Efficient hydroxylation of functionalized steroids by Colletotrichum lini ST-1

Add time:08/21/2019    Source:sciencedirect.com

Biotransformation of a series of steroid compounds (estradiol, estrone, androst-4-en-3,17-dione, testosterone, canrenone, 16α,17α-epoxyprogesterone and progesterone) with Colletotrichum lini ST-1 as biocatalyst was investigated. With the exception of estradiol, estrone and progesterone, the microorganism could selectively hydroxylate steroid substrates (4 g/L) with 70–85% conversion rate and 60–76% total products yield. The different hydroxylation sites between androst-4-en-3,17-dione (3) and testosterone (4) suggested that the hydroxyl group or carbonyl group on the substrate at C17 had profound influence on the location of introduced hydroxyl groups. Transformations of 3-keto-steroid (3, 4, 5, 6 and 7) included monohydroxylation or dihydroxylation at 11α and 15α positions, while hydroxylations of 3-hydroxy-steroid (DHEA) were hydroxylation at 7α and 15α positions. Moreover, time course experiments demonstrated dihydroxylation of androst-4-en-3,17-dione (3), canrenone (5) and 16α,17α-epoxyprogesterone (6) were all initiated by hydroxylation on ring-D (C15) followed by attack on ring-C (C11). In this study, several new hydroxylation products were discovered, including 11α,15α-dihydroxyandrost-4-en-3,17-dione (9), 11α,15α-dihydroxy-canrenone (12) and 11α,15α-dihydroxy-16α,17α-epoxyprogesterone (14). The breadth of substrate spectrum and the excellent conversion rates achieved with this fungus indicated that C. lini ST-1 was a potential microorganism for production of valuable pharmaceutical ingredients and precursors.

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