Regio- and stereoselective hydroxylation of taxoids by filamentous fungi.
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 1beta and 9alpha 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.
Hu
Shanghui
S
Institute of Materia Medica, Chinese Academy of Medical Sciences and Perking Union Medical College, Beijing 100050, China. shanghuihu@hotmail.com
Sun
Di-An
DA
Tian
Xufang
X
Fang
Qicheng
Q
D020095:Absidia / Q000378:metabolism; D001711:Biotransformation; D001952:Bridged-Ring Compounds / Q000737:chemistry* / Q000378:metabolism*; D005658:Fungi / Q000378:metabolism*; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D017239:Paclitaxel / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism; D043823:Taxoids
D001952:Bridged-Ring Compounds; D043823:Taxoids; C080625:taxane; D017239:Paclitaxel