Elucidation of the glycosylation steps during biosynthesis of antitumor macrolides PM100117 and PM100118 and engineering for novel derivatives

Microb Cell Fact. 2016 Nov 9;15(1):187. doi: 10.1186/s12934-016-0591-7.

Abstract

Background: Antitumor compounds PM100117 and PM100118 are glycosylated polyketides derived from the marine actinobacteria Streptomyces caniferus GUA-06-05-006A. The organization and characterization of the PM100117/18 biosynthesis gene cluster has been recently reported.

Results: Based on the preceding information and new genetic engineering data, we have outlined the pathway by which PM100117/18 are glycosylated. Furthermore, these genetic engineering experiments have allowed the generation of novel PM100117/18 analogues. Deletion of putative glycosyltranferase genes and additional genes presumably involved in late biosynthesis steps of the three 2,6-dideoxysugars appended to the PM100117/18 polyketide skeleton, resulted in the generation of a series of intermediates and novel derivatives.

Conclusions: Isolation and identification of the novel compounds constitutes an important contribution to our knowledge on PM100117/18 glycosylation, and set the basis for further characterization of specific enzymatic reactions, additional genetic engineering and combinatorial biosynthesis approaches.

Keywords: Antitumor; Deoxysugar; Glycosyltranferase; Structural analogue.

MeSH terms

  • A549 Cells
  • Antineoplastic Agents / metabolism*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Gene Deletion
  • Genetic Engineering / methods*
  • Glycosylation
  • Glycosyltransferases / genetics
  • Glycosyltransferases / metabolism
  • HT29 Cells
  • Humans
  • Macrolides / metabolism*
  • Macrolides / pharmacology
  • Streptomyces / genetics
  • Streptomyces / metabolism

Substances

  • Antineoplastic Agents
  • Macrolides
  • PM100117
  • PM100118
  • Glycosyltransferases