Entry
Name
4-hydroxyphenylalkanoate adenylyltransferase FadD29;
fadD29 (gene name);
4-hydroxyphenylalkanoate adenylase
Class
Ligases;
Forming carbon-sulfur bonds;
Acid-thiol ligases
BRITE hierarchy
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)
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
MTO : MTCTRI2_3008(fadD29)
MBO : BQ2027_MB2974C(fadD29)
MBM : BCGMEX_2966c(fadD29)
MMAE : MMARE11_16780(fadD29)
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Taxonomy
Reference
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
Sequence
Reference
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
Sequence
Other DBs
ExplorEnz - The Enzyme Database: 6.2.1.51
ExPASy - ENZYME nomenclature database: 6.2.1.51
LinkDB
All DBs