645:
815:
450:
983:
1340:
1216:
35:
146:
271:
b: InChI=1S/C35H34N4O6.Mg/c1-7-18-15(3)22-11-23-16(4)20(9-10-28(41)42)32(38-23)30-31(35(44)45-6)34(43)29-17(5)24(39-33(29)30)12-26-19(8-2)21(14-40)27(37-26)13-25(18)36-22;/h7,11-14,16,20,31H,1,8-10H2,2-6H3,(H3,36,37,38,39,40,41,42,43);/q;+2/p-2/t16-,20-,31+;/m0./s1
261:
a: InChI=1S/C35H36N4O5.Mg/c1-8-19-15(3)22-12-24-17(5)21(10-11-28(40)41)32(38-24)30-31(35(43)44-7)34(42)29-18(6)25(39-33(29)30)14-27-20(9-2)16(4)23(37-27)13-26(19)36-22;/h8,12-14,17,21,31H,1,9-11H2,2-7H3,(H3,36,37,38,39,40,41,42);/q;+2/p-2/t17-,21-,31+;/m0./s1
1918:"Origin of the Two Carbonyl Oxygens of Bacteriochlorophyll a. Demonstration of two Different Pathways for the Formation of Ring e in Rhodobacter sphaeroides and Roseobacter denitrificans, and a Common Hydratase Mechanism for 3-acetyl Group Formation"
1322:
are the light harvesting pigments found in photosynthetic bacteria: they do not produce oxygen as a side-product. There are many such structures but all are biosynthetically related by being derived from chlorophyllide
831:
1818:"The Chlorophyll Biosynthetic Enzyme Mg-Protoporphyrin IX Monomethyl Ester (Oxidative) Cyclase (Characterization and Partial Purification from Chlamydomonas reinhardtii and Synechocystis sp. PCC 6803)"
1036:
1957:
Parham, Ramin; Rebeiz, Constantin A. (1992). "Chloroplast biogenesis: [4-vinyl] chlorophyllide a reductase is a divinylchlorophyllide a-specific, NADPH-dependent enzyme".
1516:
1486:
1420:
1269:
1196:
1123:
1080:
1025:
976:
865:
800:
729:
2033:
Muraki N, Nomata J, Ebata K, Mizoguchi T, Shiba T, Tamiaki H, Kurisu G, Fujita Y (May 2010). "X-ray crystal structure of the light-independent protochlorophyllide reductase".
762:
287:
941:
905:
the same overall transformation occurs but the oxygen incorporated into magnesium-protoporphyrin IX 13-monomethyl ester comes from water in the reaction
2312:
482:
818:
The chlorin ring system forms as the esterified propionate sidechain is cyclised on to the main porphyrin ring to form divinylprotochlorophyllide
1865:
Stuart, David; Sandström, Malin; Youssef, Helmy M.; Zakhrabekova, Shakhira; Jensen, Poul Erik; Bollivar, David W.; Hansson, Mats (2020-09-08).
1379:) of the pyrrole ring B, giving the characteristic 18-electron aromatic system of many bacteriochlorophylls. This is carried out by the enzyme
1097:
catalysed by an enzyme which can take a variety of substrates and perform the required vinyl-group reduction, for example in this case
1430:
The next two steps convert the vinyl group first into a 1-hydroxyethyl group and then into the acetyl group of bacteriochlorophyllide
888:
2253:
252:
2086:"Synthesis of chlorophyll b: Localization of chlorophyllide a oxygenase and discovery of a stable radical in the catalytic subunit"
2084:
Eggink, Laura L.; Lobrutto, Russell; Brune, Daniel C.; Brusslan, Judy; Yamasato, Akihiro; Tanaka, Ayumi; Hoober, J Kenneth (2004).
2797:
940:
of the macrocycle is retained. These reactions proceed independently and in some organisms the sequence is reversed. The enzyme
822:
The chlorin ring system features a five-membered carbon ring E is created when one of the propionate groups of the porphyrin is
1446:
1769:"Purification and kinetic characterization of the magnesium protoporphyrin IX methyltransferase from Synechocystis PCC6803"
67:)-3-(2-carboxyethyl)-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-9-vinyl-23,25-didehydrophorbine-23,25-diide
1001:
523:
355:
1539:
2185:
Tsuzuki, Yuki; Tsukatani, Yusuke; Yamakawa, Hisanori; Itoh, Shigeru; Fujita, Yuichi; Yamamoto, Haruki (29 March 2022).
2305:
2137:"Pre-Loading of Chlorophyll Synthase with Tetraprenyl Diphosphate is an Obligatory Step in Chlorophyll Biosynthesis"
588:
into protoporphyrin IX in for example mammals gives haem, the oxygen-carrying cofactor in blood, but plants combine
1435:
1380:
1145:
1090:
In the organisms which use this alternative sequence of reduction steps, the process is completed by the reaction
803:
519:
1450:
1439:
1384:
1238:
1161:
1091:
1044:
994:
949:
906:
835:
770:
675:
2526:
1376:
1746:
1371:
901:
2187:"Effects of Light and Oxygen on Chlorophyll d Biosynthesis in a Marine Cyanobacterium Acaryochloris marina"
2792:
2620:
2298:
1526:
These three enzyme-catalysed reactions can occur in different sequences to produce bacteriochlorophyllide
1365:
925:
696:
566:
1916:
Porra, Robert J.; Schafer, Wolfram; Gad'On, Nasr; Katheder, Ingrid; Drews, Gerhart; Scheer, Hugo (1996).
