KEGG   ENZYME: 2.3.1.329
Entry
EC 2.3.1.329                Enzyme                                 
Name
isonitrile lipopeptide synthase;
scoA (gene name);
mmaA (gene name)
Class
Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups
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)
R13508
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
MTURv0101(nrp)
MTVRVBD_0101
MTCMT0110
MRAMRA_0106(nrp2)
MTFTBFG_10102
MTBTBMG_00102
MTKTBSG_00102
MTZTBXG_000102
MTGMRGA327_00650
MTURCFBS_0107
MTLCCDC5180_0089
MTOMTCTRI2_0104(nrp)
MTDUDA_0101(nrp)
MTNERDMAN_0118(nrp)
MTJJ112_00560
MTUBMT7199_0103
MTUEJ114_00565
MTXM943_00565
MTULTBHG_00102
MTUTHKBT1_0107
MTUUHKBT2_0107
MTQHKBS1_0107
MBOBQ2027_MB0104(nrp)
MBBBCG_0134(nrp)
MBTJTY_0105(nrp)
MBMBCGMEX_0105(nrp)
MBKK60_001130
MBXBCGT_3896
MAFMAF_01020(nrp)
MMICRN08_0118
MCEMCAN_01041(nrp)
MCQBN44_10124(nrp)
MCVBN43_10119(nrp)
MCXBN42_10139(nrp)
MCZBN45_10117(nrp)
MORYMO_000110(nrp)
MLEML1996(nrp)
MLBMLBr01996(nrp)
MULMUL_4858
MMIMMAR_0256
MMAEMMARE11_02390
MLIMULP_00228
MPSEMPSD_53430(nrp)
MSHOMSHO_13030(nrp)
MYVG155_20070
MHADB586_11355
MSHGMSG_03156(nrp_3)
MLWMJO58_18035
MPAGC0J29_01620
MGORH0P51_07715
MBAIMB901379_00190(ppsC_1)
MSPGF6B93_01090
MLMMLPF_3231
MWUPT015_11545
MFTXA26_40980
MFXMFAL_24270(nrp)
MIJMINS_08820(nrp)
MALVMALV_54170(nrp)
MHEVMHEL_38370(nrp)
MSARMSAR_36880(nrp)
MAUBMAUB_23270(nrp)
MPHUMPHO_47220(nrp)
MMUCC1S78_023645
MBOKMBOE_32820(nrp)
MFGK6L26_11660
MBRML2Z93_003588
MSENK3U95_09875
MABMAB_0663
MMVMYCMA_0349
MABBMASS_0634
MABLMMASJCM_0653
MCHEBB28_03165
MIZBAB75_03955
MSTEMSTE_00618
MSAOMYCSP_02855
MSALDSM43276_00574(dhbF_2)
MMINMMIN_13090(nrp)
MHERK3U94_21335
MVMMJO54_21230
SMASAVERM_603(nrps6)
SGBWQO_03755
SGMGCM10017557_04900
SGEDWG14_02625(dhbF)
SBYH7H31_26475
STSUB7R87_01600
SBROGQF42_33770
SKGKJK29_00705
STRZOYE22_25760
STRWQHG49_01205
SABDN8I86_36225
STRVEZV63_29760
 ยป show all
Reference
1  [PMID:22451903]
  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
Proc Natl Acad Sci U S A 109:5681-6 (2012)
DOI:10.1073/pnas.1118680109
  Sequence
[mtu:Rv0101]
Reference
2  [PMID:28634299]
  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
Proc Natl Acad Sci U S A 114:7025-7030 (2017)
DOI:10.1073/pnas.1705016114
  Sequence
[mtu:Rv0101] [mmi:MMAR_0256] [ag:UYZ56980]
Other DBs
ExplorEnz - The Enzyme Database: 2.3.1.329
IUBMB Enzyme Nomenclature: 2.3.1.329
ExPASy - ENZYME nomenclature database: 2.3.1.329
BRENDA, the Enzyme Database: 2.3.1.329
LinkDB

DBGET integrated database retrieval system