Biotransformation of a 4(20),11(12)-taxadiene derivative

A 4(20),11(12)-taxadiene derivative was converted to hydroxylated derivatives by Cunninghamella elegans AS3.2033 and Cunninghamella elegans var chibaensis ATCC 20230. Both microorganisms led to C-1 hydroxylations and conversion to a C-15-hydroxylated abeo-taxane. Additional products from the two fun...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2001-03, Vol.9 (3), p.793-800
Main Authors: Sun, Di-An, Sauriol, Françoise, Mamer, Orval, Zamir, Lolita O.
Format: Article
Language:English
Subjects:
Alkenes - metabolism
Antineoplastic Agents - metabolism
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Biotransformation
Bridged-Ring Compounds - metabolism
Cunninghamella - metabolism
Diterpenes - metabolism
Fundamental and applied biological sciences. Psychology
Fungi - metabolism
Hydroxylation
Magnetic Resonance Spectroscopy
Methods. Procedures. Technologies
Paclitaxel - analogs & derivatives
Paclitaxel - metabolism
Stereoisomerism
Substrate Specificity
Taxoids
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Summary:A 4(20),11(12)-taxadiene derivative was converted to hydroxylated derivatives by Cunninghamella elegans AS3.2033 and Cunninghamella elegans var chibaensis ATCC 20230. Both microorganisms led to C-1 hydroxylations and conversion to a C-15-hydroxylated abeo-taxane. Additional products from the two fungi differed: a C-14 oxidation and a trans–cis isomerization of the cinnamoyl for one and an unprecedented hydroxylation at C-17 for the other. Efficient biotransformations of taxane derivative 1 to C-1 hydroxylation and C-15-hydroxylated abeo-taxane and low yields unusual reactions are described.
ISSN:0968-0896
1464-3391
DOI:10.1016/S0968-0896(00)00299-6