KEGG ORTHOLOGY: K13330

ORTHOLOGY: K13330

Entry

K13330                      KO

Symbol

spnS

Name

dTDP-4-amino-2,3,4,6-tetradeoxy-D-glucose N,N-dimethyltransferase [EC:2.1.1.324]

Pathway

map00523

Polyketide sugar unit biosynthesis

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

map01250

Biosynthesis of nucleotide sugars

Module

M00802

dTDP-D-forosamine biosynthesis

Reaction

R08932

S-adenosyl-L-methionine:dTDP-4-amino-2,3,4,6-tetradeoxy-D-glucose N,N-dimethyltransferase

R11452

S-adenosyl-L-methionine:dTDP-4-amino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranose N-methyltransferase

R11453

S-adenosyl-L-methionine:dTDP-4-(methylamino)-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranose N-methyltransferase

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00523 Polyketide sugar unit biosynthesis
    K13330  spnS; dTDP-4-amino-2,3,4,6-tetradeoxy-D-glucose N,N-dimethyltransferase
Enzymes [BR:ko01000]
2. Transferases
  2.1  Transferring one-carbon groups
   2.1.1  Methyltransferases
    2.1.1.324  dTDP-4-amino-2,3,4,6-tetradeoxy-D-glucose N,N-dimethyltransferase
     K13330  spnS; dTDP-4-amino-2,3,4,6-tetradeoxy-D-glucose N,N-dimethyltransferase

Genes

SANL:

KZO11_24470

SVU:	B1H20_29845

SCAL:

APRE:

AMI:

CROS:

AG:	AAG23280(spnS)

Reference

PMID:18345667

Authors

Hong L, Zhao Z, Melancon CE 3rd, Zhang H, Liu HW

Title

In vitro characterization of the enzymes involved in TDP-D-forosamine biosynthesis in the spinosyn pathway of Saccharopolyspora spinosa.

Journal

J Am Chem Soc 130:4954-67 (2008)
DOI:10.1021/ja0771383

Reference

PMID:11358695

Authors

Waldron C, Matsushima P, Rosteck PR Jr, Broughton MC, Turner J, Madduri K, Crawford KP, Merlo DJ, Baltz RH

Title

Cloning and analysis of the spinosad biosynthetic gene cluster of Saccharopolyspora spinosa.

Journal

Chem Biol 8:487-99 (2001)
DOI:10.1016/S1074-5521(01)00029-1

Sequence

[ag:AAG23280]

LinkDB

ENZYME: 2.1.1.324

Entry

EC 2.1.1.324                Enzyme

Name

dTDP-4-amino-2,3,4,6-tetradeoxy-D-glucose N,N-dimethyltransferase;
SpnS;
TDP-4-amino-2,3,6-trideoxy-D-glucose N,N-dimethyltransferase

Class

Transferases;
Transferring one-carbon groups;
Methyltransferases

Sysname

S-adenosyl-L-methionine:dTDP-4-amino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranose N,N-dimethyltransferase

Reaction(IUBMB)

2 S-adenosyl-L-methionine + dTDP-4-amino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranose = 2 S-adenosyl-L-homocysteine + dTDP-alpha-D-forosamine (overall reaction) [RN:R08932];
(1a) S-adenosyl-L-methionine + dTDP-4-amino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranose = S-adenosyl-L-homocysteine + dTDP-4-(methylamino)-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranose [RN:R11452];
(1b) S-adenosyl-L-methionine + dTDP-4-(methylamino)-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranose = S-adenosyl-L-homocysteine + dTDP-alpha-D-forosamine [RN:R11453]

Reaction(KEGG)

R08932 R11452 R11453

Substrate

S-adenosyl-L-methionine [CPD:C00019];
dTDP-4-amino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranose [CPD:C18033];
dTDP-4-(methylamino)-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranose [CPD:C21395]

Product

S-adenosyl-L-homocysteine [CPD:C00021];
dTDP-alpha-D-forosamine [CPD:C18034];
dTDP-4-(methylamino)-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranose [CPD:C21395]

Comment

The enzyme was isolated from the bacterium Saccharopolyspora spinosa, where it is involved in the biosynthesis of spinosyn A, an active ingredient of several commercial insecticides.

History

EC 2.1.1.324 created 2016

Pathway

ec00523

Polyketide sugar unit biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K13330

dTDP-4-amino-2,3,4,6-tetradeoxy-D-glucose N,N-dimethyltransferase

Genes

SANL:

KZO11_24470

SVU:	B1H20_29845

SCAL:

I6J39_29650

APRE:

CNX65_21845

AMI:

Amir_4362

CROS:

N8J89_26380

Reference

1 [PMID:18345667]

Authors

Hong L, Zhao Z, Melancon CE 3rd, Zhang H, Liu HW

Title

In vitro characterization of the enzymes involved in TDP-D-forosamine biosynthesis in the spinosyn pathway of Saccharopolyspora spinosa.

Journal

J Am Chem Soc 130:4954-67 (2008)
DOI:10.1021/ja0771383

Other DBs

ExplorEnz - The Enzyme Database:

2.1.1.324

IUBMB Enzyme Nomenclature:

2.1.1.324

ExPASy - ENZYME nomenclature database:

2.1.1.324

BRENDA, the Enzyme Database:

2.1.1.324

LinkDB

REACTION: R08932

Entry

R08932                      Reaction

Name

S-adenosyl-L-methionine:dTDP-4-amino-2,3,4,6-tetradeoxy-D-glucose N,N-dimethyltransferase

Definition

dTDP-4-amino-2,3,4,6-tetradeoxy-D-glucose + 2 S-Adenosyl-L-methionine <=> dTDP-D-forosamine + 2 S-Adenosyl-L-homocysteine

Equation

C18033 + 2 C00019 <=> C18034 + 2 C00021

Comment

two-step reaction (see R11452+R11453)

Reaction class

RC00003

C00019_C00021

RC01515

C18033_C18034

Enzyme

2.1.1.324

Pathway

rn00523

Polyketide sugar unit biosynthesis

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

rn01250

Biosynthesis of nucleotide sugars

Module

M00802

dTDP-D-forosamine biosynthesis

Brite

Enzymatic reactions [BR:br08201]
2. Transferase reactions
  2.1  Transferring one-carbon groups
   2.1.1  Methyltransferases
    2.1.1.324
     R08932  dTDP-4-amino-2,3,4,6-tetradeoxy-D-glucose + 2 S-Adenosyl-L-methionine <=> dTDP-D-forosamine + 2 S-Adenosyl-L-homocysteine

Orthology

K13330

dTDP-4-amino-2,3,4,6-tetradeoxy-D-glucose N,N-dimethyltransferase [EC:2.1.1.324]

Other DBs

RHEA:

49151

LinkDB

DBGET integrated database retrieval system