1501:
1471:
1405:
1254:
1181:
1108:
1065:
1010:
961:
850:
785:
714:
2719:
2698:
2626:
1051:
731:
600:
Details of the late stages of the biosynthetic pathway to chlorophyll differ in the plants (for example
570:
51:
644:
2236:
Senge, Mathias O.; Smith, Kevin M. (2004). "Biosynthesis and
Structures of the Bacteriochlorophylls".
1867:"Aerobic Barley Mg-protoporphyrin IX Monomethyl Ester Cyclase is Powered by Electrons from Ferredoxin"
2616:
2606:
2424:
2330:
2273:
2042:
1666:
1234:
780:
656:
602:
539:
438:
410:
2551:
1538:
is not attached directly: rather, the initial intermediate is the ester with R=geranylgeranyl (from
295:
a: CCC1=C(C)C2=Cc3c(C=C)c(C)c4C=C5(C)(CCC(O)=O)C6=55(n34)n3c(=CC1=25)c(C)c1C(=O)(C(=O)OC)C6=c31
2612:
2567:
2541:
1319:
945:
896:
671:
535:
527:
102:
2690:
2732:
2602:
2167:
2066:
1692:
1635:
414:
2379:
814:
2531:
2459:
2409:
2249:
2218:
2159:
2117:
2058:
2015:
1974:
1939:
1898:
1847:
1798:
1727:
1684:
1627:
1589:
614:
608:
581:
204:
2755:
2745:
2654:
2648:
2598:
2391:
2241:
2208:
2198:
2151:
2107:
2097:
2050:
2005:
1966:
1929:
1888:
1878:
1837:
1829:
1788:
1780:
1719:
1674:
1619:
1581:
986:
The reduction of ring D of protochlorophyllide completes the biosynthesis of chlorophyllide
493:
449:
310:
196:
121:
113:
2711:
2469:
2414:
2354:
2136:
1339:
982:
823:
531:
470:
2046:
1670:
175:
167:
2488:
2464:
2213:
2186:
2010:
1993:
1893:
1866:
1793:
1768:
1531:
399:
349:
2112:
2085:
1842:
1817:
936:
and the second adds two atoms of hydrogen to the pyrrole ring D, although the overall
2786:
2763:
2672:
2666:
2590:
2559:
2419:
1934:
1917:
1710:
Battersby, A. R. (2000). "Tetrapyrroles: the
Pigments of Life. A Millennium review".
884:
624:
555:
511:
430:
392:
385:
238:
1639:
2684:
2364:
2322:
2171:
2070:
1696:
1352:
1307:, both made from corresponding chlorophyllides ultimately made from chlorophyllide
515:
478:
381:
230:
1572:
Willows, Robert D. (2003). "Biosynthesis of chlorophylls from protoporphyrin IX".
1534:
to the final pigments for photosynthesis. The phytyl ester of bacteriochlorophyll
1043:
as its cofactor and is not dependent on light; it performs the a similar reaction
2662:
2359:
1348:
1215:
937:
933:
929:
766:
592:
instead to give, after further transformations, chlorophyll for photosynthesis.
578:
418:
17:
34:
2680:
2536:
2442:
2401:
2349:
1623:
1040:
880:
543:
337:
186:
2240:. Advances in Photosynthesis and Respiration. Vol. 2. pp. 137–151.
2479:
2451:
2344:
2245:
1284:
735:
589:
562:
505:
2222:
2203:
2163:
2121:
2062:
1902:
1851:
1802:
1731:
1631:
1593:
2102:
2019:
1992:
Apel, Klaus; Santel, Hans-Joachim; Redlinger, Tom E.; Falk, Heinz (2005).
1978:
1943:
1883:
1688:
1610:
Bollivar, David W. (2007). "Recent advances in chlorophyll biosynthesis".
838:
761:) ester on one of the propionate groups, which is catalysed by the enzyme
757:
The next step towards the chlorophyllides is the formation of a methyl (CH
2740:
2369:
2290:
2135:
Schmid, H. C.; Rassadina, V.; Oster, U.; Schoch, S.; RĂĽdiger, W. (2002).
1833:
1453:
1442:
909:
574:
551:
490:
461:, the methyl group show in the green box is replaced with a formyl group.
2155:
2054:
1970:
1747:"3,8-divinyl-chlorophyllide a biosynthesis I (aerobic, light-dependent)"
1542:) which is then subject to additional steps as three of the sidechain's
1387:
1241:
1164:
1094:
997:
952:
773:
2636:
1784:
1237:
completes the biosynthesis of chlorophyll a by catalysing the reaction
1047:
827:
678:
664:
216:
2518:
2512:
2506:
2500:
1723:
1679:
1654:
1585:
1543:
1288:
1035:
This reaction is light-dependent but there is an alternative enzyme,
876:
668:
660:
633:
422:
403:
348:
Except where otherwise noted, data are given for materials in their
1994:"The Protochlorophyllide Holochrome of Barley (Hordeum vulgare L.)"
