291:
310:
1054:
1035:
524:
1217:
1275:
271:
882:
329:
345:
357:
1019:
31:
922:
953:
PDT is considered a noninvasive cancer treatment, involving the interaction between light of a determined frequency, a photo-sensitizer, and oxygen. This interaction produces the formation of a highly reactive oxygen species (ROS), usually singlet oxygen, as well as superoxide anion, free hydroxyl
309:
954:
radical, or hydrogen peroxide. These high reactive oxygen species react with susceptible cellular organic biomolecules such as; lipids, aromatic amino acids, and nucleic acid heterocyclic bases, to produce oxidative radicals that damage the cell, possibly inducing apoptosis or even necrosis.
195:
core. The periphery of the porphyrins, consisting of sp-hybridized carbons, generally display small deviations from planarity. "Ruffled" or saddle-shaped porphyrins is attributed to interactions of the system with its environment. Additionally, the metal is often not centered in the
161:, a rare chemical compound of exclusively theoretical interest. Substituted porphines are called porphyrins. With a total of 26 π-electrons, of which 18 π-electrons form a planar, continuous cycle, the porphyrin ring structure is often described as
290:
978:
Porphyrins have been investigated as possible anti-inflammatory agents and evaluated on their anti-cancer and anti-oxidant activity. Several porphyrin-peptide conjugates were found to have antiviral activity against HIV
394:
had its origins in the isolation of porphyrins from petroleum. This finding helped establish the biological origins of petroleum. Petroleum is sometimes "fingerprinted" by analysis of trace amounts of nickel and
2452:
Vogel E, Scholz P, Demuth R, Erben C, Bröring M, Schmickler H, et al. (October 1999). "Isoporphycene: The Fourth
Constitutional Isomer of Porphyrin with an N(4) Core-Occurrence of E/Z Isomerism".
2074:
Yella A, Lee HW, Tsao HN, Yi C, Chandiran AK, Nazeeruddin MK, et al. (November 2011). "Porphyrin-sensitized solar cells with cobalt (II/III)-based redox electrolyte exceed 12 percent efficiency".
1490:
Senge MO, MacGowan SA, O'Brien JM (December 2015). "Conformational control of cofactors in nature - the influence of protein-induced macrocycle distortion on the biological function of tetrapyrroles".
1360:"Catalytic activity of multi-wall carbon nanotube supported manganese (III) porphyrin: an efficient, selective and reusable catalyst for oxidation of alkenes and alkanes with urea–hydrogen peroxide"
322:
TPP)is another synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, TPP is highly symmetrical. Another difference is that its methyne centers are occupied by phenyl groups.
2125:
Alonso-Castro AJ, Zapata-Morales JR, Hernández-Munive A, Campos-Xolalpa N, Pérez-Gutiérrez S, Pérez-González C (May 2015). "Synthesis, antinociceptive and anti-inflammatory effects of porphyrins".
642:
505:. This molecule undergoes a number of further modifications. Intermediates are used in different species to form particular substances, but, in humans, the main end-product
1263:. The third porphyrin that is porphyrin-(2.1.1.0), was reported by Callot and Vogel-Sessler. Vogel and coworkers reported successful isolation of porphyrin-(3.0.1.0) or
169:
is that porphyrins typically absorb strongly in the visible region of the electromagnetic spectrum, i.e. they are deeply colored. The name "porphyrin" derives from
1053:
2425:
Vogel E, Guilard R (November 1993). "New
Porphycene Ligands: Octaethyl‐ and Etioporphycene (OEPc and EtioPc)—Tetra‐ and Pentacoordinated Zinc Complexes of OEPc".
2514:
Chmielewski PJ, Latos-Grażyński L, Rachlewicz K, Glowiak T (18 April 1994). "Tetra‐p‐tolylporphyrin with an
Inverted Pyrrole Ring: A Novel Isomer of Porphyrin".
1271:. The inversion of one of the pyrrolic subunits in the macrocyclic ring resulted in one of the nitrogen atoms facing outwards from the core of the macrocycle.
2355:
Nagamaiah J, Dutta A, Pati NN, Sahoo S, Soman R, Panda PK (March 2022). "3,6,13,16-Tetrapropylporphycene: Rational
Synthesis, Complexation, and Halogenation".
270:
1710:
Zhang B, Lash TD (September 2003). "Total synthesis of the porphyrin mineral abelsonite and related petroporphyrins with five-membered exocyclic rings".
1034:
2047:
475:
2581:
1859:
Giuntini F, Boyle R, Sibrian-Vazquez M, Vicente MG (2014). "Porphyrin conjugates for cancer therapy". In Kadish KM, Smith KM, Guilard R (eds.).
2465:
2269:
1040:
217:
714:
467:
721:
942:(PDT) since they strongly absorb light, which is then converted to heat in the illuminated areas. This technique has been applied in
328:
1694:
1552:
78:
1875:
1465:
3071:
904:, first reported in 1936, which is also the basis for more recent methods described by Adler and Longo. The general scheme is a
2549:
356:
1737:
Mason GM, Trudell LG, Branthaver JF (1989). "Review of the stratigraphic distribution and diagenetic history of abelsonite".
761:
754:
1399:
Ivanov AS, Boldyrev AI (August 2014). "Deciphering aromaticity in porphyrinoids via adaptive natural density partitioning".
344:
862:
685:
363:
678:
2574:
1331:
1018:
967:
909:
797:
303:
OEP) is a synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, OEP is highly symmetrical.
230:
usually has a charge of 2+ or 3+. A schematic equation for these syntheses is shown, where M = metal ion and L = a
3076:
1074:
Several heterocycles related to porphyrins are found in nature, almost always bound to metal ions. These include
790:
649:
387:
is possibly the only geoporphyrin mineral, as it is rare for porphyrins to occur in isolation and form crystals.
