449:
469:, and is catalyzed by 2-oxoglutarate-dependent dioxygenases. When molecules are hydroxylated, they become more water‐soluble, which affects their structure and function. It can take place on several amino acids, like lysine, asparagine, aspartate and histidine, but the most frequently hydroxylated amino acid residue in human
544:
organisms to help them control excess amounts of phenylalanine residues. Hydroxylation of tyrosine residues is also very vital in living organisms because hydroxylation at C-3 of tyrosine creates 3,4- dihydroxy phenylalanine (DOPA), which is a precursor to hormones and can be converted into dopamine.
543:
Several endogenous proteins contain hydroxyphenylalanine and hydroxytyrosine residues. These residues are formed due to the hydroxylation of phenylalanine and tyrosine, a process in which the hydroxylation converts phenylalanine residues into tyrosine residues. This is very important in living
94:
Installing hydroxyl groups into organic compounds can be affected by various metal catalysts. Many such catalysts are biomimetic, i.e. they are inspired by or intended to mimic enzymes such as cytochrome P450.
387:
524:(vitamin C) to return the iron to its reduced state. Deprivation of ascorbate leads to deficiencies in proline hydroxylation, which leads to less stable collagen, which can manifest itself as the disease
247:
599:
Middleton, Elliott Jr; Kandaswami, Chithan; Theoharides, Theoharis C. (2000). "The
Effects of Plant Flavonoids on Mammalian Cells: Implications for Inflammation, Heart Disease, and Cancer".
485:
at almost every 3rd residue in its amino acid sequence. Collagen consists of both 3‐hydroxyproline and 4‐hydroxyproline residues. Hydroxylation occurs at the γ-C atom, forming
1022:
489:(Hyp), which stabilizes the secondary structure of collagen due to the strong electronegative effects of oxygen. Proline hydroxylation is also a vital component of
442:
1853:
1015:
399:
itself is a slow and unselective hydroxylating agent, catalysts are required to accelerate the pace of the process and to introduce selectivity.
989:
873:
1008:
253:
626:
Jia, Chengguo; Kitamura, Tsugio; Fujiwara, Yuzo (2001). "Catalytic
Functionalization of Arenes and Alkanes via C−H Bond Activation".
783:
1848:
558:
497:. In some cases, proline may be hydroxylated instead on its β-C atom. Lysine may also be hydroxylated on its δ-C atom, forming
466:
1035:
1685:
158:
402:
Hydroxylation is often the first step in the degradation of organic compounds in air. Hydroxylation is important in
661:
Kolb, Hartmuth C.; Vannieuwenhze, Michael S.; Sharpless, K. Barry (1994). "Catalytic
Asymmetric Dihydroxylation".
1725:
1136:
1031:
568:
563:
109:
1000:
494:
453:
456:
that explains many iron-catalyzed hydroxylations: H-atom abstraction, oxygen rebound, alcohol decomplexation.
1779:
778:
Nelson, D. L.; Cox, M. M. "Lehninger, Principles of
Biochemistry" 3rd Ed. Worth Publishing: New York, 2000.
415:
1663:
937:
Hausinger RP (January–February 2004). "Fe(II)/α-ketoglutarate-dependent hydroxylases and related enzymes".
1054:
578:
One example of non-biological hydroxylation is the hydrogen peroxide hydroxylation of phenol to form
573:
509:
505:
100:
1069:
1141:
513:
427:
1490:
1480:
1384:
1234:
962:
879:
761:
553:
517:
1338:
1224:
1183:
985:
954:
919:
869:
835:
817:
779:
726:
643:
608:
490:
117:
1641:
1619:
1518:
1437:
1328:
1305:
1229:
1201:
946:
909:
861:
825:
809:
753:
716:
708:
697:"Beyond ferryl-mediated hydroxylation: 40 years of the rebound mechanism and C–H activation"
670:
635:
438:
66:
1752:
1452:
1343:
1219:
1178:
441:, hundreds of variations of which are known. Other hydroxylating agents include flavins,
152:
bond. Typical stoichiometries for the hydroxylation of a generic hydrocarbon are these:
1614:
1508:
1485:
1427:
1277:
1259:
1146:
1112:
830:
797:
721:
696:
692:
486:
482:
403:
58:
914:
897:
796:
Zurlo, Giada; Guo, Jianping; Takada, Mamoru; Wei, Wenyi; Zhang, Qing (December 2016).
