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Ligand desvancosaminyl-vancomycin

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.311

dTDP-beta-L-4-epi-vancosamine + devancosaminyl-vancomycin = dTDP + chloroorienticin B

723618, 723620

-

2.4.1.322

dTDP-beta-L-vancosamine + devancosaminyl-vancomycin = dTDP + vancomycin

721585, 724268

-

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.310

UDP-alpha-D-glucose + vancomycin aglycone = UDP + devancoaminyl vancomycin

0

-

Substrate in Enzyme-catalyzed Reactions (10 results)

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Show Substrate (10 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.311

dTDP-beta-L-4-epi-vancosamine + desvancosaminyl-vancomycin = dTDP + chloroorienticin B

723620

-

2.4.1.311

dTDP-beta-L-4-epi-vancosamine + devancosaminyl-vancomycin = dTDP + chloroorienticin B

723618, 723620

-

2.4.1.322

dTDP-beta-L-vancosamine + desvancosaminyl-vancomycin = dTDP + vancomycin

736938

-

2.4.1.322

UDP-beta-L-vancosamine + desvancosaminyl-vancomycin = dUDP + vancomycin

736938

-

2.4.1.322

dTDP-beta-L-acosamine + devancosaminyl-vancomycin = dTDP + ?

727659

-

2.4.1.322

dTDP-beta-L-daunosamine + devancosaminyl-vancomycin = dTDP + ?

727659

-

2.4.1.322

dTDP-beta-L-vancosamine + devancosaminyl-vancomycin = dTDP + vancomycin

721585, 727292, 727659, 724268

-

2.4.1.322

UDP-4-epi-L-vancosamine + devancosaminyl-vancomycin = UDP + epi-L-vancomycin

727659

-

2.4.1.322

UDP-4-epi-vancosamine + devancosaminyl-vancomycin = UDP + epivancomycin

721585, 727292

-

2.4.1.322

UDP-L-epi-vancosamine + devancosaminyl-vancomycin = UDP + ?

724268

-

2.4.1.311

2 entries

2.4.1.322

8 entries

Product in Enzyme-catalyzed Reactions (1 result)

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Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.310

UDP-alpha-D-glucose + vancomycin aglycone = UDP + devancoaminyl vancomycin

0

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (3 results)

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Show Turnover Number (3 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.4.1.311

0.038

-

pH 7.5, 37°C

723620

2.4.1.322

0.002

-

pH 7.0, 37°C, mutant enzyme D13A

724268

2.4.1.322

1.12

-

pH 7.0, 37°C, wild-type enzyme

724268

2.4.1.322

2 entries

K_M Value (3 results)

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Show KM Value (3 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.4.1.311

0.107

-

pH 7.5, 37°C

723620

2.4.1.322

0.016

-

pH 7.0, 37°C, wild-type enzyme

724268

2.4.1.322

0.027

-

pH 7.0, 37°C, mutant enzyme T10A

724268

2.4.1.322

2 entries

References & Links

Literature References (7)

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Show Reference (7 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

721585

11294642

Tandem action of glycosyltransferases in the maturation of vancomycin and teicoplanin aglycones: novel glycopeptides

2001

Losey, H.C.; Peczuh, M.W.; Chen, Z.; Eggert, U.S.; Dong, S.D.; Pelczer, I.; Kahne, D.; Walsh, C.T.

Biochemistry

40

4745-4755

723618

12874381

Structure of the TDP-epi-vancosaminyltransferase GtfA from the chloroeremomycin biosynthetic pathway

2003

Mulichak, A.M.; Losey, H.C.; Lu, W.; Wawrzak, Z.; Walsh, C.T.; Garavito, R.M.

Proc. Natl. Acad. Sci. USA

100

9238-9243

723620

15070728

Characterization of a regiospecific epivancosaminyl transferase GtfA and enzymatic reconstitution of the antibiotic chloroeremomycin

2004

Lu, W.; Oberthür, M.; Leimkuhler, C.; Tao, J.; Kahne, D.; Walsh, C.T.

Proc. Natl. Acad. Sci. USA

101

4390-4395

724268

15122882

Crystal structure of vancosaminyltransferase GtfD from the vancomycin biosynthetic pathway: interactions with acceptor and nucleotide ligands

2004

Mulichak, A.M.; Lu, W.; Losey, H.C.; Walsh, C.T.; Garavito, R.M.

Biochemistry

43

5170-5180

727292

12498883

Incorporation of glucose analogs by GtfE and GtfD from the vancomycin biosynthetic pathway to generate variant glycopeptides

2002

Losey, H.C.; Jiang, J.; Biggins, J.B.; Oberthuer, M.; Ye, X.Y.; Dong, S.D.; Kahne, D.; Thorson, J.S.; Walsh, C.T.

Chem. Biol.

9

1305-1314

727659

16045364

A systematic investigation of the synthetic utility of glycopeptide glycosyltransferases

2005

Oberthuer, M.; Leimkuhler, C.; Kruger, R.G.; Lu, W.; Walsh, C.T.; Kahne, D.

J. Am. Chem. Soc.

127

10747-10752

736938

24954524

Enzymatic glycosylation of vancomycin aglycon: completion of a total synthesis of vancomycin and N- and C-terminus substituent effects of the aglycon substrate

2014

Nakayama, A.; Okano, A.; Feng, Y.; Collins, J.C.; Collins, K.C.; Walsh, C.T.; Boger, D.L.

Org. Lett.

16

3572-3575

Links to other databases for desvancosaminyl-vancomycin

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Show Links (1 entry)

ChEBI

PubChem