(3): 312–31.
1543:
1539:
1532:
1530:
1526:
1521:
1517:
1512:
1507:
1503:
1499:
1495:
1488:
1485:
1480:
1476:
1472:
1468:
1464:
1460:
1453:
1450:
1445:
1441:
1436:
1431:
1427:
1423:
1419:
1412:
1409:
1404:
1400:
1396:
1392:
1388:
1384:
1377:
1374:
1369:
1365:
1360:
1355:
1351:
1347:
1344:(4): 187–94.
1343:
1339:
1335:
1328:
1326:
1322:
1317:
1313:
1309:
1305:
1302:(5): 605–11.
1301:
1297:
1290:
1287:
1282:
1278:
1273:
1268:
1264:
1260:
1256:
1249:
1247:
1245:
1241:
1229:
1222:
1219:
1214:
1210:
1206:
1202:
1198:
1194:
1189:
1184:
1180:
1176:
1172:
1165:
1162:
1157:
1151:
1147:
1140:
1137:
1134:
1133:
1128:
1123:
1120:
1117:
1116:
1111:
1106:
1103:
1097:
1092:
1089:
1086:
1083:
1080:
1077:
1074:
1071:
1070:
1066:
1061:
1057:
1054:
1051:
1047:
1044:
1042:
1038:
1034:
1031:
1028:
1024:
1023:GalNAc(4S,6S)
1021:
1018:
1014:
1011:
1008:
1004:
1001:
999:
995:
991:
988:
985:
981:
978:
976:
972:
968:
965:
962:
958:
955:
953:
952:iduronic acid
949:
945:
942:
939:
935:
932:
930:
926:
922:
919:
918:
915:Abbreviations
914:
907:
905:
903:
898:
896:
891:
888:
885:
882:
880:
877:
872:
870:
868:
863:
861:
856:
853:
849:GlcNAc(6S) or
844:
837:
835:
832:
827:
825:
823:
818:
816:
811:
808:
804:GlcNAc(6S) or
799:
794:
792:
789:
784:
780:
778:
776:
771:
769:
764:
761:
756:
751:
749:
746:
741:
737:
736:iduronic acid
733:
731:
729:
724:
720:
719:
714:
712:GalNAc(4S,6S)
710:GalNAc(6S) or
708:GalNAc(4S) or
705:
698:
696:
693:
688:
685:
681:
677:
675:GalNAc(4S,6S)
673:GalNAc(6S) or
671:GalNAc(4S) or
668:
663:
661:
658:
654:
651:
649:
646:
644:
641:
639:
634:
632:
629:
628:
625:
622:
620:
615:
613:
609:
608:galactosamine
605:
601:
600:iduronic acid
597:
589:
584:
580:
576:
573:
569:
565:
561:
557:
553:
550:
547:
544:
543:Hyaluronidase
540:
536:
532:
528:
524:
520:
517:
514:
513:
512:
509:
508:
500:
496:
492:
488:
483:
480:
479:
478:
476:
462:
458:
454:
451:
450:
446:
444:
442:
438:
430:
425:
421:
417:
413:
409:
398:
394:
390:
386:
379:
377:
375:
371:
367:
363:
359:
355:
351:
347:
343:
339:
335:
331:
327:
319:
317:
315:
311:
307:
303:
299:
293:
291:
287:
283:
279:
275:
271:
267:
263:
257:
255:
246:
241:
238:
235:
231:
228:
225:
224:proteoglycans
221:
217:
213:
209:
208:protein cores
205:
201:
197:
194:
191:
188:
187:
186:
183:
181:
173:
171:
169:
165:
161:
159:
155:
151:
147:
143:
139:
135:
131:
127:
123:
119:
100:
96:
87:
77:
74:
66:
56:
52:
46:
43:This article
41:
32:
31:
19:
2795:
2667:
2656:
2638:
2570:Maltodextrin
2451:Isomaltulose
2242:Deoxy sugars
2178:Ketotetrose
2081:Mutarotation
1908:
1902:
1875:
1872:Glycobiology
1871:
1861:
1836:
1832:
1780:
1738:
1735:Glycobiology
1734:
1694:
1690:
1684:
1657:
1654:Glycobiology
1653:
1631:
1625:
1580:
1576:
1566:
1541:
1537:
1501:
1497:
1487:
1462:
1459:Biochemistry
1458:
1452:
1425:
1421:
1411:
1389:(1): 87–92.
