35:
329:
341:
442:
481:
357:
1846:
580:
of THC is difficult due to high costs and low yields. Therefore, the use of THCA synthase for the production of THC has been explored, as CBGA is easy to synthesize and THCA readily decarboxylates to form THC. Biosynthesis of THCA by expressing THCA synthase in organisms has been attempted in
612:
Shoyama Y, Tamada T, Kurihara K, Takeuchi A, Taura F, Arai S, Blaber M, Shoyama Y, Morimoto S, Kuroki R (October 2012). "Structure and function of ∆1-tetrahydrocannabinolic acid (THCA) synthase, the enzyme controlling the psychoactivity of
Cannabis sativa".
1113:
Zirpel B, Stehle F, Kayser O (September 2015). "Production of Δ9-tetrahydrocannabinolic acid from cannabigerolic acid by whole cells of Pichia (Komagataella) pastoris expressing Δ9-tetrahydrocannabinolic acid synthase from
Cannabis sativa L".
328:
258:. Therefore, THCA synthase is considered to be a key enzyme controlling cannabis psychoactivity. Polymorphisms of THCA synthase result in varying levels of THC in Cannabis plants, resulting in
648:
Staginnus C, Zörntlein S, de Meijer E (July 2014). "A PCR marker linked to a THCA synthase polymorphism is a reliable tool to discriminate potentially THC-rich plants of
Cannabis sativa L".
691:
Kojoma M, Seki H, Yoshida S, Muranaka T (June 2006). "DNA polymorphisms in the tetrahydrocannabinolic acid (THCA) synthase gene in "drug-type" and "fiber-type" Cannabis sativa L".
429:
1505:
1368:
1510:
340:
177:
519:. Because these products are toxic to the plant, THCA synthase is secreted into the trichome storage cavity. THCA also acts as a necrosis-inducing factor by opening
1258:
1206:
Lange K, Schmid A, Julsing MK (October 2015). "Δ(9)-Tetrahydrocannabinolic acid synthase production in Pichia pastoris enables chemical synthesis of cannabinoids".
763:"The gene controlling marijuana psychoactivity: molecular cloning and heterologous expression of Delta1-tetrahydrocannabinolic acid synthase from Cannabis sativa L"
308:
and is covalently bound to FAD. Domain II comprises five alpha helices surrounded by eight beta sheets. Enzymes that share similar amino acid sequences include the
196:
520:
322:
with neighboring amino acid main chains and side chains. The co-crystallization of THCA synthase with substrate or product has not been accomplished yet.
853:"Tetrahydrocannabinolic acid synthase, the enzyme controlling marijuana psychoactivity, is secreted into the storage cavity of the glandular trichomes"
1373:
734:
Taura F, Morimoto S, Shoyama Y, Mechoulam R (1995). "First direct evidence for the mechanism of Δ-tetrahydrocannabinolic acid biosynthesis".
534:, the principal psychoactive component of cannabis. Further degradation by temperature, auto-oxidation, and light forms cannabinol. THC and other
894:"Identification and characterization of cannabinoids that induce cell death through mitochondrial permeability transition in Cannabis leaf cells"
461:
group by a tyrosine residue. The monoterpene moiety in CBGA is then positioned to complete cyclization into THCA. Oxidation of reduced FAD by O
34:
1251:
334:
FAD cofactor (in green) is located between domain I and domain II of THCA synthase. Alpha helices are cyan and beta sheets are magenta.
1565:
1532:
189:
1339:
286:
1244:
581:
bacteria, insects, and tobacco plants with limited success. Production of THCA on a milligram scale has been demonstrated in
156:
132:
1721:
549:
is a flavoprotein that catalyzes a similar oxidative cyclization of CPGA into CBDA, the dominant cannabinoid constituent of
1159:"Synthesis of (-)-Delta9-trans-tetrahydrocannabinol: stereocontrol via Mo-catalyzed asymmetric allylic alkylation reaction"
1871:
318:
The FAD moiety is the location of enzymatic activity and is covalently bound to His114 and Cys176. FAD is also bound by
1527:
546:
446:
369:
297:
229:
20:
1836:
293:
1706:
1822:
1809:
1796:
1783:
1770:
1757:
1744:
1478:
1429:
1406:
1383:
1349:
1321:
1281:
1716:
150:
1670:
1613:
1487:
1419:
1363:
1272:
278:
55:
1387:
137:
1618:
372:
405:
group compared to CBGA, suggesting that the carboxyl group of CBGA is necessary for the reaction to occur.
