KEGG   ENZYME: 1.17.98.2
Entry
EC 1.17.98.2                Enzyme                                 

Name
bacteriochlorophyllide c C-71-hydroxylase;
bciD (gene name)
Class
Oxidoreductases;
Acting on CH or CH2 groups;
With other, known, physiological acceptors
Sysname
bacteriochlorophyllide-c:S-adenosyl-L-methionine oxidoreductase (C-71-hydroxylating)
Reaction(IUBMB)
2 S-adenosyl-L-methionine + a bacteriochlorophyllide c + H2O = a bacteriochlorophyllide e + 2 5'-deoxyadenosine + 2 L-methionine (overall reaction) [RN:R11710];
(1a) S-adenosyl-L-methionine + a bacteriochlorophyllide c + H2O = a 7-(hydroxymethyl)bacteriochlorophyllide c + 5'-deoxyadenosine + L-methionine [RN:R11484];
(1b) S-adenosyl-L-methionine + a 7-(hydroxymethyl)bacteriochlorophyllide c + H2O = a 7-(dihydroxymethyl)bacteriochlorophyllide c + 5'-deoxyadenosine + L-methionine [RN:R10437];
(1c) a 7-(dihydroxymethyl)bacteriochlorophyllide c = a bacteriochlorophyllide e + H2O (spontaneous) [RN:R11709]
Reaction(KEGG)
Substrate
S-adenosyl-L-methionine [CPD:C00019];
bacteriochlorophyllide c [CPD:C18161];
H2O [CPD:C00001];
7-(hydroxymethyl)bacteriochlorophyllide c [CPD:C21407];
7-(dihydroxymethyl)bacteriochlorophyllide c [CPD:C20650]
Product
bacteriochlorophyllide e [CPD:C21582];
5'-deoxyadenosine [CPD:C05198];
L-methionine [CPD:C00073];
7-(hydroxymethyl)bacteriochlorophyllide c [CPD:C21407];
7-(dihydroxymethyl)bacteriochlorophyllide c [CPD:C20650];
H2O [CPD:C00001]
Comment
The enzyme, found in green sulfur bacteria (Chlorobiaceae), is a radical S-adenosyl-L-methionine (AdoMet) enzyme and contains a [4Fe-4S] cluster. It catalyses two consecutive hydroxylation reactions of the C-7 methyl group of bacteriochlorophyllide c to form a geminal diol intermediate that spontaneously dehydrates to produce the formyl group of bacteriochlorophyllide e.
History
EC 1.17.98.2 created 2016, modified 2017
Pathway
ec00860  Porphyrin and chlorophyll metabolism
ec01110  Biosynthesis of secondary metabolites
Orthology
K21312  bacteriochlorophyllide c C-7(1)-hydroxylase
Genes
CLZ: BIU88_11010
CPH: Cpha266_0196
CPB: Cphamn1_0270
PPH: Ppha_2747
PROC: Ptc2401_00216
Reference
1  [PMID:23560066]
  Authors
Harada J, Mizoguchi T, Satoh S, Tsukatani Y, Yokono M, Noguchi M, Tanaka A, Tamiaki H
  Title
Specific gene bciD for C7-methyl oxidation in bacteriochlorophyll e biosynthesis of brown-colored green sulfur bacteria.
  Journal
PLoS One 8:e60026 (2013)
DOI:10.1371/journal.pone.0060026
  Sequence
Reference
2  [PMID:27994052]
  Authors
Thweatt JL, Ferlez BH, Golbeck JH, Bryant DA
  Title
BciD Is a Radical S-Adenosyl-l-methionine (SAM) Enzyme That Completes Bacteriochlorophyllide e Biosynthesis by Oxidizing a Methyl Group into a Formyl Group at C-7.
  Journal
J Biol Chem 292:1361-1373 (2017)
DOI:10.1074/jbc.M116.767665
Other DBs
ExplorEnz - The Enzyme Database: 1.17.98.2
IUBMB Enzyme Nomenclature: 1.17.98.2
ExPASy - ENZYME nomenclature database: 1.17.98.2
BRENDA, the Enzyme Database: 1.17.98.2

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