1842:
1633:
1578:
1560:
1475:
1470:
1417:
1366:
1323:
1244:
1188:
1092:
883:
521:
498:
407:
966:
896:
Holmgren, Steven K; Bretscher, Lynn E; Taylor, Kimberly M; Raines, Ronald T (1999).
765:
1432:
1249:
1064:
1049:
579:
533:
133:
798:"New Insights into Protein Hydroxylation and Its Important Role in Human Diseases"
744:
Cerniglia, Carl E. (1992). "Biodegradation of polycyclic aromatic hydrocarbons".
1554:
1513:
1442:
1407:
1402:
1361:
1333:
1300:
1282:
1254:
1107:
1097:
1087:
1059:
813:
865:
858:
Co- and Post-Translational
Modifications of Therapeutic Antibodies and Proteins
516:, respectively. These reactions require iron (as well as molecular oxygen and
1794:
1700:
1677:
1673:
1629:
1593:
1570:
1353:
1157:
1123:
1079:
950:
712:
411:
31:
821:
1823:
1736:
1546:
1465:
1412:
1376:
1315:
1292:
1239:
1170:
1102:
423:
54:
42:
35:
958:
923:
839:
730:
647:
612:
17:
1811:
1807:
1803:
1740:
1713:
1655:
1606:
1602:
1500:
1447:
1269:
1211:
1193:
504:
These three reactions are catalyzed by very large, multi-subunit enzymes
478:
674:
1771:
1763:
1744:
1717:
1528:
757:
474:
470:
445:(2-oxoglutarate-dependent dioxygenases), and some diiron hydroxylases.
431:
639:
148:
bond is converted to an alcohol by insertion of an oxygen atom into a
1815:
1767:
1709:
1651:
1394:
1166:
529:
525:
137:
121:
448:
80:
refers to the location of hydroxy groups on a molecule or material.
1460:
1131:
537:
481:
makes up about 25–35% of the protein in our bodies and contains a
447:
419:
536:
to combat scurvy on long ocean voyages; hence, they were called "
382:{\displaystyle {\ce {R3C-H + O2 + 2e- + 2H+ -> R3C-OH + H2O}}}
113:
27:
Chemical reaction which adds an –OH group to an organic compound
1004:
980:
Voet, Donald; Voet, Judith G.; Pratt, Charlotte W. (2016).
30:
Hydroxylation and hydroxylases are not to be confused with
372:
345:
295:
268:
224:
204:
177:
1753:
4-(p-hydroxybenzylidene)-5-imidazolinone (HBI) formation
802:
Biochimica et
Biophysica Acta (BBA) - Reviews on Cancer
856:
T. Shantha Raju (2019), "Hydroxylation of
Proteins",
528:. Since citrus fruits are rich in vitamin C, British
256:
161:
76:
refers to the number of OH groups in a molecule. The
1802:
1792:
1762:
1735:
1708:
1698:
1672:
1650:
1628:
1601:
1591:
1569:
1545:
1527:
1499:
1393:
1375:
1352:
1314:
1291:
1268:
1210:
1165:
1155:
1122:
1078:
1042:
136:, hydroxylation reactions are often facilitated by
1726:p-Hydroxybenzylidene-imidazolinone (HBI) formation
381:
241:
434:) are activated or deactivated by hydroxylation.