289:
414:
201:
1639:
1558:
394:
237:
125:
1711:
538:
are well-known to reduce nausea and vomiting and stimulate hunger, particularly in patients undergoing
1294:
531:
241:
393:
of cannabigerolic acid (CBGA). Similar cyclization reactions occur in monoterpene biosynthesis from
1675:
1517:
1492:
802:
Shoyama Y, Takeuchi A, Taura F, Tamada T, Adachi M, Kuroki R, Shoyama Y, Morimoto S (August 2005).
233:
153:
761:
Sirikantaramas S, Morimoto S, Shoyama Y, Ishikawa Y, Wada Y, Shoyama Y, Taura F (September 2004).
77:
1866:
1608:
1497:
1139:
1071:"Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa"
1051:
892:
Morimoto S, Tanaka Y, Sasaki K, Tanaka H, Fukamizu T, Shoyama Y, Shoyama Y, Taura F (July 2007).
716:
673:
577:
390:
1223:
1188:
1131:
1092:
1043:
1008:
956:
915:
874:
833:
784:
708:
665:
630:
512:
466:
282:
245:
144:
1654:
1649:
1623:
1551:
1358:
1215:
1178:
1170:
1123:
1082:
1035:
998:
990:
946:
905:
864:
823:
815:
804:"Crystallization of Delta1-tetrahydrocannabinolic acid (THCA) synthase from Cannabis sativa"
774:
743:
700:
657:
622:
569:
568:
Demand is high for pharmaceutical grade THC and other cannabinoids due to interest in their
545:
Similar enzymes to THCA synthase catalyze the formation of other cannabinoids. For example,
441:
113:
1701:
1685:
1598:
583:
527:
499:
402:
383:
259:
254:
249:
851:
Sirikantaramas S, Taura F, Tanaka Y, Ishikawa Y, Morimoto S, Shoyama Y (September 2005).
89:
480:
60:
1850:
1739:
1680:
1268:
1236:
1183:
1158:
1003:
978:
828:
803:
172:
315:(BBE), glucooligosaccharide oxidase (GOOX), and aclacinomycin oxidoreductase (AknOx).
1860:
1644:
1603:
1334:
1069:
Taura F, Sirikantaramas S, Shoyama Y, Yoshikai K, Shoyama Y, Morimoto S (June 2007).
504:
458:
454:
319:
1143:
720:
704:
677:
484:
Reaction mechanism of THCA synthase. Modified from
Shoyama et al. J. Mol. Bio. 2012.
1593:
1446:
1055:
539:
516:
398:
365:
356:
309:
1219:
1087:
1070:
523:, inhibiting mitochondrial viability and resulting in senescence in leaf tissues.
360:
Chemical structure of cannabigerolic acid (CBGA), the substrate for THCA synthase.
1817:
1752:
1588:
1396:
557:
535:
387:
301:
1845:
346:
FAD (in green) is covalently bound to histidine 114 and cysteine 176 (in pink).
1433:
1410:
1285:
1127:
819:
626:
397:, but are not oxidative. THCA synthase exhibits no catalytic activity against
305:
1791:
1765:
661:
376:
312:
225:
1227:
1192:
1135:
1096:
1047:
1012:
919:
910:
893:
878:
837:
788:
779:
762:
712:
669:
634:
994:
960:
935:"Tetrahydrocannabinolic acid, a genuine substance of tetrahydrocannabinol"
869:
852:
494:
951:
934:
747:
101:
1437:
120:
1174:
1026:
Guzmán M (October 2003). "Cannabinoids: potential anticancer agents".