1655:"Biosynthesis of the pigments of life: formation of the macrocycle"
1279:
This forms an ester of the carboxylic acid group in chlorophyllide
920:
Two further transformations are required to produce chlorophyllide
1338:
1214:
981:
830:
rings C and D. A series of chemical steps catalysed by the enzyme
813:
643:
629:
448:
426:
413:
in the final step of the pathway. Thus the main interest in these
406:
157:
145:
134:
1058:
3,8-divinylprotochlorophyllide + reduced ferredoxin + 2 ATP + 2 H
2496:
832:
Magnesium-protoporphyrin IX monomethyl ester (oxidative) cyclase
585:
547:
2294:
844:
Mg-protoporphyrin IX 13-monomethyl ester + 3 NADPH + 3 H + 3 O
653:
1653:
Battersby AR, Fookes CJ, Matcham GW, McDonald E (May 1980).
1363:
is a typical example; its biosynthesis has been studied in
891:: the cyclase protein is named XanL and is encoded by the
510:
In the early steps of the biosynthesis, which starts from
1767:
Shepherd, Mark; Reid, James D.; Hunter, C. Neil (2003).
1505:
1475:
1409:
1258:
1185:
1112:
1069:
1037:
Ferredoxin:protochlorophyllide reductase (ATP-dependent)
1014:
965:
854:
789:
718:
500:
Biosynthesis steps up to formation of protoporphyrin IX
489:) and highlighted in the green box, is replaced with a
667:. The metal is inserted into protoporphyrin IX by the
628:) in which it has been studied. However, although the
596:
Biosynthesis of chlorophyllides from protoporphyrin IX
1504:
1474:
1408:
1257:
1184:
1111:
1068:
1013:
1000:
in which the pyrrole ring D is reduced by the enzyme
964:
853:
788:
717:
636:
vary, the chemical reactions involved are identical.
1494:
3-deacetyl 3-(1-hydroxyethyl)bacteriochlorophyllide
1488:
3-deacetyl 3-(1-hydroxyethyl)bacteriochlorophyllide
1295:
is made by the same enzyme acting on chlorophyllide
2754:
2731:
2710:
2635:
2589:
2580:
2550:
2487:
2478:
2450:
2441:
2400:
2378:
2329:
652:Chlorophyll is characterised by having a magnesium
565:and chlorophyll itself. The next intermediates are
1510:
1480:
1414:
1263:
1190:
1117:
1074:
1019:
970:
859:
794:
723:
237:
229:
1315:Use in the biosynthesis of bacteriochlorophylls
437:is also an intermediate in the biosynthesis of
120:
112:
2306:
2274:"Pathway: bacteriochlorophyll a biosynthesis"
763:Magnesium protoporphyrin IX methyltransferase
753:Esterification of the ring C propionate group
8:
648:Magnesium is inserted into protoporphyrin IX
1152:is the enzyme that converts chlorophyllide
1086:+ oxidized ferredoxin + 2 ADP + 2 phosphate
958:3,8-divinylprotochlorophyllide + NADPH + H
944:converts 3,8-divinylprotochlorophyllide to
2586:
2484:
2447:
2384:
2337:
2313:
2299:
2291:
2267:
2265:
1605:
1603:
942:divinyl chlorophyllide a 8-vinyl-reductase
203:
195:
26:
2212:
2202:
2111:
2101:
2009:
1933:
1892:
1882:
1841:
1792:
1678:
1503:
1473:
1460:3-deacetyl 3-vinylbacteriochlorophyllide
1426:+ 2 oxidized ferredoxin + ADP + phosphate
1422:3-deacetyl 3-vinylbacteriochlorophyllide
1407:
1256:
1183:
1110:
1067:
1012:
963:
867:divinylprotochlorophyllide + 3 NADP + 5 H
852:
787:
716:
1816:Bollivar DW, Beale SI (September 1996).
