Short-step syntheses of all stereoisomers of preussin and their bioactivities.
All the eight stereoisomers of (+)-preussin (1b), an antifungal agent inhibiting the growth of fission yeast and human cancer cells, were synthesized in two steps by non-stereoselective reactions and chromatographic separation, starting from L- and D-N-protected-phenylalaninal (2). Their bioassay revealed all of the stereoisomers to be almost equally bioactive.
Okue
Masayuki
M
Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Japan.
Watanabe
Hidenori
H
Kasahara
Koji
K
Yoshida
Minoru
M
Horinouchi
Sueharu
S
Kitahara
Takeshi
T
D000841:Anisomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D012568:Schizosaccharomyces / Q000187:drug effects; D013237:Stereoisomerism
D000935:Antifungal Agents; C058280:preussin; D000841:Anisomycin