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- Name help_outline 71-hydroxychlorophyllide a Identifier CHEBI:83357 Charge -2 Formula C35H32MgN4O6 InChIKeyhelp_outline SLCXPQHXALJFPR-XXRBRTKDSA-K SMILEShelp_outline CCC1=C(CO)C2=[N+]3C1=Cc1c(C)c4C(=O)[C-](C(=O)OC)C5=C6[C@@H](CCC([O-])=O)[C@H](C)C7=[N+]6[Mg--]3(n1c45)n1c(=C7)c(C)c(C=C)c1=C2 2D coordinates Mol file for the small molecule Search links Involved in 5 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline NAD+ Identifier CHEBI:57540 (Beilstein: 3868403) help_outline Charge -1 Formula C21H26N7O14P2 InChIKeyhelp_outline BAWFJGJZGIEFAR-NNYOXOHSSA-M SMILEShelp_outline NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,142 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline chlorophyllide b Identifier CHEBI:83356 Charge -2 Formula C35H30MgN4O6 InChIKeyhelp_outline WSVKRUWOLPKKOO-XXRBRTKDSA-K SMILEShelp_outline CCC1=C(C=O)C2=[N+]3C1=Cc1c(C)c4C(=O)[C-](C(=O)OC)C5=C6[C@@H](CCC([O-])=O)[C@H](C)C7=[N+]6[Mg--]3(n1c45)n1c(=C7)c(C)c(C=C)c1=C2 2D coordinates Mol file for the small molecule Search links Involved in 4 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline NADH Identifier CHEBI:57945 (Beilstein: 3869564) help_outline Charge -2 Formula C21H27N7O14P2 InChIKeyhelp_outline BOPGDPNILDQYTO-NNYOXOHSSA-L SMILEShelp_outline NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,073 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:24768 | RHEA:24769 | RHEA:24770 | RHEA:24771 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Substrate specificity of chlorophyll(ide) b reductase in etioplasts of barley (Hordeum vulgare L.).
Scheumann V., Ito H., Tanaka A., Schoch S., Rudiger W.
Enzyme activity of chlorophyll(ide) b reductase is present in etioplasts. Recently the conversion of chlorophyllide b to chlorophyll a via 7(1)-hydroxychlorophyll a was demonstrated in barley etioplasts. We used zinc pheophorbide b for a detailed investigation of the reduction of the 7-formyl grou ... >> More
Enzyme activity of chlorophyll(ide) b reductase is present in etioplasts. Recently the conversion of chlorophyllide b to chlorophyll a via 7(1)-hydroxychlorophyll a was demonstrated in barley etioplasts. We used zinc pheophorbide b for a detailed investigation of the reduction of the 7-formyl group to the 7(1)-hydroxy compound in intact barley etioplasts. The reaction proceeded likewise before esterification and after esterification with phytyl diphosphate. The metal-free pheophorbide b, that is not accepted by chlorophyll synthase for esterification, is reduced to 7(1)-hydroxypheophorbide a to a small extent. The zinc (13(2)S)-pheophorbide b is at least equally well accepted for reduction as the epimer with the 13(2)R configuration of natural chlorophyll b. The reaction requires NADPH or NADH, although the latter is less effective. ATP is not required for the first step to the 7(1)-hydroxy compound. The significance of chlorophyll b reduction for acclimation from shade to sun leaves and for chlorophyll degradation is discussed. << Less
Eur J Biochem 242:163-170(1996) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.
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Chlorophyll a formation in the chlorophyll b reductase reaction requires reduced ferredoxin.
Scheumann V., Schoch S., Rudiger W.
The reduction of chlorophyllide b and its analogue zinc pheophorbide b in etioplasts of barley (Hordeum vulgare L.) was investigated in detail. In intact etioplasts, the reduction proceeds to chlorophyllide a and zinc pheophorbide a or, if incubated together with phytyldiphosphate, to chlorophyll ... >> More
The reduction of chlorophyllide b and its analogue zinc pheophorbide b in etioplasts of barley (Hordeum vulgare L.) was investigated in detail. In intact etioplasts, the reduction proceeds to chlorophyllide a and zinc pheophorbide a or, if incubated together with phytyldiphosphate, to chlorophyll a and zinc pheophytin a, respectively. In lysed etioplasts supplied with NADPH, the reduction stops at the intermediate step of 7(1)-OH-chlorophyll(ide) and Zn-7(1)-OH-pheophorbide or Zn-7(1)-OH-pheophytin. However, the final reduction is achieved when reduced ferredoxin is added to the lysed etioplasts, suggesting that ferredoxin is the natural cofactor for reduction of chlorophyll b to chlorophyll a. The reduction to chlorophyll a requires ATP in intact etioplasts but not in lysed etioplasts when reduced ferredoxin is supplied. The role of ATP and the significance of two cofactors for the two steps of reduction are discussed. << Less
J Biol Chem 273:35102-35108(1998) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.
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Conversion of chlorophyll b to chlorophyll a via 7-hydroxymethyl chlorophyll.
Ito H., Ohtsuka T., Tanaka A.
Chlorophyll b is synthesized from chlorophyll a by the oxidation of the methyl group on the ring B of the tetrapyrrole ring to the formyl group. Previously, we reported that chlorophyllide b could be converted to chlorophyll a in isolated cucumber etioplasts indicating the conversion of chlorophyl ... >> More
Chlorophyll b is synthesized from chlorophyll a by the oxidation of the methyl group on the ring B of the tetrapyrrole ring to the formyl group. Previously, we reported that chlorophyllide b could be converted to chlorophyll a in isolated cucumber etioplasts indicating the conversion of chlorophyll b to chlorophyll a. To identify the intermediate molecule, we used barley etioplasts instead of cucumber. Chlorophyll a and an additional pigment were found after incubation of chlorophyllide b with isolated barley etioplasts. The pigment has the same retention time and absorption spectrum as 7-hydroxymethyl chlorophyll, which has the hydroxymethyl group on ring B instead of the formyl group of chlorophyll b. Authentic 7-hydroxymethyl chlorophyll was prepared by reduction of chlorophyll b by NaBH4. Chlorophyll a accumulated during the incubation of 7-hydroxymethyl chlorophyllide with etioplasts. These findings indicate that chlorophyll b is converted to chlorophyll a via 7-hydroxymethyl chlorophyll. Chlorophyll b and 7-hydroxymethyl chlorophyll accumulated within a short period of incubation of chlorophyllide b with etioplasts. However, chlorophyll a accumulated with a concomitant decrease of chlorophyll b and 7-hydroxymethyl chlorophyll. These observations also suggest that chlorophyll b is converted to 7-hydroxymethyl chlorophyll and then to chlorophyll a. Both steps required ATP. << Less
J Biol Chem 271:1475-1479(1996) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.