1567:
1565:
1563:
1561:
1559:
1375:. The first step is the reduction (with
1351:or 1-hydroxyethyl group in place of the
826:to the carbon atom linking the original
1555:
1211:Use in the biosynthesis of chlorophylls
802:Mg-protoporphyrin IX 13-methyl ester +
292:
257:
1447:bacteriochlorophyllide a dehydrogenase
879:the electrons are provided by reduced
1335:: bacteriochlorin ring and sidechains
274:Key: QPDWBRHRBKXUNS-IEEIVXFASA-L
264:Key: ANWUQYTXRXCEMZ-NYABAGMLSA-L
174:
166:
7:
2276:. MetaCyc Metabolic Pathway Database
1749:. MetaCyc Metabolic Pathway Database
1347:(R=H). Earlier intermediates have a
1299:. The same is known for chlorophyll
1511:{\displaystyle \rightleftharpoons }
1481:{\displaystyle \rightleftharpoons }
1415:{\displaystyle \rightleftharpoons }
1264:{\displaystyle \rightleftharpoons }
1191:{\displaystyle \rightleftharpoons }
1160:by catalysing the overall reaction
1118:{\displaystyle \rightleftharpoons }
1075:{\displaystyle \rightleftharpoons }
1020:{\displaystyle \rightleftharpoons }
971:{\displaystyle \rightleftharpoons }
916:Reduction steps to chlorophyllide a
860:{\displaystyle \rightleftharpoons }
795:{\displaystyle \rightleftharpoons }
724:{\displaystyle \rightleftharpoons }
219:
2238:Anoxygenic Photosynthetic Bacteria
2011:10.1111/j.1432-1033.1980.tb06100.x
25:
1434:. The reactions are catalysed by
993:This is followed by the reaction
1998:European Journal of Biochemistry
1935:10.1111/j.1432-1033.1996.0085u.x
1922:European Journal of Biochemistry
1398:+ 2 reduced ferredoxin + ATP + H
1007:protochlorophyllide + NADPH + H
33:
1383:, which catalyses the reaction
1054:3,8-divinylprotochlorophyllide
352:(at 25 °C , 100 kPa).
1:
1105:+ 2 reduced ferredoxin + 2 H
1002:protochlorophyllide reductase
883:, which can obtain them from
674:which catalyzes the reaction
1540:geranylgeranyl pyrophosphate
1436:chlorophyllide a 3-hydratase
889:Ferredoxin—NADP(+) reductase
618:) and bacteria (for example
93:: Chlorophyllide b
87:: Chlorophyllide a
834:gives the overall reaction
738:+ Mg-protoporphyrin IX + 2
457:, (R=H). In chlorophyllide
342:614.973 g/mol
2814:
1381:chlorophyllide a reductase
1101:3,8-divinylchlorophyllide
1082:3,8-divinylchlorophyllide
978:protochlorophyllide + NADP
928:reactions: one converts a
542:. The latter is the first
518:is created by the enzymes
506:Porphyrin § Synthesis
503:
2387:
2340:
1624:10.1007/s11120-006-9076-6
1050:but with the alternative
810:From porphyrin to chlorin
804:S-adenosyl-L-homocysteine
473:(R=H). In chlorophyllide
417:has been in the study of
346:
303:
283:
248:
77:
72:
50:
45:
32:
2527:Magnesium protoporphyrin
402:groups are converted to
2798:Photosynthetic pigments
2272:R. Caspi (2015-12-08).
2246:10.1007/0-306-47954-0_8
1745:R. Caspi (2007-07-18).
1712:Natural Product Reports
1612:Photosynthesis Research
1574:Natural Product Reports
1518:bacteriochlorophyllide
1372:Rhodobacter sphaeroides
1343:Bacteriochlorophyllide
1129:+ 2 oxidized ferredoxin
902:Rhodobacter sphaeroides
779:Mg-protoporphyrin IX +
546:intermediate common to
2204:10.3390/plants11070915
1512:
1482:
1416:
1366:Rhodobacter capsulatus
1356:
1265:
1231:
1192:
1119:
1076:
1021:
990:
972:
887:or, in the dark, from
861:
819:
796:
725:
649:
640:Insertion of magnesium
620:Rubrivivax gelatinosus
567:coproporphyrinogen III
462:
2627:Protoporphyrinogen IX
2103:10.1186/1471-2229-4-5
1884:10.3390/plants9091157
1513:
1483:
1417:
1377:trans stereochemistry
1342:
1266:
1251:+ phytyl diphosphate
1218:
1193:
1120:
1077:
1022:
985:
973:
862:
817:
797:
726:
647:
571:protoporphyrinogen IX
452:
2720:Bacteriochlorophyll
2699:Bacteriochlorophyll
2144:Biological Chemistry
1834:10.1104/pp.112.1.105
1502:
1472:
1406:
1359:Bacteriochlorophyll
1320:Bacteriochlorophylls
1255:
1235:Chlorophyll synthase
1182:
1134:From chlorophyllide
1109:
1066:
1039:, that uses reduced
1011:
962:
851:
786:
781:S-adenosylmethionine
715:
684:protoporphyrin IX +
603:Arabidopsis thaliana
540:uroporphyrinogen III
439:bacteriochlorophylls
411:chlorophyll synthase
398:respectively. Their
2733:Isobacteriochlorins
2568:Protochlorophyllide
2542:Zinc protoporphyrin
2156:10.1515/BC.2002.198
2055:10.1038/nature08950
2047:2010Natur.465..110M
1971:10.1021/bi00151a011
1773:Biochemical Journal
1671:1980Natur.285...17B
1546:bonds are reduced.
