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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Veröffentlicht in:	Bioorganic & medicinal chemistry 2001-03, Vol.9 (3), p.793-800
Hauptverfasser:	Sun, Di-An, Sauriol, Françoise, Mamer, Orval, Zamir, Lolita O.
Format:	Artikel
Sprache:	eng
Schlagworte:	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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Zusammenfassung:	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