242:{\displaystyle {\ce {2R3C-H + O2 -> 2R3C-OH}}}
414:) products that are more readily removed by the
98:Whereas many hydroxylations insert O atoms into
437:The principal hydroxylation agent in nature is
1016:
112:is such a reaction: it converts alkenes into
53:(i) most commonly, hydroxylation describes a
8:
1686:Tryptophan tryptophylquinone (TTQ) formation
860:, John Wiley & Sons, pp. 119–131,
851:
849:
1799:
1705:
1598:
1162:
1023:
1009:
1001:
465:The hydroxylation of proteins occurs as a
443:alpha-ketoglutarate-dependent hydroxylases
108:OH groups to unsaturated substrates. The
913:
829:
720:
701:Journal of Biological Inorganic Chemistry
371:
366:
351:
344:
339:
326:
321:
309:
304:
294:
289:
274:
267:
262:
257:
255:
230:
223:
218:
213:
203:
198:
183:
176:
171:
166:
162:
160:
395:
1780:Methylidene-imidazolone (MIO) formation
591:
120:, which adds across the double bond of
520:) to carry out the oxidation, and use
1664:Lysine tyrosylquinone (LTQ) formation
686:
684:
116:. The hydroxy groups are provided by
7:
1137:Glycosyl phosphatidylinositol (GPI)
25:
1448:Oxidative deamination to aldehyde
1854:Post-translational modification
1036:posttranslational modifications
559:Cholesterol 7 alpha-hydroxylase
477:. This is due to the fact that
467:post-translational modification
898:"A hyperstable collagen mimic"
410:compounds into water-soluble (
332:
207:
1:
939:Crit. Rev. Biochem. Mol. Biol
915:10.1016/S1074-5521(99)80003-9
628:Accounts of Chemical Research
1255:Topaquinone (TPQ) formation
814:10.1016/j.bbcan.2016.09.004
1870:
982:Principles of Biochemistry
866:10.1002/9781119053354.ch10
57:process that introduces a
29:
1699:Crosslinks between three
1032:Protein primary structure
951:10.1080/10409230490440541
713:10.1007/s00775-016-1414-3
569:Phenylalanine hydroxylase
495:hypoxia inducible factors
110:Sharpless dihydroxylation
1793:Crosslinks between four
454:oxygen rebound mechanism
128:Biological hydroxylation
90:Synthetic hydroxylations
78:pattern of hydroxylation
1849:Organic redox reactions
1592:Crosslinks between two
902:Chemistry & Biology
601:Pharmacological Reviews
85:Hydroxylation reactions
74:degree of hydroxylation
1240:Porphyrin ring linkage
984:. Wiley. p. 143.
564:Dopamine β-hydroxylase
457:
383:
243:
104:bonds, some reactions
1301:Succinimide formation
451:
384:
244:
1055:Protein biosynthesis
574:Tyrosine hydroxylase
510:prolyl 3-hydroxylase
506:prolyl 4-hydroxylase
254:
159:
675:10.1021/cr00032a009
514:lysyl 5-hydroxylase
374:
347:
297:
270:
226:
206:
179:
1385:Transglutamination
758:10.1007/BF00129093
458:
406:since it converts
379:
362:
335:
285:
258:
239:
214:
194:
167:
1836:
1835:
1832:
1831:
1788:
1787:
1694:
1693:
1587:
1586:
1339:Polyglutamylation
1225:Dephosphorylation
1184:Dephosphorylation
991:978-1-119-45166-2
875:978-1-119-05335-4
640:10.1021/ar000209h
377:
365:
358:
350:
338:
325:
308:
288:
281:
273:
261:
237:
229:
217:
197:
190:
182:
170:
118:hydrogen peroxide
16:(Redirected from
1861:
1800:
1706:
1642:Sulfilimine bond
1620:ADP-ribosylation
1599:
1519:ADP-ribosylation
1438:ADP-ribosylation
1329:ADP-ribosylation
1306:ADP-ribosylation
1230:ADP-ribosylation
1202:ADP-ribosylation
1163:
1156:Single specific
1025:
1018:
1011:
1002:
996:
995:
977:
971:
970:
934:
928:
927:
917:
893:
887:
886:
853:
844:
843:
833:
793:
787:
776:
770:
769:
752:(2–3): 351–368.
741:
735:
734:
724:
707:(2–3): 185–207.
688:
679:
678:
669:(8): 2483–2547.
