Novel 4,5-dihydro-thiazinogeldanamycin in a gdmP mutant strain of Streptomyces hygroscopicus 17997

Biosci Biotechnol Biochem. 2011;75(10):2042-5. doi: 10.1271/bbb.110361. Epub 2011 Oct 7.

Abstract

Novel geldanamycin derivative, 4,5-dihydro-thiazinogeldanamycin (3), was characterized from the gdmP mutant in Streptomyces hygroscopicus 17997, besides expected 4,5-dihydro-geldanamycin (2). The presence of this compound would suggest an unknown post-PKS modification in geldanamycin biosynthesis. Compound 3 exhibited moderate anti-HSV-1-virus activity and higher water solubility than geldanamycin (1). Cysteine served as a precursor to synthesize 3, whose formation required obligatory enzymatic assistance.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacterial Proteins / genetics*
  • Bacterial Proteins / metabolism*
  • Benzoquinones / chemistry*
  • Benzoquinones / metabolism*
  • Lactams, Macrocyclic / chemistry*
  • Lactams, Macrocyclic / metabolism*
  • Mutation*
  • Protein Engineering
  • Streptomyces / genetics*
  • Streptomyces / metabolism*
  • Thiazines / chemistry*
  • Thiazines / metabolism*

Substances

  • 4,5-dihydrothiazinogeldanamycin
  • Bacterial Proteins
  • Benzoquinones
  • Lactams, Macrocyclic
  • Thiazines
  • geldanamycin