2010:
Lewtak JP, Gryko DT (October 2012). "Synthesis of π-extended porphyrins via intramolecular oxidative coupling".
555:
542:
482:
463:
143:
2795:
750:
523:
471:
2889:
2567:
1827:
Adler AD, Longo FR, Finarelli JD, Goldmacher J, Assour J, Korsakoff L (1967). "A simplified synthesis for
769:
3061:
2988:
2967:
2895:
1267:. The Japanese scientist Furuta and Polish scientist Latos-Grażyński almost simultaneously reported the
963:
905:
805:
103:
87:
2554:
2045:
Walter MG, Rudine AB, Wamser CC (2010). "Porphyrins and phthalocyanines in solar photovoltaic cells".
2885:
2875:
2693:
2599:
2083:
1746:
1638:
1581:
1371:
1248:
943:
939:
890:
729:
693:
606:
512:
The following scheme summarizes the biosynthesis of porphyrins, with references by EC number and the
502:
494:
391:
375:
A geoporphyrin, also known as a petroporphyrin, is a porphyrin of geologic origin. They can occur in
315:
2820:
2213:"Penetrating the Blood-Brain Barrier with New Peptide-Porphyrin Conjugates Having anti-HIV Activity"
1963:"Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics"
3081:
3066:
2881:
2836:
2810:
1120:
826:
621:
565:
424:
188:
2959:
1231:
was reported by
Emanual Vogel and coworkers in 1986. This isomer porphyrin-(2.0.2.0) is named as
3001:
2871:
2380:
2310:
2107:
901:
876:
296:
204:
plane. These nonplanar distortions are associated with altered chemical and physical properties.
131:
2648:
2211:
Mendonça DA, Bakker M, Cruz-Oliveira C, Neves V, Jiménez MA, Defaus S, et al. (June 2021).
200:
plane. For free porphyrins, the two pyrrole protons are mutually trans and project out of the N
2800:
2728:
2678:
2469:
2372:
2302:
2265:
2242:
2193:
2142:
2099:
2027:
1992:
1943:
1894:
1774:
1690:
1680:
1607:
1548:
1517:
1416:
1274:
841:
506:
439:
277:
166:
147:
3024:
857:
821:
785:
745:
709:
673:
637:
600:
3014:
2923:
2917:
2867:
2660:
2523:
2496:
2461:
2434:
2407:
2364:
2337:
2294:
2232:
2224:
2183:
2173:
2134:
2091:
2056:
2019:
1982:
1974:
1933:
1925:
1886:
1841:
1809:
1782:
1754:
1719:
1656:
1646:
1597:
1589:
1540:
1507:
1499:
1446:
1408:
1379:
1252:
1221:
1216:
1134:
95:
49:
2980:
2738:
2683:
2623:
1434:
1301:
1004:
657:
613:
486:
1129:
several versions of bacteriochlorophyll exist (sidechain; some use a usual chlorin ring)
2162:"Synthesis and bioactivity of oxovanadium(IV)tetra(4-methoxyphenyl)porphyrinsalicylates"
2087:
1750:
1642:
1585:
1375:
527:
Heme B biosynthesis pathway and its modulators. Major enzyme deficiences are also shown.
2913:
2757:
2733:
2237:
2212:
2188:
2161:
1987:
1962:
1938:
1913:
1602:
1569:
1338:
1244:
996:
894:
833:
416:
170:
151:
1961:
Singh S, Aggarwal A, Bhupathiraju NV, Arianna G, Tiwari K, Drain CM (September 2015).
1593:
509:
is combined with iron to form heme. Bile pigments are the breakdown products of heme.
3055:
3032:
2941:
2935:
2859:
2828:
2688:
2384:
2314:
2298:
1929:
1833:
1758:
1327:
1181:
1109:
852:
740:
704:
668:
632:
595:
498:
459:
2228:
2111:
995:
in environmental toxicology studies. While excess production of porphyrins indicate
816:
780:
2953:
2633:
2591:
2487:
Hiroyuki F (1994). ""N-Confused
Porphyrin": A New Isomer of Tetraphenylporphyrin".
1914:"A role for hydrogen peroxide in the pro-apoptotic effects of photodynamic therapy"
1890:
1544:
881:
584:
572:
435:
420:
208:-rings are more distinctly nonplanar, but they are more saturated than porphyrins.
1384:
1359:
1220:
Porphycene, first porphyrin isomer, synthesised from bipyrrole dialdehyde through
1723:
2931:
2628:
2466:
10.1002/(SICI)1521-3773(19991004)38:19<2919::AID-ANIE2919>3.0.CO;2-W
1978:
1317:
1307:
1205:
947:
490:
205:
162:
139:
123:
91:
2949:
2805:
2711:
2670:
2618:
2178:
2138:
2060:
1570:"Conservation of the conformation of the porphyrin macrocycle in hemoproteins"
1450:
550:
428:
408:
384:
115:
2720:
2613:
2368:
2095:
1326:
Corphins, the highly reduced porphyrin coordinated to nickel that binds the
1289:
1240:
992:
966:
and photonics. Synthetic porphyrin dyes have been incorporated in prototype
517:
380:
376:
24:
2527:
2473:
2438:
2376:
2341:
2306:
2246:
2197:
2146:
2103:
2031:
1996:
1947:
1898:
1772:
Rothemund P (1936). "A New
Porphyrin Synthesis. The Synthesis of Porphin".
1521:
1420:
1204:
is a porphyrin with a benzene ring fused to one of the pyrrole units. e.g.
1800:
Rothemund P (1935). "Formation of
Porphyrins from Pyrrole and Aldehydes".