663:Chemical Reviews
658:
652:
651:
623:
617:
616:
596:
439:cytochrome P-450
398:
388:
386:
385:
380:
378:
375:
373:
370:
363:
356:
355:
348:
346:
343:
336:
331:
330:
323:
314:
313:
306:
296:
293:
286:
279:
278:
271:
269:
266:
259:
248:
246:
245:
240:
238:
235:
234:
227:
225:
222:
215:
205:
202:
195:
188:
187:
180:
178:
175:
168:
151:
147:
103:
67:organic compound
64:
21:
1869:
1868:
1864:
1863:
1862:
1860:
1859:
1858:
1839:
1838:
1837:
1828:
1784:
1758:
1731:
1690:
1668:
1646:
1624:
1583:
1579:C-mannosylation
1565:
1541:
1523:
1495:
1461:Imine formation
1389:
1371:
1348:
1344:Polyglycylation
1310:
1287:
1264:
1220:Phosphorylation
1206:
1179:Phosphorylation
1151:
1118:
1074:
1038:
1029:
999:
992:
979:
978:
974:
936:
935:
931:
895:
894:
890:
876:
855:
854:
847:
795:
794:
790:
777:
773:
743:
742:
738:
690:
689:
682:
660:
659:
655:
625:
624:
620:
598:
597:
593:
589:
554:17α-Hydroxylase
550:
518:α-ketoglutarate
463:
397:
393:
322:
305:
252:
251:
157:
156:
149:
145:
130:
99:
92:
87:
62:
39:
28:
23:
22:
15:
12:
11:
5:
1867:
1865:
1857:
1856:
1851:
1841:
1840:
1834:
1833:
1830:
1829:
1827:
1826:
1820:
1818:
1797:
1790:
1789:
1786:
1785:
1783:
1782:
1776:
1774:
1760:
1759:
1757:
1756:
1749:
1747:
1733:
1732:
1730:
1729:
1722:
1720:
1703:
1696:
1695:
1692:
1691:
1689:
1688:
1682:
1680:
1670:
1669:
1667:
1666:
1660:
1658:
1648:
1647:
1645:
1644:
1638:
1636:
1626:
1625:
1623:
1622:
1617:
1615:Disulfide bond
1611:
1609:
1596:
1589:
1588:
1585:
1584:
1582:
1581:
1575:
1573:
1567:
1566:
1564:
1563:
1558:
1551:
1549:
1543:
1542:
1540:
1539:
1533:
1531:
1525:
1524:
1522:
1521:
1516:
1511:
1509:Citrullination
1505:
1503:
1497:
1496:
1494:
1493:
1488:
1486:Propionylation
1483:
1478:
1473:
1468:
1463:
1458:
1456:-glycosylation
1450:
1445:
1440:
1435:
1430:
1428:Ubiquitination
1425:
1420:
1415:
1410:
1405:
1399:
1397:
1391:
1390:
1388:
1387:
1381:
1379:
1373:
1372:
1370:
1369:
1364:
1358:
1356:
1350:
1349:
1347:
1346:
1341:
1336:
1331:
1326:
1320:
1318:
1312:
1311:
1309:
1308:
1303:
1297:
1295:
1289:
1288:
1286:
1285:
1280:
1278:Palmitoylation
1274:
1272:
1266:
1265:
1263:
1262:
1260:Detyrosination
1257:
1252:
1250:Flavin linkage
1247:
1242:
1237:
1232:
1227:
1222:
1216:
1214:
1208:
1207:
1205:
1204:
1199:
1191:
1186:
1181:
1175:
1173:
1160:
1153:
1152:
1150:
1149:
1147:Detyrosination
1144:
1139:
1134:
1128:
1126:
1120:
1119:
1117:
1116:
1113:Myristoylation
1110:
1105:
1100:
1095:
1090:
1084:
1082:
1076:
1075:
1073:
1072:
1070:N–O acyl shift
1067:
1062:
1057:
1052:
1046:
1044:
1040:
1039:
1030:
1028:
1027:
1020:
1013:
1005:
998:
997:
990:
972:
929:
888:
874:
845:
808:(2): 208–220.
788:
771:
746:Biodegradation
736:
680:
653:
634:(8): 633–639.
618:
607:(4): 673–751.