40:
1804:
1574:
221:
184:
96:
84:
72:
1039:
933:
Yamauchi T, Shoyama Y, Aramaki H, Azuma T, Nishioka I (July 1967).
1778:
1466:
1461:
1456:
1325:
479:
440:
380:
355:
1451:
1309:
1304:
1299:
550:
263:
108:
1547:
1240:
453:
A hydride is transferred from CBGA to reduce FAD, concerted by
300:
positioned between the two domains. Domain I comprises eight
1543:
418:
296:
is divided into two domains (domains I and II), with a
292:
increases the total mass to approximately 74 kDa. The
1834:
417:
1730:
1694:
1663:
1632:
1581:
1477:
1428:
1405:
1382:
1348:
1320:
1280:
972:
970:
556:. CBDA undergoes a similar decarboxylation to form
195:
183:
171:
166:
143:
131:
119:
107:
95:
83:
71:
66:
54:
49:
27:
1369:4-Hydroxy-3-methylbut-2-enyl diphosphate reductase
423:
1108:
1106:
607:
605:
603:
601:
599:
1559:
1252:
281:(~500 amino acids) monomeric enzyme with the
8:
493:THCA synthase is expressed in the glandular
252:, which is produced from various strains of
1481:: Acting on X-H and Y-H to form an X-Y bond
521:mitochondrial permeability transition pores
214:Tetrahydrocannabinolic acid (THCA) synthase
1566:
1552:
1544:
1259:
1245:
1237:
408:The overall chemical reaction is: CBGA + O
163:
33:
1182:
1086:
1002:
950:
909:
868:
827:
778:
572:, but is stymied by legal regulations of
416:
587:yeast cells in two independent studies.
530:of THCA during storage or smoking forms
1841:
1374:7-Hydroxymethyl chlorophyll a reductase
595:
324:
939:Chemical & Pharmaceutical Bulletin
576:cultivation in many countries. Direct
503:. THCA synthase may contribute to the
218:Δ-tetrahydrocannabinolic acid synthase
24:
7:
1523:Tetrahydrocannabinolic acid synthase
28:Tetrahydrocannibinolic acid synthase
898:The Journal of Biological Chemistry
767:The Journal of Biological Chemistry
424:{\displaystyle \rightleftharpoons }
547:cannabidiolic acid (CBDA) synthase
447:tetrahydrocannabinolic acid (THCA)
14:
983:Cannabis and Cannabinoid Research
979:"9-Tetrahydrocannabinolic Acid A"
370:flavin adenine dinucleotide (FAD)
298:flavin adenine dinucleotide (FAD)
1844:
1533:Dichlorochromopyrrolate synthase
1157:Trost BM, Dogra K (March 2007).
808:Acta Crystallographica Section F
339:
327:
1340:(Methionine synthase) reductase
705:10.1016/j.forsciint.2005.07.005
449:, the product of THCA synthase.
693:Forensic Science International
1:
1511:(-)-bisdechlorogeodin-forming
1506:(+)-bisdechlorogeodin-forming
1220:10.1016/j.jbiotec.2015.06.425
1088:10.1016/j.febslet.2007.05.043
511:plants by producing THCA and
1352:: Acting on CH or CH2 groups
977:Moreno-Sanz G (2016-06-01).
