The relative and absolute configuration of PF1140.
A potentially general approach for elucidating the absolute configuration of N-hydroxypyridone antibiotics has been developed. One member of this family of antibiotics, PF1140, was efficiently purified from a crude fungal extract following allylation of its N-hydroxyl group. Removal of the resultant allyl group permitted regeneration of the N-hydroxyl group as well as conversion into the corresponding pyridone derivative. The stereochemistry of PF1140 including the absolute configuration was established by X-ray crystallographic analysis of the S-2-methoxy-2-(1-naphthyl)propionic ester derivative.
Fujita
Yuta
Y
Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan. hoik@sci.hokudai.ac.jp
Oguri
Hiroki
H
Oikawa
Hideaki
H
D000900:Anti-Bacterial Agents / Q000737:chemistry*; D001578:Benzopyrans / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D011728:Pyridones / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D001578:Benzopyrans; C504256:PF 1140; D011728:Pyridones