1611:
1255:
to took up the challenge of preparing porphyrin-(2.1.0.1) and named it as
489:(PBG), which contains a pyrrole ring. Four PBGs are then combined through
3009:
2638:
2559:
1686:
1140:
913:
451:
412:
158:
34:
20:
2500:
1845:
1813:
1786:
2905:
2555:
Porphynet – an informative site about porphyrins and related structures
2023:
1876:"Photodynamic therapy for neovascular age-related macular degeneration"
1651:
1626:
1503:
1412:
1313:
1097:
580:
455:
431:
396:
107:
99:
1661:
1512:
30:
2787:
2781:
2775:
2769:
2328:
Vogel E, Köcher M (March 1986). "Porphycene—a Novel
Porphin Isomer".
1228:
1162:
534:
443:
231:
135:
127:
2411:
962:
Porphyrin-based compounds are of interest as possible components of
921:
2544:
1273:
1215:
1108:
several versions of chlorophyll exist (sidechain; exception being
880:
522:
447:
226:
protons, porphyrins bind metal ions in the N4 "pocket". The metal
29:
2398:
Dougherty TJ (2001). "Basic principles of photodynamic therapy".
16:
Heterocyclic organic compound with four modified pyrrole subunits
2765:
1437:(2011). "Origin of aromatic character in porphyrinoid systems".
1295:
1000:
560:
513:
335:
281:
119:
2563:
1625:
Senge MO, Ryan AA, Letchford KA, MacGowan SA, Mielke T (2014).
227:
64:
520:
associated with the deficiency of each enzyme is also shown:
1157:
biosynthetic intermediate en route to cofactor F430 and B12
58:
1059:
Light-activated porphyrin. Monatomic oxygen. Cellular aging
1535:
Walker FA, Simonis U (2011). "Iron
Porphyrin Chemistry".
1243:
shape as shown in figure. Porphycenes showed interesting
415:, as well as the α-proteobacteria group of bacteria, the
67:
1627:"Chlorophylls, Symmetry, Chirality, and Photosynthesis"
1874:
Wormald R, Evans J, Smeeth L, Henshaw K (July 2007).
79:
70:
61:
1537:
Encyclopedia of Inorganic and Bioinorganic Chemistry
643:
aminolevulinic acid dehydratase deficiency porphyria
478:. This pathway is known as the C5 or Beale pathway.
55:
3023:
3000:
2979:
2904:
2858:
2849:
2819:
2756:
2747:
2719:
2710:
2669:
2647:
2598:
2260:Walker CH, Silby RM, Hopkin SP, Peakall DB (2012).
52:
1247:behavior and found versatile compound towards the
2285:Scott LJ, Goa KL (February 2000). "Verteporfin".
938:Porphyrins have been evaluated in the context of
118:, an essential member of the porphyrin group is
1568:Jentzen W, Ma JG, Shelnutt JA (February 1998).
427:(δ-ALA, 5-ALA or dALA) by the reaction of the
2575:
350:A macrocycle of 40 porphyrin molecules, model
8:
454:(except for the α-proteobacteria group) and
2160:Bajju GD, Ahmed A, Devi G (December 2019).
1883:The Cochrane Database of Systematic Reviews
605:X-linked dominant protoporphyria, X-linked
481:Two molecules of dALA are then combined by
466:. The enzymes involved in this pathway are
222:Concomitant with the displacement of two N-
2855:
2753:
2716:
2653:
2606:
2582:
2568:
2560:
2264:. Boca Raton, FL: CRC Press. p. 182.
1674:
1672:
1173:several variants of B12 exist (sidechain)
1148:Important cofactor in sulfur assimilation
2545:Journal of Porphyrins and Phthalocyanines
2400:Journal of Porphyrins and Phthalocyanines
2236:
2187:
2177:
2048:Journal of Porphyrins and Phthalocyanines
1986:
1937:
1660:
1650:
1601:
1511:
1439:Journal of Porphyrins and Phthalocyanines
1383:
900:A common synthesis for porphyrins is the
265:Representative porphyrins and derivatives
1076:
530:
476:glutamate-1-semialdehyde 2,1-aminomutase
362:A macrocycle of 40 porphyrin molecules,
250:
244:
240:
2516:Angewandte Chemie International Edition
2427:Angewandte Chemie International Edition
1912:Price M, Terlecky SR, Kessel D (2009).
1350:
1014:
280:are common in nature, the precursor to
263:
138:, an essential porphyrin derivative is
1278:Various reported Isomers of porphyrin
912:process starting with pyrrole and an
411:such as animals, insects, fungi, and
7:
2127:Bioorganic & Medicinal Chemistry
1401:Organic & Biomolecular Chemistry
1306:Porphyrin coordinated to magnesium:
1300:A heme-containing group of enzymes:
889:-tetratolylporphyrin, prepared from
218:Transition metal porphyrin complexes
1364:Journal of Experimental Nanoscience
1358:Rayati S, Malekmohammadi S (2016).
715:congenital erythropoietic porphyria
338:, a complex of a protoporphyrin IX.
126:, whose functions include carrying
1323:, which is coordinated to a cobalt
1312:The one-carbon-shorter analogues:
722:Uroporphyrinogen III decarboxylase
501:to form the circular tetrapyrrole
14:
1863:. Vol. 27. pp. 303–416.
1337:Nitrogen-substituted porphyrins:
958:Molecular electronics and sensors
102:subunits interconnected at their
2357:The Journal of Organic Chemistry
2299:10.2165/00002512-200016020-00005
2293:(2): 139–146, discussion 146–8.
1930:10.1111/j.1751-1097.2009.00589.x
1208:is a benzoporphyrin derivative.
