KEGG ORTHOLOGY: K14368

ORTHOLOGY: K14368

Entry

K14368                      KO

Symbol

eryCIII

Name

3-alpha-mycarosylerythronolide B desosaminyl transferase [EC:2.4.1.278]

Pathway

map00522

Biosynthesis of 12-, 14- and 16-membered macrolides

map01052

Type I polyketide structures

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

Module

M00774

Erythromycin biosynthesis, propanoyl-CoA + methylmalonyl-CoA => deoxyerythronolide B => erythromycin A/B

Reaction

R05531

dTDP-D-desosamine:3-O-mycarosylerythronolide-B 5-O-beta-D-desosaminyltransferase

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   01052 Type I polyketide structures
    K14368  eryCIII; 3-alpha-mycarosylerythronolide B desosaminyl transferase
   00522 Biosynthesis of 12-, 14- and 16-membered macrolides
    K14368  eryCIII; 3-alpha-mycarosylerythronolide B desosaminyl transferase
09180 Brite Hierarchies
  09181 Protein families: metabolism
   01008 Polyketide biosynthesis proteins
    K14368  eryCIII; 3-alpha-mycarosylerythronolide B desosaminyl transferase
Enzymes [BR:ko01000]
2. Transferases
  2.4  Glycosyltransferases
   2.4.1  Hexosyltransferases
    2.4.1.278  3-alpha-mycarosylerythronolide B desosaminyl transferase
     K14368  eryCIII; 3-alpha-mycarosylerythronolide B desosaminyl transferase
Polyketide biosynthesis proteins [BR:ko01008]
Polyketide tailoring proteins
  Glycosyltransferase
   K14368  eryCIII; 3-alpha-mycarosylerythronolide B desosaminyl transferase

Other DBs

COG:

COG1819

CAZy:

GT1

Genes

SANL:

KZO11_24460

SCYE:

R2B67_24645 R2B67_24660

SNR:	SNOUR_10095

SGF:	HEP81_07908

SCIR:

STRCI_006233

SLON:

LGI35_31705

SDRZ:

NEH16_32015

SKG:	KJK29_16100

KCH:	O1G21_27110

AER:	AERYTH_15900

NEX:	NE857_19565

SEN:	SACE_0726(eryCIII)

ACOR:

LCL61_12300

AEY:	CDG81_13160

AG:	AAG13921(megCIII)

» show all

Reference

PMID:9353926

Authors

Summers RG, Donadio S, Staver MJ, Wendt-Pienkowski E, Hutchinson CR, Katz L.

Title

Sequencing and mutagenesis of genes from the erythromycin biosynthetic gene cluster of Saccharopolyspora erythraea that are involved in L-mycarose and D-desosamine production.

Journal

Microbiology 143:3251-62 (1997)
DOI:10.1099/00221287-143-10-3251

Sequence

[sen:SACE_0726]

Reference

PMID:9563840

Authors

Salah-Bey K, Doumith M, Michel JM, Haydock S, Cortes J, Leadlay PF, Raynal MC

Title

Targeted gene inactivation for the elucidation of deoxysugar biosynthesis in the erythromycin producer Saccharopolyspora erythraea.

Journal

Mol Gen Genet 257:542-53 (1998)
DOI:10.1007/s004380050680

LinkDB

ENZYME: 2.4.1.278

Entry

EC 2.4.1.278                Enzyme

Name

3-alpha-mycarosylerythronolide B desosaminyl transferase;
EryCIII;
dTDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose:3-alpha-mycarosylerythronolide B 3-dimethylamino-4,6-dideoxy-alpha-D-glucosyltransferase

Class

Transferases;
Glycosyltransferases;
Hexosyltransferases

Sysname

dTDP-3-dimethylamino-3,4,6-trideoxy-alpha-D-glucopyranose:3-alpha-mycarosylerythronolide B 3-dimethylamino-3,4,6-trideoxy-beta-D-glucosyltransferase

Reaction(IUBMB)

dTDP-D-desosamine + 3-alpha-L-mycarosylerythronolide B = dTDP + erythromycin D [RN:R05531]

Reaction(KEGG)

R05531

Substrate

dTDP-D-desosamine [CPD:C11911];
3-alpha-L-mycarosylerythronolide B [CPD:C06630]

Product

dTDP [CPD:C00363];
erythromycin D [CPD:C06633]

Comment

The enzyme is involved in erythromycin biosynthesis.

