KEGG ENZYME: 6.2.1.51

ENZYME: 6.2.1.51

Entry

EC 6.2.1.51                 Enzyme

Name

4-hydroxyphenylalkanoate adenylyltransferase FadD29;
fadD29 (gene name);
4-hydroxyphenylalkanoate adenylase

Class

Ligases;
Forming carbon-sulfur bonds;
Acid-thiol ligases

Sysname

4-hydroxyphenylalkanoate:holo-[(phenol)carboxyphthiodiolenone synthase] ligase

Reaction(IUBMB)

(1) ATP + 17-(4-hydroxyphenyl)heptadecanoate + holo-[(phenol)carboxyphthiodiolenone synthase] = AMP + diphosphate + 17-(4-hydroxyphenyl)heptadecanoyl-[(phenol)carboxyphthiodiolenone synthase] [RN:R11922];
(1a) ATP + 17-(4-hydroxyphenyl)heptadecanoate = diphosphate + 17-(4-hydroxyphenyl)heptadecanoyl-adenylate [RN:R11537];
(1b) 17-(4-hydroxyphenyl)heptadecanoyl-adenylate + holo-[(phenol)carboxyphthiodiolenone synthase] = AMP + 17-(4-hydroxyphenyl)heptadecanoyl-[(phenol)carboxyphthiodiolenone synthase] [RN:R11923];
(2) ATP + 19-(4-hydroxyphenyl)nonadecanoate + holo-[(phenol)carboxyphthiodiolenone synthase] = AMP + diphosphate + 19-(4-hydroxyphenyl)nonadecanoyl-[(phenol)carboxyphthiodiolenone synthase] [RN:R11924];
(2a) ATP + 19-(4-hydroxyphenyl)nonadecanoate = diphosphate + 19-(4-hydroxyphenyl)nonadecanoyl-adenylate [RN:R11538];
(2b) 19-(4-hydroxyphenyl)nonadecanoyl-adenylate + holo-[(phenol)carboxyphthiodiolenone synthase] = AMP + 19-(4-hydroxyphenyl)nonadecanoyl-[(phenol)carboxyphthiodiolenone synthase] [RN:R11925]

Reaction(KEGG)

R11537 R11538 R11922 R11923 R11924 R11925

Substrate

ATP [CPD:C00002];
17-(4-hydroxyphenyl)heptadecanoate [CPD:C21446];
holo-[(phenol)carboxyphthiodiolenone synthase];
17-(4-hydroxyphenyl)heptadecanoyl-adenylate;
19-(4-hydroxyphenyl)nonadecanoate [CPD:C21448];
19-(4-hydroxyphenyl)nonadecanoyl-adenylate

Product

AMP [CPD:C00020];
diphosphate [CPD:C00013];
17-(4-hydroxyphenyl)heptadecanoyl-[(phenol)carboxyphthiodiolenone synthase];
17-(4-hydroxyphenyl)heptadecanoyl-adenylate;
19-(4-hydroxyphenyl)nonadecanoyl-[(phenol)carboxyphthiodiolenone synthase];
19-(4-hydroxyphenyl)nonadecanoyl-adenylate

Comment

The mycobacterial enzyme participates in the biosynthesis of phenolphthiocerols. Following the substrate's activation by adenylation, it is transferred to an acyl-carrier protein domain within the enzyme, from which it is transferred to the phenolphthiocerol/phthiocerol polyketide synthase.

History

EC 6.2.1.51 created 2016 as EC 2.7.7.94, transferred 2017 to EC 6.2.1.51

Orthology

K21059

4-hydroxyphenylalkanoate adenylyltransferase

Genes

LBK:	LVISKB_P3-0014

MTU:	Rv2950c(fadD29)

MTV:	RVBD_2950c

MTC:

MT3023

MRA:	MRA_2977(fadD29)

MTF:	TBFG_12964

MTB:	TBMG_01021

MTK:	TBSG_01029

MTZ:	TBXG_001011

MTG:	MRGA327_18135

MTE:	CCDC5079_2709

MTUR:

CFBS_3109(fadD29)

MTL:	CCDC5180_2673

MTO:	MTCTRI2_3008(fadD29)

MTD:	UDA_2950c(fadD29)

MTN:	ERDMAN_3232(fadD29)

MTJ:	J112_15790

MTUB:

MT7199_2985

MTUC:

J113_20540

MTUE:

J114_15755

MTX:	M943_15195

MTUH:

I917_20720

MTUL:

TBHG_02880

MTUT:

HKBT1_3096(fadD29)

MTUU:

HKBT2_3101(fadD29)

MTQ:	HKBS1_3103(fadD29)

MBO:	BQ2027_MB2974C(fadD29)

MBB:	BCG_2971c(fadD29)

MBT:	JTY_2966(fadD29)

MBM:	BCGMEX_2966c(fadD29)

MBK:	K60_030560

MBX:

BCGT_2786

MAF:	MAF_29550(fadD29)

MMIC:

RN08_3252

MCE:	MCAN_29701(fadD29)

MCQ:	BN44_60425(fadD)

MCV:	BN43_40657(fadD)

MCX:	BN42_40949(fadD)

MCZ:	BN45_51361(fadD)

MORY:

MO_003081(fadD29)

MLE:	ML0132(fadD29)

MLB:	MLBr00132(fadD29)

MUL:	MUL_2002(fadD29)

MMI:	MMAR_1759(fadD29)

MMAE:

MMARE11_16780(fadD29)

MLI:	MULP_01914(fadD29)

MPSE:

MPSD_40780(fadD29)

MSHO:

MSHO_54840(fadD29)

MKN:	MKAN_23930

MHAD:

B586_03295

MBAI:

MB901379_01574

MLJ:	MLAC_28890(fadD29)

MSHJ:

MSHI_07200(fadD29)

MOT:	LTS72_16060

MLM:	MLPF_0160(fadD29)

» show all

Reference

1 [PMID:20553505]

Authors

Simeone R, Leger M, Constant P, Malaga W, Marrakchi H, Daffe M, Guilhot C, Chalut C

Title

Delineation of the roles of FadD22, FadD26 and FadD29 in the biosynthesis of phthiocerol dimycocerosates and related compounds in Mycobacterium tuberculosis.

Journal

FEBS J 277:2715-25 (2010)
DOI:10.1111/j.1742-464X.2010.07688.x

Sequence

[mtu:Rv2950c]

Reference

2 [PMID:25561717]

Authors

Vergnolle O, Chavadi SS, Edupuganti UR, Mohandas P, Chan C, Zeng J, Kopylov M, Angelo NG, Warren JD, Soll CE, Quadri LE

Title

Biosynthesis of cell envelope-associated phenolic glycolipids in Mycobacterium marinum.

Journal

J Bacteriol 197:1040-50 (2015)
DOI:10.1128/JB.02546-14