590:
588:
585:
584:
583:
576:
571:
566:
561:
556:
549:
546:
487:hydroxyproline
483:hydroxyproline
462:
459:
430:(for example,
404:detoxification
390:
389:
369:
361:
354:
342:
334:
329:
320:
317:
312:
303:
300:
292:
284:
277:
265:
249:
233:
221:
212:
209:
201:
193:
186:
174:
165:
129:
126:
91:
88:
86:
83:
82:
81:
70:
59:hydroxyl group
49:can refer to:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
1866:
1855:
1852:
1850:
1847:
1846:
1844:
1825:
1822:
1821:
1819:
1817:
1813:
1809:
1805:
1801:
1798:
1796:
1791:
1781:
1778:
1777:
1775:
1773:
1769:
1765:
1761:
1755:(chromophore)
1754:
1751:
1750:
1748:
1746:
1742:
1738:
1734:
1728:(chromophore)
1727:
1724:
1723:
1721:
1719:
1715:
1711:
1707:
1704:
1702:
1697:
1687:
1684:
1683:
1681:
1679:
1675:
1671:
1665:
1662:
1661:
1659:
1657:
1653:
1649:
1643:
1640:
1639:
1637:
1635:
1634:Hydroxylysine
1631:
1627:
1621:
1618:
1616:
1613:
1612:
1610:
1608:
1604:
1600:
1597:
1595:
1590:
1580:
1577:
1576:
1574:
1572:
1568:
1562:
1561:Adenylylation
1559:
1556:
1553:
1552:
1550:
1548:
1544:
1538:
1537:Hydroxylation
1535:
1534:
1532:
1530:
1526:
1520:
1517:
1515:
1512:
1510:
1507:
1506:
1504:
1502:
1498:
1492:
1489:
1487:
1484:
1482:
1479:
1477:
1476:Succinylation
1474:
1472:
1471:Carbamylation
1469:
1467:
1464:
1462:
1459:
1457:
1455:
1451:
1449:
1446:
1444:
1441:
1439:
1436:
1434:
1431:
1429:
1426:
1424:
1423:Hydroxylation
1421:
1419:
1418:Adenylylation
1416:
1414:
1411:
1409:
1406:
1404:
1401:
1400:
1398:
1396:
1392:
1386:
1383:
1382:
1380:
1378:
1374:
1368:
1367:Glycosylation
1365:
1363:
1360:
1359:
1357:
1355:
1351:
1345:
1342:
1340:
1337:
1335:
1332:
1330:
1327:
1325:
1324:Carboxylation
1322:
1321:
1319:
1317:
1313:
1307:
1304:
1302:
1299:
1298:
1296:
1294:
1290:
1284:
1281:
1279:
1276:
1275:
1273:
1271:
1267:
1261:
1258:
1256:
1253:
1251:
1248:
1246:
1245:Adenylylation
1243:
1241:
1238:
1236:
1233:
1231:
1228:
1226:
1223:
1221:
1218:
1217:
1215:
1213:
1209:
1203:
1200:
1198:
1196:
1192:
1190:
1189:Glycosylation
1187:
1185:
1182:
1180:
1177:
1176:
1174:
1172:
1168:
1164:
1161:
1159:
1154:
1148:
1145:
1143:
1142:O-methylation
1140:
1138:
1135:
1133:
1130:
1129:
1127:
1125:
1121:
1114:
1111:
1109:
1106:
1104:
1101:
1099:
1096:
1094:
1093:Carbamylation
1091:
1089:
1086:
1085:
1083:
1081:
1077:
1071:
1068:
1066:
1063:
1061:
1058:
1056:
1053:
1051:
1048:
1047:
1045:
1041:
1037:
1033:
1026:
1021:
1019:
1014:
1012:
1007:
1006:
1003:
993:
987:
983:
976:
973:
968:
964:
960:
956:
952:
948:
944:
940:
933:
930:
925:
921:
916:
911:
907:
903:
899:
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837:
832:
827:
823:
819:
815:
811:
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799:
792:
789:
785:
784:1-57259-153-6
781:
775:
772:
767:
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759:
755:
751:
747:
740:
737:
732:
728:
723:
718:
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693:Groves, J. T.
687:
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581:
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547:
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541:
539:
535:
531:
527:
523:
522:ascorbic acid
519:
515:
511:
507:
502:
500:
499:hydroxylysine
496:
493:response via
492:
488:
484:
480:
476:
472:
468:
460:
455:
450:
446:
444:
440:
435:
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107:
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96:
89:
84:
79:
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71:
68:
60:
56:
52:
51:
50:
48:
47:hydroxylation
44:
37:
33:
19:
1536:
1491:Butyrylation
1453:
1422:
1194:
1065:Racemization
1050:Peptide bond
981:
975:
945:(1): 21–68.
