Synthesis of novel lysophosphatidylcholine analogues using serine as chiral template.
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.
Kim
Young-Ah
YA
Department of Chemistry, Division of Molecular Life Sciences, Ewha Womans University, Seoul 120-750, Korea.
Chung
Hae-Mi
HM
Park
Jin-Seon
JS
Choi
Wonja
W
Min
Juyoung
J
Park
Nok-Hyun
NH
Kim
Ki-Hwan
KH
Jhon
Gil-Ja
GJ
Han
So-Yeop
SY
D000666:Amphotericin B / Q000494:pharmacology; D000818:Animals; D002118:Calcium / Q000378:metabolism; D002175:Candida / Q000187:drug effects / Q000235:genetics / Q000254:growth & development; D004357:Drug Synergism; D006801:Humans; D020128:Inhibitory Concentration 50; D008214:Lymphocytes / Q000187:drug effects / Q000378:metabolism; D008244:Lysophosphatidylcholines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D012694:Serine / Q000737:chemistry*; D013154:Spleen / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D013237:Stereoisomerism
D008244:Lysophosphatidylcholines; D012694:Serine; D000666:Amphotericin B; D002118:Calcium