1386:
1382:
1376:
1341:
1337:
1299:
1295:
1289:
1262:
1258:
1231:. Retrieved
1221:
1178:
1174:
1164:
1145:
1139:
1130:
1122:
1113:
1105:
1073:Glycoprotein
1059:
1055:
1049:
1045:
1036:
1032:
1026:
1022:
1016:
1012:
1006:
1002:
993:
989:
986:-D-galactose
983:
982:= 6-O-sulfo-
979:
970:
966:
960:
959:= 2-O-sulfo-
956:
947:
943:
937:
936:= 2-O-sulfo-
933:
924:
920:
901:
900:
894:
893:
889:
866:
865:
859:
858:
854:
821:
820:
814:
813:
809:
774:
773:
767:
766:
762:
727:
726:
722:
717:
716:
683:
679:
652:
647:
642:
635:
630:
623:
616:
593:
548:
539:shear stress
510:
506:
505:
471:
428:
405:
396:
392:
361:
353:
349:
345:
323:
313:
309:
305:
301:
297:
294:
285:
281:
277:
269:
265:
258:
250:
184:
177:
162:
138:uronic sugar
134:disaccharide
125:
121:
117:
116:
69:
60:
44:
2831:Chondroitin
2728:Xanthan gum
2716:Amylopectin
2588:Beta-glucan
2499:Maltotriose
2314:Ketohexoses
2267:Aldohexoses
2247:Deoxyribose
2182:Erythrulose
2140:Ketotriose
2130:Aldotriose
1839:(2): A1-7.
1233:25 November
1085:Snail slime
783:fucosylated
682:(1→3)GalNAc
612:glucosamine
556:collagen VI
142:amino sugar
2810:Hyaluronan
2504:Melezitose
2446:Isomaltose
2441:Cellobiose
2107:Aldodiose
1338:IUBMB Life
1098:References
1091:Glycocalyx
1013:GalNAc(6S)
1003:GalNAc(4S)
879:Hyaluronan
772:GlcNAc(6S)
759:GlcNAc(6S)
643:Hexosamine
502:processes.
491:macrophage
457:mast cells
389:Hyaluronan
174:Production
2878:Synthetic
2658:Galactose
2613:Cellulose
2603:Sizofiran
2527:Stachyose
2509:Raffinose
2476:Trehalose
2461:Lactulose
2282:Galactose
2205:Arabinose
2167:Erythrose
2019:Types of
1927:cite book
1809:cite book
1801:871018672
1197:0003-276X
1056:GlcNS(6S)
975:galactose
957:IdoUA(2S)
934:GlcUA(2S)
851:GlcNS(6S)
845:GlcNAc or
842:IdoUA(2S)
819:GlcNS(6S)
812:IdoUA(2S)
806:GlcNS(6S)
800:GlcNAc or
797:IdoUA(2S)
757:GlcNAc or
706:GalNAc or
703:IdoUA(2S)
669:GalNAc or
666:GlcUA(2S)
604:galactose
473:pathway (
461:Histamine
395:1-3GlcNAc
338:keratocan
300:and/or 6-
180:sulfation
154:galactose
63:July 2015
2900:Category
2750:Category
2679:Glycogen
2662:Galactan
2640:Fructose
2625:Chitosan
2598:Lentinan
2547:Acarbose
2481:Turanose
2425:Multiple
2366:Heptoses
2354:Rhamnose
2349:Fuculose
2334:Tagatose
2319:Fructose
2235:Xylulose
2230:Ribulose
2194:Pentoses
2156:Tetroses
2059:Geometry
2050:Pyranose
2045:Furanose
1980:Archived
1953:Archived
1894:11030741
1757:11030741
1711:14568617
1676:12213784
1558:12137280
1520:10455188
1444:10617644
1403:11469798
1368:12512857
1316:14568616
1281:16834555
1213:38827411
1205:12382327
1067:See also
847:GlcNS or
840:IdoUA or
838:GlcUA or
802:GlcNS or
795:GlcUA or
701:IdoUA or
699:GlcUA or
664:GlcUA or
391:(-4GlcUA
330:aggrecan
206:, where
146:sulfated
2869:Heparin
2721:Amylose
2669:Glucose
2644:Fructan
2634:Dextran
2630:Dextrin
2608:Zymosan
2471:Sucrose
2466:Maltose
2456:Lactose
2405:Nonoses
2400:Octoses
2393:Above 7
2329:Sorbose
2324:Psicose
2302:Mannose
2287:Glucose
2277:Altrose
2259:Hexoses
2172:Threose
2123:Trioses
2028:General
1853:8724014
1617:9405673
1585:Bibcode
1479:8049203
1359:2874674
980:Gal(6S)
791:Heparin
765:Gal(6S)
754:Gal(6S)