942:
938:
932:
908:(2): 63–70.
905:
901:
891:
857:
805:
801:
791:
774:
749:
745:
739:
704:
700:
666:
662:
656:
631:
627:
621:
604:
600:
594:
580:hydroquinone
542:
503:
464:
452:Steps in an
436:
401:
391:
142:hydroxylases
141:
134:biochemistry
131:
105:
97:
93:
77:
73:
46:
40:
1555:Diphthamide
1514:Methylation
1481:Lactylation
1443:Deamination
1433:Sumoylation
1408:Acetylation
1403:Methylation
1362:Deamidation
1334:Methylation
1283:Prenylation
1108:Methylation
1098:Formylation
1088:Acetylation
1060:Proteolysis
691:Huang, X.;
532:were given
461:Of proteins
412:hydrophilic
18:Hydroxylase
1843:Categories
1678:Tryptophan
1674:Tryptophan
1630:Methionine
1571:Tryptophan
1354:Asparagine
1124:C terminus
1080:N terminus
587:References
408:lipophilic
65:) into an
36:hydrolases
32:hydrolysis
1824:Desmosine
1737:Histidine
1557:formation
1547:Histidine
1466:Glycation
1413:Acylation
1377:Glutamine
1316:Glutamate
1293:Aspartate
1235:Sulfation
1171:Threonine
1132:Amidation
1103:Glycation
884:243626930
822:0006-3002
353:−
333:⟶
311:−
276:−
232:−
208:⟶
185:−
72:(ii) the
43:chemistry
1812:Allysine
1808:Allysine
1804:Allysine
1741:Tyrosine
1714:Tyrosine
1656:Tyrosine
1607:Cysteine
1603:Cysteine
1501:Arginine
1270:Cysteine
1212:Tyrosine
967:85784668
959:15121720
924:10021421
840:27663420
766:25516145
731:27909920
695:(2017).
648:11513570
613:11121513
548:Examples
479:collagen
471:proteins
432:steroids
426:. Some
424:excreted
55:chemical
1772:Glycine
1764:Alanine
1745:Glycine
1718:Glycine
1529:Proline
1197:-GlcNAc
1043:General
831:5138100
722:5350257
530:sailors
501:(Hyl).
491:hypoxia
475:proline
416:kidneys
140:called
138:enzymes
122:alkenes
1816:Lysine
1768:Serine
1710:Serine
1652:Lysine
1395:Lysine
1167:Serine
988:
965:
957:
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882:
872:
838:
828:
820:
782:
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729:
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646:
611:
538:limeys
526:scurvy
392:Since
1115:(Gly)
963:S2CID
880:S2CID
762:S2CID
534:limes
428:drugs
420:liver
114:diols
1034:and
986:ISBN
955:PMID
920:PMID
870:ISBN
836:PMID
818:ISSN
806:1866
780:ISBN
727:PMID
644:PMID
609:PMID
512:and
422:and
144:. A
34:and
1795:AAs
1701:AAs
1594:AAs
1158:AAs
947:doi
910:doi
862:doi
826:PMC
810:doi
754:doi
717:PMC
709:doi
671:doi
636:doi
540:".
473:is
418:or
150:C−H
146:C−H
132:In
106:add
101:C−H
63:−OH
41:In
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953:.
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605:52
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508:,
357:OH
236:OH
124:.
45:,
1814:–
1810:–
1806:–
1770:–
1766:–
1743:–
1739:–
1716:–
1712:–
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1654:–
1632:–
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1454:O
1195:O
1169:/
1024:e
1017:t
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969:.
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926:.
912::
906:6
864::
842:.
812::
786:.
768:.
756::
750:3
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711::
677:.
673::
650:.
638::
615:.
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396:2
394:O
376:O
368:2
364:H
360:+
349:C
341:3
337:R
328:+
324:H
319:2
316:+
307:e
302:2
299:+
291:2
287:O
283:+
280:H
272:C
264:3
260:R
228:C
220:3
216:R
211:2
200:2
196:O
192:+
189:H
181:C
173:3
169:R
164:2
69:.
61:(
38:.
20:)
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