650:Journal of Forensic Sciences
615:Journal of Molecular Biology
1528:Cannabidiolic acid synthase
857:Plant & Cell Physiology
236:(CBGA). THCA is the direct
21:Cannabidiolic acid synthase
1888:
242:tetrahydrocannabinol (THC)
18:
1722:Michaelis–Menten kinetics
1128:10.1007/s10529-015-1853-x
820:10.1107/S1744309105023365
627:10.1016/j.jmb.2012.06.030
570:potential therapeutic use
162:
32:
1614:Diffusion-limited enzyme
1488:Isopenicillin N synthase
1420:Nitrogenase (flavodoxin)
1364:Ribonucleotide reductase
1208:Journal of Biotechnology
662:10.1111/1556-4029.12448
313:berberine bridge enzyme
1028:Nature Reviews. Cancer
911:10.1074/jbc.M700133200
780:10.1074/jbc.M403693200
485:
450:
445:Chemical structure of
425:
361:
290:N-linked glycosylation
277:THCA synthase is a 60
1707:Eadie–Hofstee diagram
1640:Allosteric regulation
1116:Biotechnology Letters
995:10.1089/can.2016.0008
483:
444:
426:
395:geranyl pyrophosphate
359:
1872:Tetrahydrocannabinol
1717:Lineweaver–Burk plot
1409:: Acting on reduced
1388:iron–sulfur proteins
1295:Superoxide dismutase
467:hydrogen peroxide (H
415:
1518:Aureusidin synthase
1493:Columbamine oxidase
952:10.1248/cpb.15.1075
748:10.1021/ja00143a024
540:cancer chemotherapy
489:Biological function
234:cannabigerolic acid
1676:Enzyme superfamily
1609:Enzyme promiscuity
1502:Sulochrin oxidase
1498:Reticuline oxidase
870:10.1093/pcp/pci166
578:chemical synthesis
486:
451:
421:
362:
352:Reaction mechanism
294:tertiary structure
287:Post-translational
1832:
1831:
1541:
1540:
1175:10.1021/ol063022k
814:(Pt 8): 799–801.
742:(38): 9766–9767.
515:, which are both
513:hydrogen peroxide
364:THCA synthase, a
283:isoelectric point
228:the formation of
211:
210:
207:
206:
126:metabolic pathway
1879:
1849:
1848:
1840:
1712:Hanes–Woolf plot
1655:Enzyme activator
1650:Enzyme inhibitor
1624:Enzyme catalysis
1568:
1561:
1554:
1545:
1359:Xanthine oxidase
1261:
1254:
1247:
1238:
1232:
1231:
1203:
1197:
1196:
1186:
1154:
1148:
1147:
1110:
1101:
1100:
1090:
1066:
1060:
1059:
1023:
1017:
1016:
1006:
974:
965:
964:
954:
930:
924:
923:
913:
904:(28): 20739–51.
889:
883:
882:
872:
848:
842:
841:
831:
799:
793:
792:
782:
773:(38): 39767–74.
758:
752:
751:
736:J. Am. Chem. Soc
731:
725:
724:
688:
682:
681:
645:
639:
638:
609:
430:
428:
427:
422:
401:, which lacks a
343:
331:
244:, the principal
224:responsible for
164:
43:
37:
25:
1887:
1886:
1882:
1881:
1880:
1878:
1877:
1876:
1857:
1856:
1855:
1843:
1835:
1833:
1828:
1740:Oxidoreductases
1726:
1702:Enzyme kinetics
1690:
1686:List of enzymes
1659:
1628:
1599:Catalytic triad
1577:
1572:
1542:
1537:
1473:
1424:
1401:
1378:
1344:
1316:
1276:
1269:oxidoreductases
1265:
1235:
1205:
1204:
1200:
1163:Organic Letters
1156:
1155:
1151:
1112:
1111:
1104:
1081:(16): 2929–34.
1068:
1067:
1063:
1040:10.1038/nrc1188
1025:
1024:
1020:
976:
975:
968:
932:
931:
927:
891:
890:
886:
850:
849:
845:
801:
800:
796:
760:
759:
755:
733:
732:
728:
699:(2–3): 132–40.
