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Regio‐ and stereoselective hydroxylation of taxoids by filamentous fungi
Author(s) -
Hu Shanghui,
Sun DiAn,
Tian Xufang,
Fang Qicheng
Publication year - 2002
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10078
Subject(s) - chemistry , hydroxylation , stereoselectivity , taxane , stereochemistry , paclitaxel , aspergillus nidulans , oxetane , epothilones , combinatorial chemistry , organic chemistry , catalysis , enzyme , biochemistry , cancer , mutant , gene , medicine , breast cancer
Paclitaxel (Taxol ® ), is one of the most promising chemotherapeutic agents developed for cancer treatment in past two decades. Microorganisms such as filamentous fungi are known to perform regio‐ and stereoselective hydroxylation of taxoids. Herein, we describe highly regio‐ and stereoselective hydroxylation at the 1β and 9α positions of the taxane skeleton. Such hydroxylation reactions proceed readily for the taxadienes as substrates rather than taxoids having an oxetane ring. The presence of different oxygen substituents on the taxane nucleus, such as 5‐acetoxy, has a significant effect on the selectivity and yield of the hydroxylation catalyzed by the microbial oxidases. Chirality 14:495–497, 2002. © 2002 Wiley‐Liss, Inc.