Anomalous microbial transformations on the taxane ring of 10-DAB by a strain of the fungus Curvularia lunata: transbenzoylation, transacetylation, and opening of the oxetane ring.
The fermentation of 10-deacetylbaccatin III (10-DAB) (1) with Curvularia lunata afforded the taxane hemiacetals 2a and 3, characterized by extensive structural modification, including C-2 to C-1 transbenzoylation, oxidation of the C-2 hydroxyl, formation of a C-9/C13 hemiacetal, epimerization at C-10, and migration of the endocyclic double bond to an exocyclic location. In compound 3, an acetate-assisted opening of the oxetane ring was also observed.
Arnone
Alberto
A
CNR-ICRM, Department of Chemistry, Materials and Chemical Engineering, Politecnico di Milano, via Mancinelli, 7, 20131, Milano, Italy.
Bava
Adriana
A
Fronza
Giovanni
G
Nasini
Gianluca
G
D001203:Ascomycota / Q000378:metabolism*; D001711:Biotransformation; D001952:Bridged-Ring Compounds / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D043823:Taxoids / Q000737:chemistry*
D001952:Bridged-Ring Compounds; D004988:Ethers, Cyclic; D043823:Taxoids; C080625:taxane; C042213:10-deacetylbaccatine III; C005287:oxetane