1283:with the 20-carbon
946:protochlorophyllide
897:anaerobic organisms
672:magnesium chelatase
536:hydroxymethylbilane
528:aminolevulinic acid
485:for chlorophyllide
29:
2613:Coproporphyrinogen
1785:10.1042/BJ20021394
1508:
1478:
1412:
1357:
1261:
1232:
1188:
1156:to chlorophyllide
1138:to chlorophyllide
1115:
1072:
1017:
991:
968:
857:
820:
792:
721:
650:
463:
415:chemical compounds
356:Infobox references
92:
86:
27:
2780:
2779:
2776:
2775:
2772:
2771:
2576:
2575:
2532:Protoporphyrin IX
2460:Adenosylcobalamin
2437:
2436:
2433:
2432:
2410:Phycoerythrobilin
2090:BMC Plant Biology
1965:(36): 8460–8464.
615:Triticum aestivum
609:Nicotiana tabacum
582:protoporphyrin IX
433:. Chlorophyllide
364:Chemical compound
362:
361:
147:Interactive image
90:
84:
16:(Redirected from
2805:
2746:Sirohydrochlorin
2712:Bacteriochlorins
2599:Uroporphyrinogen
2587:
2485:
2448:
2392:Phytochromobilin
2385:
2338:
2315:
2308:
2301:
2292:
2285:
2284:
2282:
2281:
2269:
2260:
2259:
2233:
2227:
2226:
2216:
2206:
2182:
2176:
2175:
2141:
2132:
2126:
2125:
2115:
2105:
2081:
2075:
2074:
2030:
2024:
2023:
2013:
1989:
1983:
1982:
1954:
1948:
1947:
1937:
1913:
1907:
1906:
1896:
1886:
1862:
1856:
1855:
1845:
1822:Plant Physiology
1813:
1807:
1806:
1796:
1764:
1758:
1757:
1755:
1754:
1742:
1736:
1735:
1724:10.1039/B002635M
1707:
1701:
1700:
1682:
1680:10.1038/285017a0
1650:
1644:
1643:
1607:
1598:
1597:
1586:10.1039/B110549N
1569:
1517:
1515:
1514:
1509:
1487:
1485:
1484:
1479:
1421:
1419:
1418:
1413:
1270:
1268:
1267:
1262:
1197:
1195:
1194:
1189:
1178:+ 2 NADPH + 2 H
1124:
1122:
1121:
1116:
1081:
1079:
1078:
1073:
1026:
1024:
1023:
1018:
977:
975:
974:
969:
866:
864:
863:
858:
801:
799:
798:
793:
748:
747:
746:
730:
728:
727:
722:
711:
709:
708:
694:
693:
692:
526:which transform
481:at position 13 (
421:biosynthesis in
311:Chemical formula
241:
233:
221:
207:
199:
178:
170:
149:
124:
116:
40:Chlorophyllide a
37:
30:
21:
18:Chlorophyllide b
2813:
2812:
2808:
2807:
2806:
2804:
2803:
2802:
2783:
2782:
2781:
2768:
2750:
2727:
2706:
2631:
2582:
2572:
2552:Phytoporphyrins
2546:
2489:Protoporphyrins
2474:
2470:Methylcobalamin
2429:
2425:Phycoviolobilin
2415:Phycocyanobilin
2396:
2374:
2355:Stercobilinogen
2333:
2325:
2319:
2289:
2288:
2279:
2277:
2271:
2270:
2263:
2256:
2235:
2234:
2230:
2184:
2183:
2179:
2150:(11): 1769–78.
2139:
2134:
2133:
2129:
2083:
2082:
2078:
2041:(7294): 110–4.
2032:
2031:
2027:
1991:
1990:
1986:
1956:
1955:
1951:
1915:
1914:
1910:
1864:
1863:
1859:
1815:
1814:
1810:
1766:
1765:
1761:
1752:
1750:
1744:
1743:
1739:
1709:
1708:
1704:
1665:(5759): 17–21.
1652:
1651:
1647:
1609:
1608:
1601:
1571:
1570:
1557:
1552:
1500:
1499:
1470:
1469:
1467:
1404:
1403:
1401:
1394:chlorophyllide
1337:
1317:
1253:
1252:
1247:chlorophyllide
1213:
1205:
1198:chlorophyllide
1180:
1179:
1177:
1170:chlorophyllide
1146:Chlorophyllide
1143:
1125:chlorophyllide
1107:
1106:
1064:
1063:
1061:
1027:chlorophyllide
1009:
1008:
960:
959:
918:
870:
849:
848:
847:
812:
784:
783:
760:
755:
745:
743:
742:
741:
739:
713:
712:
707:
704:
703:
702:
700:
691:
689:
688:
687:
685:
642:
598:
584:. Insertion of
559:
532:porphobilinogen
508:
502:
483:IUPAC numbering
471:carboxylic acid
465:Chlorophyllide
453:Chlorophyllide
447:
375:Chlorophyllide
368:Chlorophyllide
365:
358:
353:
331:
327:
323:
319:
313:
299:
296:
291:
290:
279:
276:
275:
272:
266:
265:
262:
256:
255:
244:
222:
210:
181:
152:
138:
127:
105:
96:
68:
41:
38:
28:Chlorophyllide
23:
22:
15:
12:
11:
5:
2811:
2809:
2801:
2800:
2795:
2785:
2784:
2778:
2777:
2774:
2773:
2770:
2769:
2767:
2766:
2760:
2758:
2752:
2751:
2749:
2748:
2743:
2737:
2735:
2729:
2728:
2726:
2725:
2716:
2714:
2708:
2707:
2705:
2704:
2696:
2678:
2660:
2645:Chlorophyllide
2641:
2639:
2633:
2632:
2630:
2629:
2624:
2610:
2595:
2593:
2591:Porphyrinogens
2584:
2578:
2577:
2574:
2573:
2571:
2570:
2565:
2556:
2554:
2548:
2547:
2545:
2544:
2539:
2534:
2529:
2524:
2493:
2491:
2482:
2476:
2475:
2473:
2472:
2467:
2465:Cyanocobalamin
2462:
2456:
2454:
2445:
2439:
2438:
2435:
2434:
2431:
2430:
2428:
2427:
2422:
2417:
2412:
2406:
2404:
2398:
2397:
2395:
2394:
2388:
2382:
2376:
2375:
2373:
2372:
2367:
2362:
2357:
2352:
2347:
2341:
2335:
2327:
2326:
2320:
2318:
2317:
2310:
2303:
2295:
2287:
2286:
2261:
2254:
2228:
2177:
2127:
2076:
2025:
2004:(1): 251–258.