1052:
1033:
1017:
920:
355:
343:
327:
308:
289:
269:
48:
2229:10.1021/acs.bioconjchem.1c00123
1918:Photochemistry and Photobiology
1470:The Online Etymology Dictionary
1294:Porphyrin coordinated to iron:
1891:10.1002/14651858.CD002030.pub3
1545:10.1002/9781119951438.eibc0104
1227:The first synthetic porphyrin
762:Coproporphyrinogen III oxidase
755:hepatoerythropoietic porphyria
383:, coal, or sedimentary rocks.
1:
2550:Handbook of Porphyrin Science
1861:Handbook of Porphyrin Science
1594:10.1016/S0006-3495(98)74000-7
1385:10.1080/17458080.2016.1179802
1288:A porphyrin-related disease:
1212:Non-natural porphyrin isomers
991:Heme biosynthesis is used as
863:erythropoietic protoporphyria
686:Uroporphyrinogen III synthase
191:consist of a square planar MN
1759:10.1016/0146-6380(89)90038-7
1724:10.1016/j.tetlet.2003.08.007
679:acute intermittent porphyria
157:The parent of porphyrins is
98:, composed of four modified
2262:Principles of Ecotoxicology
1979:10.1021/acs.chemrev.5b00244
1332:methyl coenzyme M reductase
3098:
1251:. This inspired Vogel and
1189:highly reduced macrocycle
968:dye-sensitized solar cells
874:
798:Protoporphyrinogen oxidase
215:
165:. One result of the large
122:, which is a component of
18:
2656:
2609:
2179:10.1186/s13065-019-0523-9
2139:10.1016/j.bmc.2015.03.043
2061:10.1142/S1088424610002689
1451:10.1142/S1088424611004063
1222:McMurry coupling reaction
1133:
893:and pyrrole in refluxing
791:hereditary coproporphyria
2796:Magnesium protoporphyrin
483:porphobilinogen synthase
468:glutamyl-tRNA synthetase
464:glutamate-1-semialdehyde
19:Not to be confused with
3072:Photosynthetic pigments
2369:10.1021/acs.joc.1c02652
2096:10.1126/science.1209688
2012:Chemical Communications
1831:-tetraphenylporphine".
1679:Kadish KM, ed. (1999).
1492:Chemical Communications
1464:Harper D, Buglione DC.
1137:(an isobacteriochlorin)
974:Biological applications
751:porphyria cutanea tarda
734:Coproporphyrinogen III
472:glutamyl-tRNA reductase
212:Complexes of porphyrins
142:, which is involved in
37:, the parent porphyrin.
2528:10.1002/anie.199407791
2439:10.1002/anie.199316001
2342:10.1002/anie.198602571
2217:Bioconjugate Chemistry
1682:The Porphyrin Handbook
1279:
1224:
929:Potential applications
897:
885:Brilliant crystals of
774:Protoporphyrinogen IX
770:Coproporphyrinogen III
589:δ-Aminolevulinic acid
528:
462:via glutamyl-tRNA and
458:, it is produced from
407:In non-photosynthetic
249:] → M(porphyrinate)L
38:
2896:Protoporphyrinogen IX
1277:
1269:N-confused porphyrins
1219:
1047:-tetraphenylporphyrin
1028:-tetraphenylporphyrin
964:molecular electronics
884:
806:Protoporphyrinogen IX
698:Uroporphyrinogen III
662:Hydroxymethyl bilane
622:δ-Aminolevulinic acid
526:
425:δ-aminolevulinic acid
33:
2989:Bacteriochlorophyll
2968:Bacteriochlorophyll
1739:Organic Geochemistry
1445:(11n12): 1093–1115.
1249:photodynamic therapy
1024:Lewis structure for
944:macular degeneration
940:photodynamic therapy
934:Photodynamic therapy
891:4-methylbenzaldehyde
871:Laboratory synthesis
730:Uroporphyrinogen III
694:Hydroxymethyl bilane
607:sideroblastic anemia
503:uroporphyrinogen III
495:hydroxymethyl bilane
423:is the formation of
392:organic geochemistry
316:Tetraphenylporphyrin
3002:Isobacteriochlorins
2837:Protochlorophyllide
2811:Zinc protoporphyrin
2501:10.1021/ja00081a047
2088:2011Sci...334..629Y
2018:(81): 10069–10086.
1973:(18): 10261–10306.
1846:10.1021/jo01288a053
1814:10.1021/ja01313a510
1787:10.1021/ja01295a027
1751:1989OrGeo..14..585M
1712:Tetrahedron Letters
1643:2014Symm....6..781S
1586:1998BpJ....74..753J
1580:(2 Pt 1): 753–763.
1574:Biophysical Journal
1498:(96): 17031–17063.
1376:2016JENan..11..872R
1235:, and the central N
1121:bacteriochlorophyll
1079:
827:variegate porphyria
334:Simplified view of
243:porphyrin + [ML
189:Porphyrin complexes
2882:Coproporphyrinogen
2024:10.1039/c2cc31279d
1652:10.3390/sym6030781
1504:10.1039/C5CC06254C
1413:10.1039/C4OB01018C
1280:
1225:
1077:
902:Rothemund reaction
898:
877:Rothemund reaction
810:Protoporphyrin IX
529:
371:Ancient porphyrins
297:Octaethylporphyrin
39:
3049:
3048:
3045:
3044:
3041:
3040:
2845:
2844:
2801:Protoporphyrin IX
2729:Adenosylcobalamin
2706:
2705:
2702:
2701:
2679:Phycoerythrobilin
2460:(19): 2919–2923.
2454:Angewandte Chemie
2330:Angewandte Chemie
2287:Drugs & Aging
2271:978-1-4665-0260-4
2133:(10): 2529–2537.
2082:(6056): 629–634.
1808:(10): 2010–2011.
1775:J. Am. Chem. Soc.
1407:(32): 6145–6150.
