Synthesis of novel lysophosphatidylcholine analogues using serine as chiral template

J Org Chem. 2003 Dec 26;68(26):10162-5. doi: 10.1021/jo034969s.

Abstract

Four novel lysophosphatidylcholine (lysoPC) analogues, (S)-N-stearoyl-O-phosphocholineserine methyl ester [(S)-1a], (R)-1-lyso-2-stearoylamino-2-deoxy-sn-glycero-3-phosphatidylcholine [(R)-2a], (R)-N-stearoyl-O-phosphocholineserine methyl ester [(R)-1b], and (S)-1-lyso-2-stearoylamino-2-deoxy-sn-glycero-3-phosphatidylcholine [(S)-2b], were synthesized starting from serine as a chiral template. These synthetic compounds exhibited greatly enhanced hyphal transition inhibitory activity in Candida as compared to the natural lysoPC.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amphotericin B / pharmacology
  • Animals
  • Calcium / metabolism
  • Candida / drug effects
  • Candida / genetics
  • Candida / growth & development
  • Drug Synergism
  • Humans
  • Inhibitory Concentration 50
  • Lymphocytes / drug effects
  • Lymphocytes / metabolism
  • Lysophosphatidylcholines / chemical synthesis*
  • Lysophosphatidylcholines / chemistry
  • Lysophosphatidylcholines / pharmacology
  • Microbial Sensitivity Tests
  • Serine / chemistry*
  • Spleen / cytology
  • Spleen / drug effects
  • Spleen / metabolism
  • Stereoisomerism

Substances

  • Lysophosphatidylcholines
  • Serine
  • Amphotericin B
  • Calcium