History

EC 2.4.1.278 created 2012, modified 2014

Pathway

ec00522

Biosynthesis of 12-, 14- and 16-membered macrolides

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K14368

3-alpha-mycarosylerythronolide B desosaminyl transferase

Genes

SANL:

KZO11_24460

SCYE:

R2B67_24645 R2B67_24660

SNR:	SNOUR_10095

SGF:	HEP81_07908

SCIR:

STRCI_006233

SLON:

LGI35_31705

SDRZ:

NEH16_32015

SKG:	KJK29_16100

KCH:	O1G21_27110

AER:	AERYTH_15900

NEX:	NE857_19565

SEN:	SACE_0726(eryCIII)

ACOR:

LCL61_12300

AEY:	CDG81_13160

» show all

Reference

1 [PMID:16218575]

Authors

Yuan Y, Chung HS, Leimkuhler C, Walsh CT, Kahne D, Walker S

Title

In vitro reconstitution of EryCIII activity for the preparation of unnatural macrolides.

Journal

J Am Chem Soc 127:14128-9 (2005)
DOI:10.1021/ja053704n

Sequence

[sen:SACE_0726]

Reference

2 [PMID:15303858]

Authors

Lee HY, Chung HS, Hang C, Khosla C, Walsh CT, Kahne D, Walker S

Title

Reconstitution and characterization of a new desosaminyl transferase, EryCIII, from the erythromycin biosynthetic pathway.

Journal

J Am Chem Soc 126:9924-5 (2004)
DOI:10.1021/ja048836f

Sequence

[sen:SACE_0726]

Reference

3 [PMID:22056329]

Authors

Moncrieffe MC, Fernandez MJ, Spiteller D, Matsumura H, Gay NJ, Luisi BF, Leadlay PF

Title

Structure of the glycosyltransferase EryCIII in complex with its activating P450 homologue EryCII.

Journal

J Mol Biol 415:92-101 (2012)
DOI:10.1016/j.jmb.2011.10.036

Other DBs

ExplorEnz - The Enzyme Database:

2.4.1.278

IUBMB Enzyme Nomenclature:

2.4.1.278

ExPASy - ENZYME nomenclature database:

2.4.1.278

BRENDA, the Enzyme Database:

2.4.1.278

LinkDB

REACTION: R05531

Entry

R05531                      Reaction

Name

dTDP-D-desosamine:3-O-mycarosylerythronolide-B 5-O-beta-D-desosaminyltransferase

Definition

dTDP-D-desosamine + 3-O-alpha-Mycarosylerythronolide B <=> Erythromycin D + dTDP

Equation

C11911 + C06630 <=> C06633 + C00363

Comment

desosaminyltransferase, EryCIII+EryCII, MegCIII+MegCII

Reaction class

RC00005

C00363_C11911

RC00049

C06630_C06633

Enzyme

2.4.1.278

Pathway

rn00522

Biosynthesis of 12-, 14- and 16-membered macrolides

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

Module

M00774

Erythromycin biosynthesis, propanoyl-CoA + methylmalonyl-CoA => deoxyerythronolide B => erythromycin A/B

Brite

Enzymatic reactions [BR:br08201]
2. Transferase reactions
  2.4  Glycosyltransferases
   2.4.1  Hexosyltransferases
    2.4.1.278
     R05531  dTDP-D-desosamine + 3-O-alpha-Mycarosylerythronolide B <=> Erythromycin D + dTDP

Orthology

K14368

3-alpha-mycarosylerythronolide B desosaminyl transferase [EC:2.4.1.278]

K15997

3-alpha-mycarosylerythronolide B desosaminyl transferase auxiliary protein

Reference

1 [PMID:9353926]

Authors

Summers RG, Donadio S, Staver MJ, Wendt-Pienkowski E, Hutchinson CR, Katz L.

Title

Sequencing and mutagenesis of genes from the erythromycin biosynthetic gene cluster of Saccharopolyspora erythraea that are involved in L-mycarose and D-desosamine production.

Journal

Microbiology 143:3251-62 (1997)
DOI:10.1099/00221287-143-10-3251

Reference

2 [PMID:22056329]

Authors

Moncrieffe MC, Fernandez MJ, Spiteller D, Matsumura H, Gay NJ, Luisi BF, Leadlay PF

Title

Structure of the glycosyltransferase EryCIII in complex with its activating P450 homologue EryCII.

Journal

J Mol Biol 415:92-101 (2012)
DOI:10.1016/j.jmb.2011.10.036

Reference

3 [PMID:16514147]

Authors

Rodriguez E, Peiru S, Carney JR, Gramajo H

Title

In vivo characterization of the dTDP-D-desosamine pathway of the megalomicin gene cluster from Micromonospora megalomicea.

Journal

Microbiology 152:667-73 (2006)
DOI:10.1099/mic.0.28680-0

Other DBs

RHEA:

32094

LinkDB

DBGET integrated database retrieval system