Substrate specificity of 2-deoxy-scyllo-inosose synthase, the starter enzyme for 2-deoxystreptamine biosynthesis, toward deoxyglucose-6-phosphates and proposed mechanism

Noriaki Iwase, Fumitaka Kudo, Noriaki Yamauchi, Katsumi Kakinuma

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

A crucial enzyme in the biosynthesis of the 2-deoxystreptamine aglycon of clinically important aminocyclitol antibiotics is 2-deoxy-scyllo-inosose synthase (DOIS), which is responsible for the initial carbocycle formation of 2-deoxy-scyllo-inosose (1) from D-glucose-6-phosphate (G-6-P) (2). To get more insight into the mechanism and substrate specificity, deoxy-D-glucose-6-phosphates (deoxy-G-6-P) were chemically synthesized and subjected to the reaction with DOIS. The enzyme appeared to use 2-deoxy- and 3-deoxy-G-6-P as substrates, both of which were converted into the corresponding dideoxy-scyllo-inosose products, but 4-deoxy-G-6-P failed in cyclization by DOIS. These results clearly support the proposed reaction mechanism involving the initial oxidation at C-4 of the G-6-P substrate. Another implication is the potential use of DOIS for the preparation of useful dideoxyinososes.

Original languageEnglish
Pages (from-to)2396-2407
Number of pages12
JournalBioscience, Biotechnology and Biochemistry
Volume62
Issue number12
DOIs
Publication statusPublished - Jan 1 1998

Fingerprint

Glucose-6-Phosphate
Starters
Biosynthesis
Substrate Specificity
Phosphates
Substrates
Enzymes
Glucose
Cyclization
2-deoxy-scyllo-inosose synthase
6-deoxyglucose
2-deoxystreptamine
Anti-Bacterial Agents
Oxidation

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

Cite this

Substrate specificity of 2-deoxy-scyllo-inosose synthase, the starter enzyme for 2-deoxystreptamine biosynthesis, toward deoxyglucose-6-phosphates and proposed mechanism. / Iwase, Noriaki; Kudo, Fumitaka; Yamauchi, Noriaki; Kakinuma, Katsumi.

In: Bioscience, Biotechnology and Biochemistry, Vol. 62, No. 12, 01.01.1998, p. 2396-2407.

Research output: Contribution to journalArticle

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