690:
689:
685:
647:
646:
642:
611:
610:
597:
593:
584:Pichia pastoris
566:
528:decarboxylation
500:Cannabis sativa
491:
474:
470:
464:
438:
434:
413:
412:
411:
354:
347:
344:
335:
332:
275:
255:Cannabis sativa
45:
39:
23:
17:
12:
11:
5:
1885:
1883:
1875:
1874:
1869:
1859:
1858:
1854:
1853:
1830:
1829:
1827:
1826:
1813:
1800:
1787:
1774:
1761:
1748:
1734:
1732:
1728:
1727:
1725:
1724:
1719:
1714:
1709:
1704:
1698:
1696:
1692:
1691:
1689:
1688:
1683:
1678:
1673:
1667:
1665:
1664:Classification
1661:
1660:
1658:
1657:
1652:
1647:
1642:
1636:
1634:
1630:
1629:
1627:
1626:
1621:
1616:
1611:
1606:
1601:
1596:
1591:
1585:
1583:
1579:
1578:
1573:
1571:
1570:
1563:
1556:
1548:
1539:
1538:
1536:
1535:
1530:
1525:
1520:
1515:
1514:
1513:
1508:
1500:
1495:
1490:
1484:
1482:
1475:
1474:
1472:
1471:
1470:
1469:
1464:
1459:
1454:
1443:
1441:
1426:
1425:
1423:
1422:
1416:
1414:
1403:
1402:
1400:
1399:
1393:
1391:
1380:
1379:
1377:
1376:
1371:
1366:
1361:
1355:
1353:
1346:
1345:
1343:
1342:
1337:
1331:
1329:
1318:
1317:
1315:
1314:
1313:
1312:
1307:
1302:
1291:
1289:
1278:
1277:
1266:
1264:
1263:
1256:
1249:
1241:
1234:
1233:
1198:
1149:
1122:(9): 1869–75.
1102:
1061:
1034:(10): 745–55.
1018:
989:(1): 124–130.
966:
925:
884:
863:(9): 1578–82.
843:
794:
753:
726:
683:
640:
594:
592:
589:
565:
562:
526:Non-enzymatic
490:
487:
472:
468:
462:
436:
432:
420:
409:
353:
350:
349:
348:
345:
338:
336:
333:
326:
320:hydrogen bonds
274:
271:
209:
208:
205:
204:
199:
193:
192:
187:
181:
180:
175:
169:
168:
160:
159:
148:
141:
140:
135:
129:
128:
123:
117:
116:
111:
105:
104:
99:
93:
92:
87:
81:
80:
75:
69:
68:
64:
63:
58:
52:
51:
47:
46:
38:
30:
29:
15:
13:
10:
9:
6:
4:
3:
2:
1884:
1873:
1870:
1868:
1865:
1864:
1862:
1852:
1847:
1842:
1838:
1824:
1820:
1819:
1814:
1811:
1807:
1806:
1801:
1798:
1794:
1793:
1788:
1785:
1781:
1780:
1775:
1772:
1768:
1767:
1762:
1759:
1755:
1754:
1749:
1746:
1742:
1741:
1736:
1735:
1733:
1729:
1723:
1720:
1718:
1715:
1713:
1710:
1708:
1705:
1703:
1700:
1699:
1697:
1693:
1687:
1684:
1682:
1681:Enzyme family
1679:
1677:
1674:
1672:
1669:
1668:
1666:
1662:
1656:
1653:
1651:
1648:
1646:
1645:Cooperativity
1643:
1641:
1638:
1637:
1635:
1631:
1625:
1622:
1620:
1617:
1615:
1612:
1610:
1607:
1605:
1604:Oxyanion hole
1602:
1600:
1597:
1595:
1592:
1590:
1587:
1586:
1584:
1580:
1576:
1569:
1564:
1562:
1557:
1555:
1550:
1549:
1546:
1534:
1531:
1529:
1526:
1524:
1521:
1519:
1516:
1512:
1509:
1507:
1504:
1503:
1501:
1499:
1496:
1494:
1491:
1489:
1486:
1485:
1483:
1480:
1476:
1468:
1465:
1463:
1460:
1458:
1455:
1453:
1450:
1449:
1448:
1445:
1444:
1442:
1439:
1435:
1431:
1427:
1421:
1418:
1417:
1415:
1412:
1408:
1404:
1398:
1395:
1394:
1392:
1389:
1385:
1381:
1375:
1372:
1370:
1367:
1365:
1362:
1360:
1357:
1356:
1354:
1351:
1347:
1341:
1338:
1336:
1335:Ceruloplasmin
1333:
1332:
1330:
1327:
1323:
1319:
1311:
1308:
1306:
1303:
1301:
1298:
1297:
1296:
1293:
1292:
1290:
1287:
1283:
1279:
1274:
1270:
1262:
1257:
1255:
1250:
1248:
1243:
1242:
1239:
1229:
1225:
1221:
1217:
1213:
1209:
1202:
1199:
1194:
1190:
1185:
1180:
1176:
1172:
1168:
1164:
1160:
1153:
1150:
1145:
1141:
1137:
1133:
1129:
1125:
1121:
1117:
1109:
1107:
1103:
1098:
1094:
1089:
1084:
1080:
1076:
1072:
1065:
1062:
1057:
1053:
1049:
1045:
1041:
1037:
1033:
1029:
1022:
1019:
1014:
1010:
1005:
1000:
996:
992:
988:
984:
980:
973:
971:
967:
962:
958:
953:
948:
945:(7): 1075–6.
