Stereochemical Aspects of the Biosynthesis of Spectinomycin

Hideaki Otsuka, Oreste A. Mascaretti, Laurence H. Hurley, Heinz G. Floss

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

The biosynthesis of spectinomycin (1) has been studied with specifically and stereospecifically labeled glucose as precursors. The results further define the mode of conversion of glucose into the actinamine (2) moiety of 1 and show that the formation of the cyclitol portion by myo-inositol-1-phosphate synthase involves stereospecific loss of the pro-R hydrogen from C-6 of glucose 6-phosphate. The TDP-glucose oxidoreductase reaction is implicated in the formation of the 4,6-dideoxyhexose moiety of 1 by the demonstration of an intramolecular hydrogen transfer from C-4 to C-6 of the hexose, which occurs with the same stereochemistry, i.e., replacement of OH at C-6 by H-4 in an inversion mode, that has been demonstrated for the enzyme from E. coli and from another streptomycete.

Original languageEnglish (US)
Pages (from-to)6817-6820
Number of pages4
JournalJournal of the American Chemical Society
Volume102
Issue number22
DOIs
StatePublished - Sep 1980
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Stereochemical Aspects of the Biosynthesis of Spectinomycin'. Together they form a unique fingerprint.

Cite this