BIOSYNTHESIS OF A MEYTHYIOLINCOSAMINIDE

Project: Research project

Project Details

Description

Alpha-Methylthiolincosaminide (MTL) is the octose moiety of the clinically
important lincomycin antibiotics. Previous studies have demonstrated that
MTL (C8 unit) is biosynthetically derived from condensation of a C5 unit
such as ribose-5-phosphate with a C3 donor molecule such as
sedoheptulose-7-phosphate probably by a transaldolase reaction. The
proposed investigation will examine in detail the biosynthetic steps
between condensation of the C5 unit and C3 unit and the formation of MTL by
Streptomyces lincolnensis. Using primarily 13C-NMR we propose to identify both the C5 unit and the C3
donor molecule which condense to form the purported octulose-8-phosphate
and in turn its conversion to octose-8-phosphate. A retrospective
biosynthetic analysis leads us to suspect that the 8-deoxyoctose may be
formed by an analogous reaction to the TDP-D-glucose oxidoreductase
reaction. We will examine this possibility and determine the
stereochemical course of the reaction by analysis of the chiral C-8 methyl
group produced in MTL. Lastly we propose to examine the origin of the
S-CH3 found in MTL.
StatusFinished
Effective start/end date9/30/868/31/89

Funding

  • National Institutes of Health
  • National Institutes of Health
  • National Institutes of Health

ASJC

  • Medicine(all)
  • Immunology and Microbiology(all)

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