Enzymatic desymmetrization of a meso polyol corresponding to the C(19)-C(27) segment of rifamycin S.
The stereoselective acylation of meso polyol 2 by vinyl acetate (solvent and acyl donor) in the presence of porcine pancreas lipase gave the corresponding monoester 5 in good yield (76%) and high enantiomeric purity (ee > 98%). The enzymatic reaction was also highly regioselective for a primary alcohol end group, and the two unprotected secondary alcohols were not involved. Compound 5 corresponds to the C(19)-C(27) fragment of rifamycin S.
Chênevert
R
R
Département de chimie, Faculté des sciences et de génie, Université Laval, Québec, Canada.
Rose
Y S
YS
D000215:Acylation; D000438:Alcohols / Q000737:chemistry / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000737:chemistry; D001665:Binding Sites; D016956:Burkholderia cepacia / Q000201:enzymology; D012321:DNA-Directed RNA Polymerases / Q000037:antagonists & inhibitors; D005461:Fluorine; D005765:Gastrointestinal Agents / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D020799:Pancrelipase / Q000378:metabolism*; D011551:Pseudomonas fluorescens / Q000201:enzymology; D012294:Rifamycins / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000378:metabolism
D000438:Alcohols; D000900:Anti-Bacterial Agents; D005765:Gastrointestinal Agents; D012294:Rifamycins; D014753:Vinyl Compounds; D005461:Fluorine; D020799:Pancrelipase; D012321:DNA-Directed RNA Polymerases; C011566:vinyl acetate; C032779:rifamycin S