1193:
1192:
868:
867:
842:Protoporphyrin IX
507:protoporphyrin IX
440:citric acid cycle
278:protoporphyrin IX
167:conjugated system
148:electron transfer
96:organic compounds
86:) are a group of
3089:
3077:Chelating agents
3015:Sirohydrochlorin
2981:Bacteriochlorins
2868:Uroporphyrinogen
2856:
2754:
2717:
2661:Phytochromobilin
2654:
2607:
2584:
2577:
2570:
2561:
2532:
2531:
2511:
2505:
2504:
2489:J. Am. Chem. Soc
2484:
2478:
2477:
2449:
2443:
2442:
2422:
2416:
2415:
2395:
2389:
2388:
2363:(5): 2721–2729.
2352:
2346:
2345:
2325:
2319:
2318:
2282:
2276:
2275:
2257:
2251:
2250:
2240:
2223:(6): 1067–1077.
2208:
2202:
2201:
2191:
2181:
2157:
2151:
2150:
2122:
2116:
2115:
2071:
2065:
2064:
2042:
2036:
2035:
2007:
2001:
2000:
1990:
1967:Chemical Reviews
1958:
1952:
1951:
1941:
1924:(6): 1491–1496.
1909:
1903:
1902:
1880:
1871:
1865:
1864:
1856:
1850:
1849:
1824:
1818:
1817:
1802:J. Am. Chem. Soc
1797:
1791:
1790:
1769:
1763:
1762:
1734:
1728:
1727:
1707:
1701:
1700:
1676:
1667:
1666:
1664:
1654:
1622:
1616:
1615:
1605:
1565:
1559:
1558:
1532:
1526:
1525:
1515:
1487:
1481:
1480:
1478:
1476:
1466:"porphyria (n.)"
1461:
1455:
1454:
1431:
1425:
1424:
1396:
1390:
1389:
1387:
1355:
1135:sirohydrochlorin
1080:
1056:
1037:
1021:
924:
626:Porphobilinogen
531:
497:(HMB), which is
359:
347:
331:
312:
293:
273:
257:
180: 'purple'.
144:light harvesting
113:
82:
77:
76:
73:
72:
69:
66:
63:
60:
57:
54:
3097:
3096:
3092:
3091:
3090:
3088:
3087:
3086:
3052:
3051:
3050:
3037:
3019:
2996:
2975:
2900:
2851:
2841:
2821:Phytoporphyrins
2815:
2758:Protoporphyrins
2743:
2739:Methylcobalamin
2698:
2694:Phycoviolobilin
2684:Phycocyanobilin
2665:
2643:
2624:Stercobilinogen
2602:
2594:
2588:
2541:
2536:
2535:
2513:
2512:
2508:
2486:
2485:
2481:
2451:
2450:
2446:
2424:
2423:
2419:
2412:10.1002/jpp.328
2397:
2396:
2392:
2354:
2353:
2349:
2327:
2326:
2322:
2284:
2283:
2279:
2272:
2259:
2258:
2254:
2210:
2209:
2205:
2159:
2158:
2154:
2124:
2123:
2119:
2073:
2072:
2068:
2044:
2043:
2039:
2009:
2008:
2004:
1960:
1959:
1955:
1911:
1910:
1906:
1885:(3): CD002030.
1878:
1873:
1872:
1868:
1858:
1857:
1853:
1826:
1825:
1821:
1799:
1798:
1794:
1771:
1770:
1766:
1736:
1735:
1731:
1709:
1708:
1704:
1697:
1689:. p. 381.
1678:
1677:
1670:
1624:
1623:
1619:
1567:
1566:
1562:
1555:
1534:
1533:
1529:
1489:
1488:
1484:
1474:
1472:
1463:
1462:
1458:
1433:
1432:
1428:
1398:
1397:
1393:
1357:
1356:
1352:
1347:
1330:active site in
1321:
1302:Cytochrome P450
1285:
1239:Cavity forms a
1238:
1214:
1198:
1117:bacteriochlorin
1072:
1067:
1065:Related species
1060:
1057:
1048:
1038:
1029:
1022:
1013:
1005:ALA dehydratase
989:
976:
960:
936:
931:
879:
873:
658:Porphobilinogen
614:ALA dehydratase
487:porphobilinogen
405:
373:
366:
360:
351:
348:
339:
332:
323:
321:
313:
304:
302:
294:
285:
276:Derivatives of
274:
261:
255:
248:
242:
238:
220:
214:
203:
199:
194:
186:
111:
80:
51:
47:
28:
17:
12:
11:
5:
3095:
3093:
3085:
3084:
3079:
3074:
3069:
3064:
3054:
3053:
3047:
3046:
3043:
3042:
3039:
3038:
3036:
3035:
3029:
3027:
3021:
3020:
3018:
3017:
3012:
3006:
3004:
2998:
2997:
2995:
2994:
2985:
2983:
2977:
2976:
2974:
2973:
2965:
2947:
2929:
2914:Chlorophyllide
2910:
2908:
2902:
2901:
2899:
2898:
2893:
2879:
2864:
2862:
2860:Porphyrinogens
2853:
2847:
2846:
2843:
2842:
2840:
2839:
2834:
2825:
2823:
2817:
2816:
2814:
2813:
2808:
2803:
2798:
2793:
2762:
2760:
2751:
2745:
2744:
2742:
2741:
2736:
2734:Cyanocobalamin
2731:
2725:
2723:
2714:
2708:
2707:
2704:
2703:
2700:
2699:
2697:
2696:
2691:
2686:
2681:
2675:
2673:
2667:
2666:
2664:
2663:
2657:
2651:
2645:
2644:
2642:
2641:
2636:
2631:
2626:
2621:
2616:
2610:
2604:
2596:
2595:
2589:
2587:
2586:
2579:
2572:
2564:
2558:
2557:
2552:
2547:
2540:
2539:External links
2537:
2534:
2533:
2506:
2479:
2444:
2417:
2390:
2347:
2320:
2277:
2270:
2252:
2203:
2152:
2117:
2066:
2055:(9): 759–792.