549:In vivo
495:neurite
424:ranging
334:lumican
190:Heparin
150:keratan
140:and an
49:Please
2711:Starch
2706:Pectin
2701:Mannan
2696:Lignin
2673:Glucan
2650:Inulin
2618:Chitin
2344:Fucose
2307:Talose
2292:Gulose
2272:Allose
2220:Xylose
2215:Ribose
2210:Lyxose
2100:Dioses
2076:Epimer
2066:Anomer
2040:Ketose
2035:Aldose
1973:(MeSH)
1915:
1892:
1851:
1799:
1789:
1755:
1709:
1674:
1615:
1605:
1556:
1518:
1477:
1442:
1401:
1366:
1356:
1314:
1279:
1211:
1203:
1195:
1152:
1033:GlcNAc
990:GalNAc
899:GlcNAc
886:GlcNAc
864:GlcNAc
752:Gal or
725:GalNAc
562:, and
452:HSGAGs
418:, and
366:enzyme
280:and 3-
2566:(IMO)
2560:(GOS)
2554:(FOS)
2536:Other
2297:Idose
1608:25092
1209:S2CID
1046:GlcNS
944:IdoUA
921:GlcUA
892:GlcUA
883:GlcUA
857:GlcUA
718:IdoUA
686:(1→4)
678:GlcUA
560:TSG-6
527:fluid
475:c-Met
374:CHST2
370:CHST1
358:mucin
262:NDST1
124:) or
1933:link
1913:ISBN
1890:PMID
1849:PMID
1815:link
1797:OCLC
1787:ISBN
1753:PMID
1707:PMID
1672:PMID
1613:PMID
1554:PMID
1516:PMID
1475:PMID
1440:PMID
1399:PMID
1364:PMID
1312:PMID
1277:PMID
1235:2012
1201:PMID
1193:ISSN
1150:ISBN
723:1-3'
631:Name
568:CD44
525:and
420:HAS3
416:HAS2
412:HAS1
122:GAGs
99:here
1959:.
1880:doi
1841:doi
1743:doi
1699:doi
1662:doi
1603:PMC
1593:doi
1546:doi
1506:doi
1502:274
1467:doi
1430:doi
1426:275
1391:doi
1387:392
1354:PMC
1346:doi
1304:doi
1267:doi
1183:doi
1179:268
1129:at
1112:at
1039:-D-
996:-D-
973:-D-
967:Gal
950:-L-
927:-D-
904:1-4
897:1-3
869:1-4
862:1-4
824:1-4
817:1-4
777:1-3
770:1-4
730:1-4
614:).
459:.
399:1-)
342:OGN
218:by
109:, R
105:, R
101:. R
93:of
53:to
2902::
2794::
2671:/
2660:/
2642:/
2632:/
1929:}}
1925:{{
1888:.
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1874:.
1870:.
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1837:74
1835:.
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1500:.
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1473:.
1463:33
1461:.
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1340:.
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1310:.
1300:13
1298:.
1275:.
1261:.
1257:.
1243:^
1207:.
1199:.
1191:.
1177:.
1173:.
1058:=
1048:=
1035:=
1025:=
1015:=
1005:=
992:=
969:=
946:=
923:=
785:.
742:.
621:.
610:,
606:,
602:,
598:,
558:,
414:,
336:,
2784:e
2777:t
2770:v
2012:e
2005:t
1998:v
1935:)
1921:.
1896:.
1882::
1855:.
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1817:)
1803:.
1759:.
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1678:.
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1283:.
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1263:8
1237:.
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1185::
1158:.
1060:α
1050:α
1037:α
1027:β
1017:β
1007:β
994:β
984:β
971:β
961:α
948:α
938:β
925:β
902:β
895:β
890:-
867:α
860:β
855:-
822:α
815:α
810:-
775:β
768:β
763:-
728:β
721:β
715:'
684:β
680:β
465:2
432:m
429:K
401:n
397:β
393:β
362:O
354:O
350:N
346:N
314:O
310:O
306:O
302:O
298:O
288:(
286:O
282:O
278:O
270:O
266:O
260:(
226:.
198:/
120:(
111:3
107:2
103:1
91:n
76:)
70:(
65:)
61:(
47:.
20:)
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