Steroid hydroxylations with Botryodiplodia malorum and Colletotrichum lini.
An improved procedure for the microbial hydroxylations of dehydroepiandrosterone (DHEA, 1) and 15 beta,16 beta-methylene-dehydroepiandrosterone (2) was studied using whole cells of Botryodiplodia malorum and Colletotrichum lini. C. lini catalyzed 7 alpha- and 15 alpha-hydroxylation of 1 and 7 alpha-hydroxylation of 2, while B. malorum gave 7 beta-hydroxylation of both the substrates. The stability of the enzymatic activity was higher in the presence of co-substrates (i.e., glucose or mannitol) allowing for repeated batches of the biotransformations. The yields of 7 alpha,15 alpha-dihydroxy-1 production were improved obtaining 5.8 gl(-1) (recovered product) from 7.0 gl(-1) of substrate. The structures of the hydroxylated products were assigned by a combination of two-dimensional NMR proton-proton and proton-carbon correlation techniques.
Romano
Andrea
A
Dipartimento di Scienze e Tecnologie Alimentari e Microbiologiche, Università degli Studi di Milano, via Celoria 2, 20133 Milano, Italy.
Romano
Diego
D
Ragg
Enzio
E
Costantino
Francesca
F
Lenna
Roberto
R
Gandolfi
Raffaella
R
Molinari
Francesco
F
D001711:Biotransformation; D020231:Colletotrichum / Q000166:cytology / Q000378:metabolism*; D003687:Dehydroepiandrosterone / Q000737:chemistry / Q000378:metabolism; D006900:Hydroxylation; D003904:Mitosporic Fungi / Q000166:cytology / Q000378:metabolism*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013256:Steroids / Q000737:chemistry / Q000378:metabolism*; D013379:Substrate Specificity
D013256:Steroids; D003687:Dehydroepiandrosterone