2037:
2002:
1953:
1904:
1866:
1851:
1819:
1792:
1781:(4): 625–627.
1764:
1729:
1702:
1695:
1668:
1637:(3): 781–843.
1617:
1560:
1553:
1527:
1482:
1456:
1426:
1391:
1349:
1348:
1346:
1343:
1342:
1341:
1339:phthalocyanine
1335:
1324:
1319:
1310:
1304:
1298:
1292:
1284:
1281:
1236:
1213:
1210:
1202:benzoporphyrin
1197:
1194:
1191:
1190:
1187:
1184:
1179:
1175:
1174:
1171:
1168:
1165:
1159:
1158:
1155:
1153:
1150:
1149:
1146:
1143:
1138:
1131:
1130:
1127:
1124:
1118:
1114:
1113:
1106:
1103:
1100:
1094:
1093:
1090:
1087:
1084:
1071:
1068:
1066:
1063:
1062:
1061:
1058:
1051:
1049:
1039:
1032:
1030:
1023:
1016:
1012:
1009:
997:organochlorine
988:
985:
975:
972:
959:
956:
935:
932:
930:
927:
926:
925:
895:propionic acid
875:Main article:
872:
869:
866:
865:
860:
855:
850:
847:
844:
839:
838:Mitochondrion
836:
834:Ferrochelatase
830:
829:
824:
819:
814:
811:
808:
803:
802:Mitochondrion
800:
794:
793:
788:
783:
778:
775:
772:
767:
766:Mitochondrion
764:
758:
757:
748:
743:
738:
735:
732:
727:
724:
718:
717:
712:
707:
702:
701:10q25.2-q26.3
699:
696:
691:
688:
682:
681:
676:
671:
666:
663:
660:
655:
652:
646:
645:
640:
635:
630:
627:
624:
619:
616:
610:
609:
603:
598:
593:
590:
587:
578:
577:Mitochondrion
575:
569:
568:
563:
558:
553:
548:
545:
540:
537:
516:database. The
419:for porphyrin
417:committed step
404:
401:
372:
369:
368:
367:
361:
354:
352:
349:
342:
340:
333:
326:
324:
319:
314:
307:
305:
300:
295:
288:
286:
275:
268:
266:
259:
258:
216:Main article:
213:
210:
201:
197:
192:
185:
182:
152:photosynthesis
15:
13:
10:
9:
6:
4:
3:
2:
3094:
3083:
3080:
3078:
3075:
3073:
3070:
3068:
3065:
3063:
3060:
3059:
3057:
3034:
3033:Cofactor F430
3031:
3030:
3028:
3026:
3022:
3016:
3013:
3011:
3008:
3007:
3005:
3003:
2999:
2993:
2992:
2987:
2986:
2984:
2982:
2978:
2972:
2971:
2966:
2963:
2962:
2957:
2956:
2951:
2948:
2945:
2944:
2939:
2938:
2933:
2930:
2927:
2926:
2921:
2920:
2915:
2912:
2911:
2909:
2907:
2903:
2897:
2894:
2891:
2887:
2883:
2880:
2877:
2873:
2869:
2866:
2865:
2863:
2861:
2857:
2854:
2848:
2838:
2835:
2833:
2832:
2827:
2826:
2824:
2822:
2818:
2812:
2809:
2807:
2804:
2802:
2799:
2797:
2794:
2791:
2790:
2785:
2784:
2779:
2778:
2773:
2772:
2767:
2764:
2763:
2761:
2759:
2755:
2752:
2750:
2746:
2740:
2737:
2735:
2732:
2730:
2727:
2726:
2724:
2722:
2718:
2715:
2713:
2709:
2695:
2692:
2690:
2689:Phycourobilin
2687:
2685:
2682:
2680:
2677:
2676:
2674:
2672:
2668:
2662:
2659:
2658:
2655:
2652:
2650:
2646:
2640:
2637:
2635:
2632:
2630:
2627:
2625:
2622:
2620:
2617:
2615:
2612:
2611:
2608:
2605:
2601:
2597:
2593:
2592:tetrapyrroles
2585:
2580:
2578:
2573:
2571:
2566:
2565:
2562:
2556:
2553:
2551:
2548:
2546:
2543:
2542:
2538:
2529:
2525:
2521:
2517:
2510:
2507:
2502:
2498:
2494:
2490:
2483:
2480:
2475:
2471:
2467:
2463:
2459:
2455:
2448:
2445:
2440:
2436:
2432:
2428:
2421:
2418:
2413:
2409:
2405:
2401:
2394:
2391:
2386:
2382:
2378:
2374:
2370:
2366:
2362:
2358:
2351:
2348:
2343:
2339:
2335:
2331:
2324:
2321:
2316:
2312:
2308:
2304:
2300:
2296:
2292:
2288:
2281:
2278:
2273:
2267:
2263:
2256:
2253:
2248:
2244:
2239:
2234:
2230:
2226:
2222:
2218:
2214:
2207:
2204:
2199:
2195:
2190:
2185:
2180:
2175:
2171:
2167:
2166:BMC Chemistry
2163:
2156:
2153:
2148:
2144:
2140:
2136:
2132:
2128:
2121:
2118:
2113:
2109:
2105:
2101:
2097:
2093:
2089:
2085:
2081:
2077:
2070:
2067:
2062:
2058:
2054:
2050:
2049:
2041:
2038:
2033:
2029:
2025:
2021:
2017:
2013:
2006:
2003:
1998:
1994:
1989:
1984:
1980:
1976:
1972:
1968:
1964:
1957:
1954:
1949:
1945:
1940:
1935:
1931:
1927:
1923:
1919:
1915:
1908:
1905:
1900:
1896:
1892:
1888:
1884:
1877:
1870:
1867:
1862:
1855:
1852:
1847:
1843:
1839:
1836:
1835:
1834:J. Org. Chem.
