Diolmycins, new anticoccidial agents produced by Streptomyces sp. II. Structure elucidation of diolmycins A1, A2, B1 and B2, and synthesis of diolmycin A1

J Antibiot (Tokyo). 1993 May;46(5):762-9. doi: 10.7164/antibiotics.46.762.

Abstract

The structures of diolmycins A1, A2, B1 and B2, novel anticoccidial agents, were determined by spectroscopic analyses. Diolmycins A1 and A2 are stereoisomers with the structure of 1-(3-indolyl)-4-(p-hydroxyphenyl)-2,3-butanediol. From the chemical synthesis of the erythro-isomer, the relative configurations of diolmycins A1 and A2 were determined to be the erythro- and threo-isomers, respectively. The stereoisomers, diolmycins B1 and B2, were also deduced to be erythro- and threo-1,4-di-(p-hydroxyphenyl)-2,3-butanediol, respectively.

Publication types

  • Comparative Study

MeSH terms

  • Butylene Glycols / chemical synthesis
  • Butylene Glycols / chemistry*
  • Coccidiostats / chemical synthesis
  • Coccidiostats / chemistry*
  • Coccidiostats / isolation & purification
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Phenols / chemistry*
  • Stereoisomerism
  • Streptomyces / chemistry*

Substances

  • Butylene Glycols
  • Coccidiostats
  • Indoles
  • Phenols
  • 1,4-di-(4-hydroxyphenyl)-2,3-butanediol
  • diolmycin A1