KEGG   ORTHOLOGY: K21312
Entry
K21312                      KO                                     
Symbol
bciD
Name
bacteriochlorophyllide c C-7(1)-hydroxylase [EC:1.17.98.2]
Pathway
map00860  Porphyrin metabolism
map01110  Biosynthesis of secondary metabolites
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09108 Metabolism of cofactors and vitamins
   00860 Porphyrin metabolism
    K21312  bciD; bacteriochlorophyllide c C-7(1)-hydroxylase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.17  Acting on CH or CH2 groups
   1.17.98  With other, known, physiological acceptors
    1.17.98.2  bacteriochlorophyllide c C-71-hydroxylase
     K21312  bciD; bacteriochlorophyllide c C-7(1)-hydroxylase
Other DBs
RN: R11710
COG: COG0502
Genes
CLZ: BIU88_11010
CPH: Cpha266_0196
CPB: Cphamn1_0270
PPH: Ppha_2747
PROC: Ptc2401_00216
Reference
  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
LinkDB

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 metabolism
ec01110  Biosynthesis of secondary metabolites
Orthology
K21312  bacteriochlorophyllide c C-7(1)-hydroxylase
Genes
CLZBIU88_11010
CPHCpha266_0196
CPBCphamn1_0270
PPHPpha_2747
PROCPtc2401_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
LinkDB

KEGG   REACTION: R11710
Entry
R11710                      Reaction                               
Name
bacteriochlorophyllide-c:S-adenosyl-L-methionine oxidoreductase (C-7(1)-hydroxylating)
Definition
2 S-Adenosyl-L-methionine + Bacteriochlorophyllide c + H2O <=> Bacteriochlorophyllide e + 2 5'-Deoxyadenosine + 2 L-Methionine
Equation
2 C00019 + C18161 + C00001 <=> C21582 + 2 C05198 + 2 C00073
Comment
three-step reaction (see R11484+R10437+R11709)
Reaction class
RC00769  C18161_C21582
Enzyme
Pathway
rn00860  Porphyrin metabolism
rn01110  Biosynthesis of secondary metabolites
Orthology
K21312  bacteriochlorophyllide c C-7(1)-hydroxylase [EC:1.17.98.2]
Other DBs
RHEA: 52255
LinkDB

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