944:
940:
936:
929:
926:
921:
917:
912:
907:
903:
899:
895:
888:
885:
880:
876:
871:
866:
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847:
844:
839:
835:
830:
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821:
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805:
798:
795:
790:
786:
781:
776:
772:
768:
764:
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741:
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730:
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718:
714:
710:
706:
702:
698:
694:
687:
684:
679:
675:
671:
667:
663:
659:
656:(4): 919–26.
655:
651:
644:
641:
636:
632:
628:
624:
621:(1): 96–105.
620:
616:
608:
606:
604:
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596:
590:
588:
586:
585:
579:
575:
571:
563:
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541:
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455:deprotonation
448:
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371:
367:
358:
351:
342:
337:
330:
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323:
321:
316:
314:
311:
310:flavoproteins
307:
303:
302:alpha helices
299:
295:
291:
288:
284:
280:
272:
270:
268:
265:
261:
257:
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251:
248:component of
247:
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102:NiceZyme view
100:
98:
94:
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88:
86:
82:
79:
76:
74:
70:
65:
62:
59:
57:
53:
48:
42:
36:
31:
26:
22:
1818:Translocases
1815:
1802:
1789:
1776:
1763:
1753:Transferases
1750:
1737:
1594:Binding site
1522:
1447:Glutaredoxin
1432:: Acting on
1386:: Acting on
1324:: Oxidizing
1284:: Acting on
1211:
1207:
1201:
1169:(5): 861–3.
1166:
1162:
1152:
1119:
1115:
1078:
1075:FEBS Letters
1074:
1064:
1031:
1027:
1021:
986:
982:
942:
938:
928:
901:
897:
887:
860:
856:
846:
811:
807:
797:
770:
766:
756:
739:
735:
729:
696:
692:
686:
653:
649:
643:
618:
614:
582:
573:
567:
564:Significance
552:
544:
536:cannabinoids
525:
508:
505:self-defense
498:
492:
452:
407:
399:cannabigerol
366:flavoprotein
363:
317:
276:
266:
264:"fiber-type"
253:
246:psychoactive
217:
213:
212:
90:BRENDA entry
1589:Active site
1397:Nitrogenase
1288:as acceptor
558:cannabidiol
551:fiber-type
388:monoterpene
384:cyclization
269:varieties.
260:"drug-type"
216:(full name
78:IntEnz view
50:Identifiers
1861:Categories
1792:Isomerases
1766:Hydrolases
1633:Regulation
1434:phosphorus
1411:flavodoxin
1286:superoxide
1275:1.15–1.21)
591:References
306:beta sheet
304:and eight
226:catalyzing
147:structures
114:KEGG entry
19:See also:
1867:EC 1.21.3
1671:EC number
1440:in donors
1390:as donors
1214:: 68–76.
