Biosynthesis of spinosyn in saccharopolyspora spinosa: Synthesis of permethylated rhamnose and characterization of the functions of SpnH, Spnl, and SpnK

Hak Joong Kim, Jess A. White-Phillip, Yasushi Ogasawara, Nara Shin, Eta A. Isiorho, Hung Wen Liu

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

(Figure Presented) Spinosyn A is a polyketide-derived macrolide produced by Saccharopolyspora spinosa and is an active ingredient in several commercial insecticides. It is glycosylated by a tri-O-methylated rhamnose at C-9 and a forosamine at C-17. Previous studies indicated that the rhamnose methyltransferases are encoded by the spnH, spnI, and spnK genes. To verify the functions of these methyltransferases and to study how they are coordinated to achieve the desired level of methylation of rhamnose, we studied the catalytic properties of the spnH, spnI, and spnK gene products and validated their roles in the permethylation process of spinosyn A. Our data reported herein firmly established that SpnH, SpnI, and SpnK are the respective rhamnose 4′-, 2′-, and 3′-O-methyltransferase. Investigation of the order of the methylation events revealed that only one route catalyzed by SpnI, SpnK, and SpnH in sequence is productive for the permethylation of the rhamnose moiety. Moreover, the completion of rhamnose permethylation is likely achieved by the proper control of the expression levels of the methyltransferase genes involved. These results set the stage for future exploitation of the spinosyn biosynthetic pathway to produce targeted spinosyn derivatives and, perhaps, new analogues.

Original languageEnglish
Pages (from-to)2901-2903
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number9
DOIs
Publication statusPublished - 2010 Mar 10
Externally publishedYes

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Biosynthesis of spinosyn in saccharopolyspora spinosa: Synthesis of permethylated rhamnose and characterization of the functions of SpnH, Spnl, and SpnK'. Together they form a unique fingerprint.

  • Cite this