Absolute configuration of a polyol fragment of blasticidin A, a specific inhibitor of aflatoxin production.
Blasticidin A (1) and aflastatin A (2), Streptomyces metabolites with similar structures, are specific inhibitors of aflatoxin production by Aspergillus parasiticus. The stereochemistry of the polyol fragment of 1 (3a) containing ten chiral centers was elucidated by applying acetonide and MTPA methods to a variety of acetonide derivatives of 3a, which determined the absolute configuration of 3a. By using the similar methods, the absolute configuration of the polyol fragment of 2 (4a) was determined, which was the same as that elucidated by J-based and other chemical methods previously.
Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Japan. asakuda@mail.ecc.u-tokyo.ac.jp
Shohei
S
Sakuda
Hiroyuki
H
Ikeda
Takefumi
T
Nakamura
Hiromichi
H
Nagasawa
D000348:Aflatoxins / Q000096:biosynthesis*; D001230:Aspergillus / Q000187:drug effects* / Q000378:metabolism*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D011108:Polymers / Q000737:chemistry*; D011487:Protein Conformation; D011760:Pyrrolidinones / Q000737:chemistry* / Q000494:pharmacology; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D013302:Streptomyces / Q000378:metabolism*
D000348:Aflatoxins; D007202:Indicators and Reagents; D011108:Polymers; D011760:Pyrrolidinones; C105377:aflastatin A; C420726:blasticidin A; C024617:polyol