1984:
1949:
1908:
1857:
1828:(1): 105–114.
1808:
1779:(2): 351–360.
1759:
1737:
1718:(6): 507–526.
1702:
1645:
1618:(2): 173–194.
1599:
1580:(6): 327–341.
1554:
1553:
1551:
1548:
1532:esterification
1524:
1523:
1507:
1492:
1477:
1465:
1456:) as follows:
1428:
1427:
1411:
1399:
1336:
1329:
1316:
1313:
1291:. Chlorophyll
1277:
1276:
1260:
1212:
1209:
1208:
1207:
1203:
1187:
1175:
1142:
1132:
1131:
1130:
1114:
1088:
1087:
1071:
1059:
1033:
1032:
1016:
980:
979:
967:
917:
914:
873:
872:
868:
856:
845:
811:
808:
807:
806:
791:
758:
754:
751:
750:
749:
744:
720:
705:
690:
641:
638:
597:
594:
557:
504:Main article:
501:
498:
446:
443:
409:by the enzyme
400:propionic acid
384:precursors of
363:
360:
359:
354:
350:standard state
347:
344:
343:
340:
334:
333:
329:
325:
321:
317:
314:
309:
306:
305:
301:
300:
298:
297:
294:
286:
285:
284:
281:
280:
278:
277:
273:
270:
269:
267:
263:
260:
259:
251:
250:
249:
246:
245:
243:
242:
234:
225:
223:
215:
212:
211:
209:
208:
200:
191:
189:
183:
182:
180:
179:
171:
162:
160:
154:
153:
151:
150:
141:
139:
132:
129:
128:
126:
125:
117:
108:
106:
101:
98:
97:
95:
94:
88:
82:
78:
75:
74:
70:
69:
54:
48:
47:
43:
42:
39:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2810:
2799:
2796:
2794:
2793:Tetrapyrroles
2791:
2790:
2788:
2765:
2764:Cofactor F430
2762:
2761:
2759:
2757:
2753:
2747:
2744:
2742:
2739:
2738:
2736:
2734:
2730:
2724:
2723:
2718:
2717:
2715:
2713:
2709:
2703:
2702:
2697:
2694:
2693:
2688:
2687:
2682:
2679:
2676:
2675:
2670:
2669:
2664:
2661:
2658:
2657:
2652:
2651:
2646:
2643:
2642:
2640:
2638:
2634:
2628:
2625:
2622:
2618:
2614:
2611:
2608:
2604:
2600:
2597:
2596:
2594:
2592:
2588:
2585:
2579:
2569:
2566:
2564:
2563:
2558:
2557:
2555:
2553:
2549:
2543:
2540:
2538:
2535:
2533:
2530:
2528:
2525:
2522:
2521:
2516:
2515:
2510:
2509:
2504:
2503:
2498:
2495:
2494:
2492:
2490:
2486:
2483:
2481:
2477:
2471:
2468:
2466:
2463:
2461:
2458:
2457:
2455:
2453:
2449:
2446:
2444:
2440:
2426:
2423:
2421:
2420:Phycourobilin
2418:
2416:
2413:
2411:
2408:
2407:
2405:
2403:
2399:
2393:
2390:
2389:
2386:
2383:
2381:
2377:
2371:
2368:
2366:
2363:
2361:
2358:
2356:
2353:
2351:
2348:
2346:
2343:
2342:
2339:
2336:
2332:
2328:
2324:
2323:tetrapyrroles
2316:
2311:
2309:
2304:
2302:
2297:
2296:
2293:
2275:
2268:
2266:
2262:
2257:
2255:0-7923-3681-X
2251:
2247:
2243:
2239:
2232:
2229:
2224:
2220:
2215:
2210:
2205:
2200:
2196:
2192:
2188:
2181:
2178:
2173:
2169:
2165:
2161:
2157:
2153:
2149:
2145:
2138:
2131:
2128:
2123:
2119:
2114:
2109:
2104:
2099:
2095:
2091:
2087:
2080:
2077:
2072:
2068:
2064:
2060:
2056:
2052:
2048:
2044:
2040:
2036:
2029:
2026:
2021:
2017:
2012:
2007:
2003:
1999:
1995:
1988:
1985:
1980:
1976:
1972:
1968:
1964:
1960:
1953:
1950:
1945:
1941:
1936:
1931:
1927:
1923:
1919:
1912:
1909:
1904:
1900:
1895:
1890:
1885:
1880:
1876:
1872:
1868:
1861:
1858:
1853:
1849:
1844:
1839:
1835:
1831:
1827:
1823:
1819:
1812:
1809:
1804:
1800:
1795:
1790:
1786:
1782:
1778:
1774:
1770:
1763:
1760:
1748:
1741:
1738:
1733:
1729:
1725:
1721:
1717:
1713:
1706:
1703:
1698:
1694:
1690:
1686:
1681:
1676:
1672:
1668:
1664:
1660:
1656:
1649:
1646:
1641:
1637:
1633:
1629:
1625:
1621:
1617:
1613:
1606:
1604:
1600:
1595:
1591:
1587:
1583:
1579:
1575:
1568:
1566:
1564:
1562:
1560:
1556:
1549:
1547:
1545:
1541:
1537:
1533:
1529:
1521:
1497:
1493:
1491:
1463:
1459:
1458:
1457:
1455:
1452:
1448:
1444:
1441:
1437:
1433:
1425:
1397:
1393:
1392:
1391:
1389:
1386:
1382:
1378:
1374:
1373:
1368:
1367:
1362:
1354:
1350:
1346:
1341:
1334:
1330:
1328:
1326:
1321:
1314:
1312:
1310:
1306:
1302:
1298:
1294:
1290:
1286:
1282:
1275:+ diphosphate
1274:
1250:
1246:
1245:
1244:
1243:
1240:
1236:
1230:
1226:
1222:
1217:
1210:
1201:
1173:
1169:
1168:
1167:
1166:
1163:
1159:
1155:
1151:
1149:
1141:
1137:
1133:
1128:
1104:
1100:
1099:
1098:
1096:
1093:
1085:
1057:
1056:
1055:
1053:
1049:
1046:
1042:
1038:
1030:
1006:
1005:
1004:
1003:
999:
996:
989:
984:
957:
956:
955:
954:
951:
947:
943:
939:
935:
931:
927:
923:
915:
913:
911:
908:
904:
903:
898:
894:
890:
886:
885:photosystem I
882:
878:
843:
842:
841:
840:
837:
833:
829:
825:
816:
809:
805:
782:
778:
777:
776:
775:
772:
768:
764:
752:
737:
733:
698:
683:
682:
681:
680:
677:
673:
670:
666:
662:
658:
655:
646:
639:
637:
635:
631:
627:
626:
625:Synechocystis
621:
617:
616:
611:
610:
605:
604:
595:
593:
591:
587:
583:
580:
577:to the fully
576:
572:
568:
564:
560:
553:
549:
545:
541:
537:
533:
529:
525:
521:
517:
513:
512:glutamic acid
507:
499:
497:
495:
492:
488:
484:
480:
476:
472:
468:
460:
456:
451:
444:
442:
440:
436:
432:
431:cyanobacteria
428:
424:
420:
416:
412:
408:
405:
401:
397:
396:
390:
389:
383:
379:
378:
372:
371:
357:
351:
345:
341:
339:
336:
335:
315:
312:
308:
307:
302:
293:
289:
282:
268:
258:
254:
247:
240:
235:
232:
227:
226:
224:
218:
214:
213:
206:
201:
198:
193:
192:
190:
188:
185:
184:
177:
172:
169:
164:
163:
161:
159:
156:
155:
148:
143:
142:
140:
136:
131:
130:
123:
118:
115:
110:
109:
107:
104:
100:
99:
89:
83:
80:
79:
76:
71:
66:
62:
58:
53:
49:
44:
36:
31:
19:
2721:
2700:
2691:
2685:
2673:
2667:
2655:
2649:
2644:
2561:
2560:Chlorophyll
2519:
2513:
2507:
2501:
2365:Urobilinogen
2278:. Retrieved
2237:
2231:
2194:
2190:
2180:
2147:
2143:
2130:
2093:
2089:
2079:
2038:
2034:
2028:
2001:
1997:
1987:
1962:
1959:Biochemistry
1958:
1952:
1928:(1): 85–92.
