Synthesis and antifungal activity of rhodopeptin analogues. 1. Modification of the east and south amino acid moieties

Org Lett. 2000 Apr 6;2(7):973-6. doi: 10.1021/ol005631c.

Abstract

Structure-activity relationships of the east and south amino acid modified analogues of rhodopeptins, novel antifungal cyclic tetrapeptides isolated from Rhodococcus species Mer-N1033, have been investigated. It was observed that a basic amino acid moiety (lysine or ornithine) as the east amino acid and a hydrophobic and bulky neutral amino acid (i.e., gamma-methylleucine) as the south amino acid were indispensable structure motifs for antifungal activity of rhodopeptin analogues.

MeSH terms

  • Amino Acids / chemistry*
  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / pharmacology
  • Fungi / drug effects
  • Microbial Sensitivity Tests
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / pharmacology
  • Rhodococcus / chemistry
  • Structure-Activity Relationship

Substances

  • Amino Acids
  • Antifungal Agents
  • Peptides, Cyclic
  • rhodopeptin B5