Entry
Name
isonitrile lipopeptide synthase;
scoA (gene name);
mmaA (gene name)
Class
Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups
BRITE hierarchy
Sysname
(3R)-3-isocyano-fatty acyl-[acyl-carrier protein]:L-lysyl-[L-lysyl-carrier protein] (3R)-3-isocyano-fatty acyltransferase (hydrolysing)
Reaction(IUBMB)
2 (3R)-3-isocyanobutanoyl-[acyl-carrier protein] + L-lysyl-[L-lysyl-carrier protein] + 2 NADPH = (3R)-N-[(2S)-1-hydroxy-6-[(3R)-3-isocyanobutanamido]hexan-2-yl]-3-isocyanobutanamide + [L-lysyl-carrier protein] + 2 [acyl-carrier protein] + 2 NADP+ [RN:
R13508 ]
Reaction(KEGG)
Substrate
(3R)-3-isocyanobutanoyl-[acyl-carrier protein] [CPD:
C23044 ];
L-lysyl-[L-lysyl-carrier protein] [CPD:
C23045 ];
NADPH [CPD:
C00005 ]
Product
(3R)-N-[(2S)-1-hydroxy-6-[(3R)-3-isocyanobutanamido]hexan-2-yl]-3-isocyanobutanamide [CPD:
C23046 ];
[L-lysyl-carrier protein] [CPD:
C23047 ];
[acyl-carrier protein] [CPD:
C00229 ];
NADP+ [CPD:
C00006 ]
Comment
The enzyme, found in some actinobacterial species, is a non-ribosomal peptide synthase (NRPS). Adenylation and thiolation domains of the enzyme activate a lysine residue and load it on the enzyme (this activity is described separately as EC
6.2.1.77 , L-lysine---[L-lysyl-carrier protein] ligase). A condensation domain catalyses the condensation of two isonitrile-containing moieties to both amino groups of the lysine, a rare activity in non-ribosomal peptide biosynthesis. A reductase domain catalyses a four-electron reduction, releasing the product from the NRPS with a terminal alcohol group.
History
EC 2.3.1.329 created 2025
Orthology
K28320 isonitrile lipopeptide synthase
K28321 isonitrile lipopeptide synthase / L-lysine---[L-lysyl-carrier protein] ligase
Genes
MBAI : MB901379_00190(ppsC_1)
MSAL : DSM43276_00574(dhbF_2)
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Taxonomy
Reference
Authors
Chhabra A, Haque AS, Pal RK, Goyal A, Rai R, Joshi S, Panjikar S, Pasha S, Sankaranarayanan R, Gokhale RS.
Title
Nonprocessive [2 + 2]e- off-loading reductase domains from mycobacterial nonribosomal peptide synthetases.
Journal
Sequence
Reference
Authors
Harris NC, Sato M, Herman NA, Twigg F, Cai W, Liu J, Zhu X, Downey J, Khalaf R, Martin J, Koshino H, Zhang W.
Title
Biosynthesis of isonitrile lipopeptides by conserved nonribosomal peptide synthetase gene clusters in Actinobacteria.
Journal
Sequence
Other DBs
ExPASy - ENZYME nomenclature database: 2.3.1.329
LinkDB
All DBs