1830:
1823:
1820:
1815:
1811:
1807:
1803:
1796:
1793:
1788:
1784:
1780:
1777:
1776:
1768:
1765:
1760:
1756:
1752:
1748:
1744:
1740:
1733:
1730:
1725:
1721:
1717:
1713:
1706:
1703:
1698:
1696:9780123932006
1692:
1688:
1684:
1683:
1675:
1673:
1669:
1663:
1658:
1653:
1648:
1644:
1640:
1636:
1632:
1628:
1621:
1618:
1613:
1609:
1604:
1599:
1595:
1591:
1587:
1583:
1579:
1575:
1571:
1564:
1561:
1556:
1554:9781119951438
1550:
1546:
1542:
1538:
1531:
1528:
1523:
1519:
1514:
1509:
1505:
1501:
1497:
1493:
1486:
1483:
1471:
1467:
1460:
1457:
1452:
1448:
1444:
1440:
1436:
1430:
1427:
1422:
1418:
1414:
1410:
1406:
1402:
1395:
1392:
1386:
1381:
1377:
1373:
1369:
1365:
1361:
1354:
1351:
1344:
1340:
1336:
1333:
1329:
1328:Cofactor F430
1325:
1322:
1315:
1311:
1309:
1305:
1303:
1299:
1297:
1293:
1291:
1287:
1286:
1282:
1276:
1272:
1270:
1266:
1265:isoporphycene
1262:
1258:
1254:
1250:
1246:
1245:photophysical
1242:
1234:
1230:
1223:
1218:
1211:
1209:
1207:
1203:
1195:
1188:
1185:
1183:
1182:Cofactor F430
1180:
1177:
1176:
1172:
1169:
1166:
1164:
1161:
1160:
1156:
1154:
1152:
1151:
1147:
1144:
1142:
1139:
1136:
1132:
1128:
1125:
1122:
1119:
1116:
1115:
1111:
1110:chlorophyll c
1107:
1104:
1101:
1099:
1096:
1095:
1091:
1088:
1086:Cofactor name
1085:
1083:N4-macrocycle
1082:
1081:
1078:Caption text
1075:
1069:
1064:
1055:
1050:
1046:
1042:
1036:
1031:
1027:
1020:
1015:
1010:
1008:
1006:
1002:
998:
994:
986:
984:
982:
973:
971:
969:
965:
957:
955:
951:
949:
945:
941:
933:
928:
923:
919:
918:
917:
915:
911:
907:
903:
896:
892:
888:
883:
878:
870:
864:
861:
859:
856:
854:
851:
848:
845:
843:
840:
837:
835:
832:
831:
828:
825:
823:
820:
818:
815:
812:
809:
807:
804:
801:
799:
796:
795:
792:
789:
787:
784:
782:
779:
776:
773:
771:
768:
765:
763:
760:
759:
756:
752:
749:
747:
744:
742:
739:
736:
733:
731:
728:
725:
723:
720:
719:
716:
713:
711:
708:
706:
703:
700:
697:
695:
692:
689:
687:
684:
683:
680:
677:
675:
672:
670:
667:
664:
661:
659:
656:
653:
651:
650:PBG deaminase
648:
647:
644:
641:
639:
636:
634:
631:
628:
625:
623:
620:
617:
615:
612:
611:
608:
604:
602:
599:
597:
594:
591:
588:
586:
582:
579:
576:
574:
571:
570:
567:
564:
562:
559:
557:
554:
552:
549:
546:
544:
541:
538:
536:
533:
532:
525:
521:
519:
515:
510:
508:
504:
500:
496:
492:
488:
484:
479:
477:
473:
469:
465:
461:
460:glutamic acid
457:
453:
449:
445:
441:
437:
433:
430:
426:
422:
418:
414:
410:
402:
400:
398:
393:
390:The field of
388:
386:
382:
378:
370:
365:
358:
353:
346:
341:
337:
330:
325:
317:
311:
306:
298:
292:
287:
283:
279:
272:
267:
264:
262:
253:
247:
237:
236:
235:
233:
229:
225:
219:
211:
209:
207:
190:
183:
181:
179:
175:
172:
168:
164:
160:
155:
153:
149:
145:
141:
137:
133:
129:
125:
121:
117:
109:
105:
101:
97:
93:
89:
85:
84:
75:
45:
41:
36:
32:
26:
22:
3062:Biomolecules
2990:
2969:
2960:
2954:
2942:
2936:
2924:
2918:
2830:
2829:Chlorophyll
2788:
2782:
2776:
2770:
2748:
2634:Urobilinogen
2519:
2515:
2509:
2492:
2488:
2482:
2457:
2453:
2447:
2433:(11): 1600.
2430:
2426:
2420:
2403:
2399:
2393:
2360:
2356:
2350:
2333:
2329:
2323:
2290:
2286:
2280:
2261:
2255:
2220:
2216:
2206:
2169:
2165:
2155:
2130:
2126:
2120:
2079:
2075:
2069:
2052:
2046:
2040:
2015:
2011:
2005:
1970:
1966:
1956:
1921:
1917:
1907:
1882:
1869:
1860:
1854:
1837:
1832:
1828:
1822:
1805:
1801:
1795:
1778:
1773:
1767:
1742:
1738:
1732:
1718:(39): 7253.
