An improved procedure for the microbial hydroxylations of dehydroepiandrosterone (DHEA, 1) and 15β,16β-methylene-dehydroepiandrosterone (2) was studied using whole cells of Botryodiplodia malorum and Colletotrichum lini. C. lini catalyzed 7α- and 15α-hydroxylation of 1 and 7α-hydroxylation of 2, while B. malorum gave 7β-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 7α,15α-dihydroxy-1 production were improved obtaining 5.8 g l−1 (recovered product) from 7.0 g l−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.
Steroid hydroxylations with Botryodiplodia malorum and Colletotrichum lini / A. Romano, D. Romano, E.M. Ragg, F. Costantino, R. Lenna, R. Gandolfi, F.E. Molinari. - In: STEROIDS. - ISSN 0039-128X. - 71:6(2006), pp. 429-434.
Steroid hydroxylations with Botryodiplodia malorum and Colletotrichum lini
A. RomanoPrimo
;D. RomanoSecondo
;E.M. Ragg;R. GandolfiPenultimo
;F.E. MolinariUltimo
2006
Abstract
An improved procedure for the microbial hydroxylations of dehydroepiandrosterone (DHEA, 1) and 15β,16β-methylene-dehydroepiandrosterone (2) was studied using whole cells of Botryodiplodia malorum and Colletotrichum lini. C. lini catalyzed 7α- and 15α-hydroxylation of 1 and 7α-hydroxylation of 2, while B. malorum gave 7β-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 7α,15α-dihydroxy-1 production were improved obtaining 5.8 g l−1 (recovered product) from 7.0 g l−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.Pubblicazioni consigliate
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