574:C. sativa
553:C. sativa
517:cytotoxic
495:trichomes
465:produces
419:⇌
381:oxidative
368:, uses a
273:Structure
267:C. sativa
238:precursor
67:Databases
1695:Kinetics
1619:Cofactor
1582:Activity
1413:as donor
1228:26197418
1193:17266321
1144:16544089
1136:25994576
1097:17544411
1048:14570037
1013:28861488
920:17513301
879:16024552
838:16511162
789:15190053
721:38866142
713:16143478
678:29683549
670:24579739
635:22766313
509:Cannabis
459:hydroxyl
431:THCA + H
403:carboxyl
377:catalyze
373:cofactor
285:at 6.4.
250:cannabis
220:) is an
202:proteins
190:articles
178:articles
151:RCSB PDB
61:1.21.3.7
1851:Biology
1805:Ligases
1575:Enzymes
1438:arsenic
1184:2597621
1056:7868655
1004:5549534
961:5583149
829:1952348
386:of the
138:profile
121:MetaCyc
44:
1837:Portal
1779:Lyases
1267:Other
1226:
1191:
1181:
1142:
1134:
1095:
1054:
1046:
1011:
1001:
959:
918:
877:
836:
826:
787:
719:
711:
676:
668:
633:
391:moiety
222:enzyme
185:PubMed
167:Search
157:PDBsum
97:ExPASy
85:BRENDA
73:IntEnz
56:EC no.
16:Enzyme
1731:Types
1467:GLRX5
1462:GLRX3
1457:GLRX2
1326:metal
1140:S2CID
1052:S2CID
717:S2CID
674:S2CID
457:of a
232:from
133:PRIAM
1823:list
1816:EC7
1810:list
1803:EC6
1797:list
1790:EC5
1784:list
1777:EC4
1771:list
1764:EC3
1758:list
1751:EC2
1745:list
1738:EC1
1479:1.21
1452:GLRX
1430:1.20
1407:1.19
1384:1.18
1350:1.17
1328:ions
1322:1.16
1310:SOD3
1305:SOD2
1300:SOD1
1282:1.15
1224:PMID
1189:PMID
1132:PMID
1093:PMID
1044:PMID
1009:PMID
957:PMID
916:PMID
875:PMID
834:PMID
785:PMID
709:PMID
666:PMID
631:PMID
379:the
262:and
230:THCA
197:NCBI
154:PDBe
109:KEGG
41:3VTE
1436:or
1216:doi
1212:211
1179:PMC
1171:doi
1124:doi
1083:doi
1079:581
1036:doi
999:PMC
991:doi
947:doi
906:doi
902:282
865:doi
824:PMC
816:doi
775:doi
771:279
744:doi
740:117
701:doi
697:159
658:doi
623:doi
619:423
532:THC
507:of
497:of
375:to
279:kDa
240:of
173:PMC
145:PDB
1863::
1273:EC
1222:.
1210:.
1187:.
1177:.
1165:.
1161:.
1138:.
1130:.
1120:37
1118:.
1105:^
1091:.
1077:.
1073:.
1050:.
1042:.
1030:.
1007:.
997:.
985:.
981:.
969:^
955:.
943:15
941:.
937:.
914:.
900:.
896:.
873:.
861:46
859:.
855:.
832:.
822:.
812:61
810:.
806:.
783:.
769:.
765:.
738:.
715:.
707:.
695:.
672:.
664:.
654:59
652:.
629:.
617:.
598:^
560:.
542:.
477:.
1839::
1825:)
1821:(
1812:)
1808:(
1799:)
1795:(
1786:)
1782:(
1773:)
1769:(
1760:)
1756:(
1747:)
1743:(
1567:e
1560:t
1553:v
1271:(
1260:e
1253:t
1246:v
1230:.
1218::
1195:.
1173::
1167:9
1146:.
1126::
1099:.
1085::
1058:.
1038::
1032:3
1015:.
993::
987:1
963:.
949::
922:.
908::
881:.
867::
840:.
818::
791:.
777::
750:.
746::
723:.
703::
680:.
660::
637:.
625::
475:)
473:2
471:O
469:2
463:2
437:2
435:O
433:2
410:2
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