KEGG ENZYME: 1.14.11.78

ENZYME: 1.14.11.78

Entry

EC 1.14.11.78               Enzyme

Name

(R)-3-[(carboxymethyl)amino]fatty acid dioxygenase/decarboxylase;
scoE (gene name);
mmaE (gene name);
Rv0097 (locus name)

Class

Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With 2-oxoglutarate as one donor, and incorporation of one atom of oxygen into each donor

Sysname

(3R)-3-[(carboxylmethyl)amino]fatty acid,2-oxoglutarate:oxygen oxidoreductase (isonitrile-forming)

Reaction(IUBMB)

a (3R)-3-[(carboxylmethyl)amino]fatty acid + 2 2-oxoglutarate + 2 O2 = a (3R)-3-isocyanyl-fatty acid + 2 succinate + 3 CO2 + 2 H2O (overall reaction) [RN:R13014];
(1a) a (3R)-3-[(carboxylmethyl)amino]fatty acid + 2-oxoglutarate + O2 = a (3R)-3-{[carboxy(hydroxy)methyl]amino}fatty acid + succinate + CO2 [RN:R13012];
(1b) a (3R)-3-{[carboxy(hydroxy)methyl]amino}fatty acid + 2-oxoglutarate + O2 = a (3R)-3-isocyanyl-fatty acid + succinate + 2 CO2 + 2 H2O [RN:R13013]

Reaction(KEGG)

R13012 R13013 R13014

Substrate

(3R)-3-[(carboxylmethyl)amino]fatty acid [CPD:C22516];
2-oxoglutarate [CPD:C00026];
O2 [CPD:C00007];
(3R)-3-{[carboxy(hydroxy)methyl]amino}fatty acid [CPD:C22517]

Product

(3R)-3-isocyanyl-fatty acid [CPD:C22518];
succinate [CPD:C00042];
CO2 [CPD:C00011];
H2O [CPD:C00001];
(3R)-3-{[carboxy(hydroxy)methyl]amino}fatty acid [CPD:C22517]

Comment

Requires Fe(II). The enzyme, found in actinobacterial species, participates in the biosynthesis of isonitrile-containing lipopeptides. The reaction comprises two catalytic cycles, each consuming an oxygen molecule and a 2-oxoglutarate molecule. In the first cycle the substrate is hydroxylated, while in the second cycle the enzyme catalyses a decarboxylation/oxidation reaction that produces an isonitrile group.

History

EC 1.14.11.78 created 2022

Orthology

K25987

(R)-3-[(carboxymethyl)amino]fatty acid dioxygenase/decarboxylase

Genes

HNA:	Hneap_0955

CHRO:

CXB49_14790

BCAI:

K788_0006366

MTU:

Rv0097

MTV:

RVBD_0097

MTC:

MT0106

MRA:

MRA_0101

MTF:	TBFG_10098

MTB:	TBMG_00098

MTK:	TBSG_00098

MTZ:	TBXG_000098

MTG:	MRGA327_00625

MTI:	MRGA423_00625

MTE:	CCDC5079_0085

MTUR:

CFBS_0103

MTL:	CCDC5180_0086

MTO:	MTCTRI2_0100

MTD:

UDA_0097

MTN:	ERDMAN_0114

MTJ:	J112_00540

MTUB:

MT7199_0099

MTUC:

J113_00660

MTUE:

J114_00545

MTX:	M943_00545

MTUL:

TBHG_00098

MTUT:

HKBT1_0103

MTUU:

HKBT2_0103

MTQ:	HKBS1_0103

MBO:	BQ2027_MB0100

MBB:

BCG_0130

MBT:

JTY_0101

MBM:	BCGMEX_0101

MBK:	K60_001090

MBX:

BCGT_3892

MAF:

MAF_00980

MMIC:

RN08_0114

MCE:	MCAN_01001

MCQ:	BN44_10120

MCV:	BN43_10115

MCX:	BN42_10135

MCZ:	BN45_10113

MORY:

MO_000106

MLE:

ML1992

MLB:

MLBr01992

MUL:

MUL_4854

MMI:

MMAR_0260

MMAE:

MMARE11_02430

MLI:	MULP_00232

MSHO:

MSHO_13070

MYV:	G155_20090

MHAD:

B586_11335

MSHG:

MSG_00073 MSG_03152

MLW:	MJO58_18015 MJO58_18060

MPAG:

C0J29_01600

MGOR:

H0P51_07735

MBAI:

MB901379_00194(tauD_1)

MSPG:

F6B93_01070

MLM:

MLPF_3235

MKY:	IWGMT90018_16040

MWU:	PT015_11525

MFT:	XA26_41020

MFX:	MFAL_24230

MIJ:	MINS_08860

MALV:

MALV_54130

MHEV:

MHEL_38330 MHEL_38420

MSAR:

MSAR_36840 MSAR_36930

MAUB:

MAUB_23310 MAUB_23350

MPHU:

MPHO_47180

MMUC:

C1S78_023665

MBOK:

MBOE_32780

MFG:	K6L26_11640

MBRM:

L2Z93_003584

MSEN:

K3U95_09855

MAB:

MAB_0659

MMV:	MYCMA_0346

MABB:

MASS_0630

MABL:

MMASJCM_0649

MCHE:

BB28_03145

MIZ:	BAB75_03935

MSTE:

MSTE_00614

MSAO:

MYCSP_02835

MSAL:

DSM43276_00570(tfdA)

MMIN:

MMIN_13050

MHER:

K3U94_21315

MVM:	MJO54_21210

CPRE:

Csp1_27300

CHEI:

CHEID_00375(tauD)

CFEU:

CFELI_06600(tauD)

CHAN:

CHAN_10740(tauD)

NBR:	O3I_034365

NTP:	CRH09_21095

NOZ:	DMB37_13095

NAH:	F5544_19260

NIE:	KV110_33060

NYU:	D7D52_08840

GAM:	GII34_17735

GPD:	GII33_17145

SMA:	SAVERM_607

SGB:

WQO_03775

SBH:

SBI_00519

SGM:	GCM10017557_04940

SNW:	BBN63_00220

SGE:	DWG14_02621

SBY:	H7H31_00885 H7H31_26455

STSU:

B7R87_01580

SBRO:

GQF42_33750

SHAR:

HUT13_09610

SCAE:

IHE65_04260

SKG:	KJK29_00725

STTN:

BSL84_14055

STRZ:

OYE22_00980 OYE22_25740

AMYC:

CU254_21790

KAL:

KALB_7700

ACTU:

Actkin_01836(tauD)

CCAZ:

COUCH_33510

NED:	HUN01_03905

HBQ:	QI031_30705

» show all

Reference

1 [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:Rv0097] [mmi:MMAR_0260]

Reference

2 [PMID:29906336]

Authors

Harris NC, Born DA, Cai W, Huang Y, Martin J, Khalaf R, Drennan CL, Zhang W.

Title

Isonitrile Formation by a Non-Heme Iron(II)-Dependent Oxidase/Decarboxylase.

Journal

Angew Chem Int Ed Engl 57:9707-9710 (2018)
DOI:10.1002/anie.201804307

Reference

3 [PMID:33361191]

Authors

Jonnalagadda R, Del Rio Flores A, Cai W, Mehmood R, Narayanamoorthy M, Ren C, Zaragoza JPT, Kulik HJ, Zhang W, Drennan CL.

Title

Biochemical and crystallographic investigations into isonitrile formation by a nonheme iron-dependent oxidase/decarboxylase.

Journal

J Biol Chem 296:100231 (2021)
DOI:10.1074/jbc.RA120.015932

Other DBs

ExplorEnz - The Enzyme Database:

1.14.11.78

IUBMB Enzyme Nomenclature:

1.14.11.78

ExPASy - ENZYME nomenclature database:

1.14.11.78

BRENDA, the Enzyme Database:

1.14.11.78

All links

Chemical substance (8)   
   KEGG COMPOUND (8)   
Chemical reaction (3)   
   KEGG REACTION (3)   
Gene (125)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (124)   
Protein sequence (10)   
   UniProt (5)   
   SWISS-PROT (5)   
Protein domain (3)   
   InterPro (3)   
All databases (149)   

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