1925:
1921:
1911:
1874:
1870:
1860:
1825:
1821:
1811:
1776:
1772:
1762:
1751:. Retrieved
1740:
1715:
1711:
1705:
1662:
1658:
1648:
1615:
1611:
1577:
1573:
1535:
1527:
1525:
1519:
1495:
1489:
1461:
1431:
1429:
1423:
1395:
1370:
1364:
1360:
1358:
1353:acetyl group
1344:
1332:
1324:
1318:
1308:
1304:
1300:
1296:
1292:
1280:
1278:
1272:
1271:chlorophyll
1248:
1233:
1228:
1224:
1220:
1219:Chlorophyll
1199:
1171:
1157:
1153:
1147:
1144:
1139:
1135:
1126:
1102:
1089:
1083:
1034:
1028:
992:
987:
948:in reaction
921:
919:
900:
892:
874:
821:
756:
651:
623:
619:
613:
607:
601:
599:
524:cosynthetase
516:tetrapyrrole
509:
486:
479:methyl group
474:
466:
464:
458:
454:
434:
394:
393:chlorophyll
387:
386:chlorophyll
382:biosynthetic
376:
374:
369:
367:
366:
73:Identifiers
64:
60:
56:
55:Magnesium (3
2663:Chlorophyll
2402:Phycobilins
2380:Phytobilins
2360:Stercobilin
1877:(9): 1157.
1349:vinyl group
938:aromaticity
934:ethyl group
930:vinyl group
924:. Both are
767:methylation
657:coordinated
573:, which is
544:macrocyclic
419:chlorophyll
304:Properties
176:CHEBI:38209
168:CHEBI:16900
2787:Categories
2681:Pheophytin
2583:porphyrins
2537:Pterobilin
2480:Porphyrins
2452:Corrinoids
2443:Macrocycle
2350:Biliverdin
2280:2020-06-04
2197:(7): 915.
1753:2020-06-04
1550:References
1530:ready for
1522:+ NADH + H
1206:O + 2 NADP
1041:ferredoxin
881:ferredoxin
839:1.14.13.81
556:cofactor F
445:Structures
338:Molar mass
187:ChemSpider
133:3D model (
122:14428-12-7
114:14897-06-4
103:CAS Number
52:IUPAC name
2345:Bilirubin
2321:Types of
1506:⇌
1476:⇌
1454:1.1.1.396
1443:4.2.1.165
1410:⇌
1285:diterpene
1259:⇌
1186:⇌
1150:oxygenase
1113:⇌
1070:⇌
1052:substrate
1015:⇌
966:⇌
926:reduction
910:1.21.98.3
895:gene. In
855:⇌
790:⇌
774:2.1.1.11
769:reaction
736:phosphate
719:⇌
663:called a
659:within a
590:magnesium
563:cobalamin
520:deaminase
81:Compounds
2756:Corphins
2741:Siroheme
2637:Chlorins
2370:Urobilin
2334:(Linear)
2223:35406896
2164:12530542
2122:15086960
2063:20400946
1903:32911631
1852:12226378
1803:12489983
1732:11152419
1640:23808539
1632:17370354
1594:12828371
1402:O + 2 H
1388:1.3.7.15
1287:alcohol
1242:2.5.1.62
1165:1.3.7.13
1095:1.3.7.13
998:1.3.1.33
953:1.3.1.75
899:such as
893:Xantha-l
824:cyclised
579:aromatic
575:oxidised
552:sirohaem
380:are the
239:15775275
236:b:
228:a:
205:34999243
202:b:
194:a:
173:b:
165:a:
144:a:
119:b:
111:a:
2581:Reduced
2331:Bilanes
2214:9003380
2172:3099209
2071:4427639
2043:Bibcode
2020:7439188
1979:1390630
1944:8706723
1894:7570240
1794:1223276
1697:9070849
1689:6769048
1667:Bibcode
1048:1.3.7.7
828:pyrrole
765:in the
679:6.6.1.1
665:chlorin
634:enzymes
469:, is a
332:
217:PubChem
2252:
2221:
2211:
2191:Plants
2170:
2162:
2120:
2113:406501
2110:
2069:
2061:
2035:Nature
2018:
1977:
1942:
1901:
1891:
1871:Plants
1850:
1843:157929
1840:
1801:
1791:
1730:
1695:
1687:
1659:Nature
1638:
1630:
1592:
1544:alkene
1498:+ NAD
1445:) and
1355:shown.
1289:phytol
1227:, and
1031:+ NADP
932:to an
877:barley
669:enzyme
661:ligand
491:formyl
477:, the
423:plants
407:esters
404:phytyl
288:SMILES
231:439664
197:388735
46:Names
2168:S2CID
2140:(PDF)
2096:: 5.
2067:S2CID
1693:S2CID
1636:S2CID
1331:BChl
1202:+ 3 H
1174:+ 2 O
630:genes
494:group
427:algae
253:InChI
158:ChEBI
135:JSmol
2497:Heme
2250:ISBN
2219:PMID
2160:PMID
2118:PMID
2059:PMID
2016:PMID
1975:PMID
1940:PMID
1899:PMID
1848:PMID
1799:PMID
1728:PMID
1685:PMID
1628:PMID
1590:PMID
1369:and
1303:and
632:and
622:and
612:and
586:iron
569:and
548:haem
534:and
530:via
522:and
514:, a
429:and
391:and
373:and
2621:III
2607:III
2242:doi
2209:PMC
2199:doi
2152:doi
2148:383
2108:PMC
2098:doi
2051:doi
2039:465
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