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Ligand 2-deoxystreptamine

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for 2-deoxystreptamine

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Roles as Enzyme Ligand

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

2.6.1.101

L-glutamine + 3-amino-2,3-dideoxy-scyllo-inosose = 2-oxoglutaramate + 2-deoxystreptamine

-

-

Substrate in Enzyme-catalyzed Reactions (15 results)

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Show Substrate (15 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.99.38

2-deoxystreptamine + S-adenosyl-L-methionine = ? + 5'-deoxyadenosine + L-methionine

687282

-

1.3.98.3

2-deoxystreptamine + S-adenosyl-L-methionine = ? + CO2 + L-methionine + 5'-deoxyadenosine

687282

-

2.4.1.283

UDP-N-acetyl-alpha-D-glucosamine + 2-deoxystreptamine = UDP + 2'-N-acetylparomamine

719295, 720518

-

2.4.1.284

dTDP-D-glucose + 2-deoxystreptamine = ?

719134

-

2.4.1.284

GDP-D-mannose + 2-deoxystreptamine = ?

719134

-

2.4.1.284

UDP-D-galactose + 2-deoxystreptamine = ?

719134

-

2.4.1.284

UDP-D-glucose + 2-deoxystreptamine = UDP + 2'-deamino-2'-hydroxyparomamine

720518

-

2.4.1.284

UDP-N-acetyl-alpha-D-glucosamine + 2-deoxystreptamine = UDP + 2'-N-acetylparomamine

720518

-

2.6.1.50

2-deoxystreptamine + 2-ketoglutaramate = 2-deoxy-keto-inosamine + L-glutamine

640128

-

2.6.1.50

2-deoxystreptamine + 2-oxoglutaramate = 2-deoxy-scyllo-inositol + L-glutamine

640128

-

2.6.1.50

2-deoxystreptamine + keto-scyllo-inositol = 2-deoxy-scyllo-inositol + amino-deoxy-keto-scyllo-inositol

640128

-

2.6.1.50

2-deoxystreptamine + pyruvate = 2-keto-inosose + L-alanine

663004

-

2.4.1.284

5 entries

2.6.1.50

4 entries

2.7.1.65

ATP + 2-deoxystreptamine = ?

636599

-

3.1.3.39

2-deoxystreptamine + dihydrostreptomycin 6-phosphate = ?

134855

-

3.1.3.39

2-deoxystreptamine + p-nitrophenyl phosphate = ?

134855

-

3.1.3.39

2 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

2.6.1.101

L-glutamine + 3-amino-2,3-dideoxy-scyllo-inosose = 2-oxoglutaramate + 2-deoxystreptamine

-

-

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.60

weak

637302

-

Enzyme Kinetic Parameters

K_M Value (2 results)

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Show KM Value (2 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.4.1.284

0.28

-

using UDP-D-glucose as donor, in 100 mM Tris-HCl (pH 7.6), 10 mM MgCl2, 6 mM 2-mercaptoethanol, and 1 mM phenylmethylsulfonyl fluoride, at 30°C

720518

2.4.1.284

0.32

-

using UDP-N-acetyl-alpha-D-glucosamine as donor, in 100 mM Tris-HCl (pH 7.6), 10 mM MgCl2, 6 mM 2-mercaptoethanol, and 1 mM phenylmethylsulfonyl fluoride, at 30°C

720518

2.4.1.284

2 entries

K_i Value (1 result)

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Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.3.1.60

2

-

-

637302

References & Links

Literature References (9)

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Show Reference (9 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

134855

4121457

Streptomycin biosynthesis and metabolism. Phosphate transfer from dihydrostreptomycin 6-phosphate to inosamines, streptamine, and 2-deoxystreptamine

1973

Walker, J.B.; Skorvaga, M.

J. Biol. Chem.

248

2441-2446

636599

6076630

Enzymatic synthesis of streptidine from scyllo-inosamine

1967

Walker, J.B.; Walker, M.S.

Biochemistry

6

3821-3829

637302

681328

Substrate specificity and structure-activity relationships of gentamicin acetyltransferase I. The dependence of antibiotic resistance upon substrate Vmax/Km values

1978

Williams, J.W.; Northrop, D.B.

J. Biol. Chem.

253

5908-5914

640128

2729940

Reactions catalyzed by purified L-glutamine:keto-scyllo-inositol aminotransferase, an enzyme required for biosynthesis of aminocyclitol antibiotics

1989

Lucher, L.A.; Chen, Y.M.; Walker, J.B.

Antimicrob. Agents Chemother.

33

452-459

663004

15827636

The neomycin biosynthetic gene cluster of Streptomyces fradiae NCIMB 8233: characterization of an aminotransferase involved in the formation of 2-deoxystreptamine

2005

Huang, F.; Haydock, S.F.; Mironenko, T.; Spiteller, D.; Li, Y.; Spencer, J.B.

Org. Biomol. Chem.

3

1410-1418

687282

18001019

Characterization and mechanistic study of a radical SAM dehydrogenase in the biosynthesis of butirosin

2007

Yokoyama, K.; Numakura, M.; Kudo, F.; Ohmori, D.; Eguchi, T.

J. Am. Chem. Soc.

129

15147-15155

719134

18985617

Expanding substrate specificity of GT-B fold glycosyltransferase via domain swapping and high-throughput screening

2009

Park, S.H.; Park, H.Y.; Sohng, J.K.; Lee, H.C.; Liou, K.; Yoon, Y.J.; Kim, B.G.

Biotechnol. Bioeng.

102

988-994

719295

18311744

Involvement of two distinct N-acetylglucosaminyltransferases and a dual-function deacetylase in neomycin biosynthesis

2008

Yokoyama, K.; Yamamoto, Y.; Kudo, F.; Eguchi, T.

ChemBioChem

9

865-869

720518

21983602

Discovery of parallel pathways of kanamycin biosynthesis allows antibiotic manipulation

2011

Park, J.; Park, S.; Nepal, K.; Han, A.; Ban, Y.; Yoo, Y.; Kim, E.; Kim, E.; Kim, D.; Sohng, J.; Yoon, Y.

Nat. Chem. Biol.

7

843-852

Links to other databases for 2-deoxystreptamine

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Show Links (1 entry)

ChEBI

PubChem