1715:
1711:
1705:
1681:
1634:
1630:
1620:
1577:
1573:
1563:
1536:
1530:
1495:
1491:
1485:
1475:14 September
1473:. Retrieved
1469:
1459:
1442:
1438:
1429:
1404:
1400:
1394:
1367:
1363:
1353:
1316:, including
1268:
1264:
1260:
1256:
1232:
1226:
1201:
1199:
1073:
1044:
1043:readout for
1025:
990:
980:
977:
961:
952:
937:
906:condensation
899:
886:
585:succinyl CoA
573:ALA synthase
511:
480:
436:succinyl-CoA
421:biosynthesis
406:
403:Biosynthesis
399:porphyrins.
389:
374:
260:
251:
245:
223:
221:
187:
177:
174:
156:
124:hemoproteins
88:heterocyclic
43:
42:
40:
2932:Chlorophyll
2671:Phycobilins
2649:Phytobilins
2629:Stercobilin
1370:(11): 872.
1308:chlorophyll
1261:porphycerin
1257:corrphycene
1206:verteporfin
1167:vitamin B12
1102:chlorophyll
948:verteporfin
491:deamination
256:+ 4 L + 2 H
206:Chlorophyll
140:chlorophyll
132:bloodstream
116:vertebrates
92:macrocyclic
3082:Porphyrins
3067:Metabolism
3056:Categories
2950:Pheophytin
2852:porphyrins
2806:Pterobilin
2749:Porphyrins
2721:Corrinoids
2712:Macrocycle
2619:Biliverdin
2522:(7): 779.
2495:(2): 767.
2406:(2): 105.
2336:(3): 257.
1840:(2): 476.
1745:(6): 585.
1662:2262/73843
1513:2262/75305
1345:References
1233:porphycene
999:exposure,
987:Toxicology
551:Chromosome
499:hydrolysed
429:amino acid
409:eukaryotes
385:Abelsonite
178:(porphyra)
106:atoms via
44:Porphyrins
2614:Bilirubin
2590:Types of
2385:246165814
2315:260491296
2172:(1): 15.
1318:vitamin B
1290:porphyria
1241:rectangle
1196:Synthetic
1126:magnesium
1123:(in part)
1105:magnesium
1070:In nature
1003:inhibits
993:biomarker
910:oxidation
543:Substrate
539:Location
518:porphyria
438:from the
381:oil shale
377:crude oil
364:STM image
184:Structure
110:bridges (
25:Porphyran
3025:Corphins
3010:Siroheme
2906:Chlorins
2639:Urobilin
2603:(Linear)
2474:10540393
2377:35061396
2307:10755329
2247:34033716
2198:31384764
2147:25863493
2112:28058582
2104:22053043
2032:22649792
1997:26317756
1948:19659920
1899:17636693
1687:Elsevier
1631:Symmetry
1522:26482230
1421:25002069
1314:corroles
1283:See also
1141:siroheme
1092:comment
1007:enzyme.
981:in vitro
914:aldehyde
853:4.99.1.1
849:18q21.3
741:4.1.1.37
726:Cytosol
705:4.2.1.75
690:Cytosol
669:2.5.1.61
665:11q23.3
654:Cytosol
633:4.2.1.24
618:Cytosol
596:2.3.1.37
566:Disorder
547:Product
485:to give
452:bacteria
413:protozoa
163:aromatic
159:porphine
104:α carbon
35:Porphine
21:Perforin
2850:Reduced
2600:Bilanes
2238:8485325
2189:6661832
2084:Bibcode
2076:Science
1988:6011754
1939:2783742
1747:Bibcode
1639:Bibcode
1612:9533688
1603:1302556
1582:Bibcode
1435:Lash TD
1372:Bibcode
1253:Sessler
1178:corphin
1098:chlorin
1011:Gallery
817:1.3.3.4
781:1.3.3.3
592:3p21.1
581:Glycine
456:archaea
432:glycine
397:vanadyl
176:πορφύρα
130:in the
108:methine
100:pyrrole
83:-fər-in
2472:
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2030:
1995:
1985:
1946:
1936:
1897:
1693:
1610:
1600:
1551:
1520:
1419:
1229:isomer
1186:nickel
1170:cobalt
1163:corrin
1041:UV–vis
946:using
858:177000
822:600923
786:121300
746:176100
710:606938
674:176000
638:125270
601:125290
535:Enzyme
474:, and
444:plants
232:ligand
136:plants
128:oxygen
114:). In
2381:S2CID
2311:S2CID
2108:S2CID
1879:(PDF)
1334:(MCR)
1089:metal
846:Heme
813:1q22
777:3q12
737:1p34
629:9q34
493:into
448:algae
442:. In
434:with
282:hemes
173:
171:Greek
134:. In
2766:Heme
2470:PMID
2373:PMID
2303:PMID
2266:ISBN
2243:PMID
2194:PMID
2143:PMID
2100:PMID
2028:PMID
1993:PMID
1944:PMID
1895:PMID
1829:meso
1691:ISBN
1608:PMID
1549:ISBN
1518:PMID
1477:2014
1417:PMID
1296:heme
1145:iron
1045:meso
1026:meso
1001:lead
908:and
887:meso
561:OMIM
514:OMIM
336:heme
146:and
120:heme
112:=CH−
2890:III
2876:III
2524:doi
2497:doi
2493:116
2462:doi
2435:doi
2408:doi
2365:doi
2338:doi
2295:doi
2233:PMC
2225:doi
2184:PMC
2174:doi
2135:doi
2092:doi
2080:334
2057:doi
2020:doi
1983:PMC
1975:doi
1971:115
1934:PMC
1926:doi
1887:doi
1842:doi
1810:doi
1783:doi
1755:doi
1720:doi
1657:hdl
1647:doi
1598:PMC
1590:doi
1541:doi
1508:hdl
1500:doi
1447:doi
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1380:doi
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