KEGG ENZYME: 1.1.1.364

ENZYME: 1.1.1.364

Entry

EC 1.1.1.364                Enzyme

Name

dTDP-4-dehydro-6-deoxy-alpha-D-gulose 4-ketoreductase;
dTDP-4-dehydro-6-deoxygulose reductase;
tylD (gene name);
gerKI (gene name);
chmD (gene name);
mydI (gene name)

Class

Oxidoreductases;
Acting on the CH-OH group of donors;
With NAD+ or NADP+ as acceptor

Sysname

dTDP-6-deoxy-alpha-D-allose:NAD(P)+ oxidoreductase

Reaction(IUBMB)

dTDP-6-deoxy-alpha-D-allose + NAD(P)+ = dTDP-4-dehydro-6-deoxy-alpha-D-gulose + NAD(P)H + H+ [RN:R06438 R10573]

Reaction(KEGG)

R06438 R10573

Substrate

dTDP-6-deoxy-alpha-D-allose [CPD:C11912];
NAD+ [CPD:C00003];
NADP+ [CPD:C00006]

Product

dTDP-4-dehydro-6-deoxy-alpha-D-gulose [CPD:C11926];
NADH [CPD:C00004];
NADPH [CPD:C00005];
H+ [CPD:C00080]

Comment

The enzyme forms an activated deoxy-alpha-D-allose, which is converted to mycinose after attachment to the aglycones of several macrolide antibiotics, including tylosin, chalcomycin, dihydrochalcomycin, and mycinamicin II.

History

EC 1.1.1.364 created 2013

Pathway

ec00523

Polyketide sugar unit biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K13313

dTDP-4-dehydro-6-deoxy-alpha-D-gulose 4-ketoreductase

Genes

PQI:	KH389_01255

FAP:	GR316_01820

TMK:	QGN29_03040

STRM:

M444_29920

SCAL:

I6J39_29640

SGK:	PET44_28340

AMI:

Amir_4843

NHY:	JQS43_06885

RLO:	GQ464_012990

Reference

1 [PMID:10510490]

Authors

Bate N, Cundliffe E

Title

The mycinose-biosynthetic genes of Streptomyces fradiae, producer of tylosin.

Journal

J Ind Microbiol Biotechnol 23:118-122 (1999)
DOI:10.1038/sj.jim.2900707

Sequence

[ag:AAD12165]

Reference

2 [PMID:12583909]

Authors

Anzai Y, Saito N, Tanaka M, Kinoshita K, Koyama Y, Kato F

Title

Organization of the biosynthetic gene cluster for the polyketide macrolide mycinamicin in Micromonospora griseorubida.

Journal

FEMS Microbiol Lett 218:135-41 (2003)
DOI:10.1111/j.1574-6968.2003.tb11509.x

Sequence

[ag:BAC57025]

Reference

3 [PMID:17053005]

Authors

Thuy TT, Liou K, Oh TJ, Kim DH, Nam DH, Yoo JC, Sohng JK

Title

Biosynthesis of dTDP-6-deoxy-beta-D-allose, biochemical characterization of dTDP-4-keto-6-deoxyglucose reductase (GerKI) from Streptomyces sp. KCTC 0041BP.

Journal

Glycobiology 17:119-26 (2007)
DOI:10.1093/glycob/cwl060

Sequence

[ag:ABB52541]

Reference

4 [PMID:23116432]

Authors

Kubiak RL, Phillips RK, Zmudka MW, Ahn MR, Maka EM, Pyeatt GL, Roggensack SJ, Holden HM

Title

Structural and functional studies on a 3'-epimerase involved in the biosynthesis of dTDP-6-deoxy-D-allose.

Journal

Biochemistry 51:9375-83 (2012)
DOI:10.1021/bi3012737