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New approach to regioselective synthesis: Using proteins in vitro as guidance—regioselective reduction of steroids with guidance from bovine serum albumin
Author(s) -
Liu XiaoChuan,
Kayser Lauren
Publication year - 2003
Publication title -
biotechnology and bioengineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.136
H-Index - 189
eISSN - 1097-0290
pISSN - 0006-3592
DOI - 10.1002/bit.10636
Subject(s) - regioselectivity , bovine serum albumin , chemistry , steroid , yield (engineering) , reactivity (psychology) , combinatorial chemistry , organic chemistry , chromatography , biochemistry , catalysis , materials science , medicine , alternative medicine , pathology , hormone , metallurgy
A novel approach for regioselective synthesis is described. The approach uses the unique binding properties of protein as a guide to achieve regioselectivity. Specifically, steroids, e.g., 4‐androstene‐3,17‐dione, were reduced selectively at carbon 17 using bovine serum albumin (BSA) as a regio auxlliary. The approach has resulted in a high yield (ca. 91%) in an environmental friendly aqueous medium. Both 1 H NMR and 13 C NMR data show that the BSA‐assisted reduction of the steroid render the reaction regioselective compared to the control reaction. Various control reactions were performed to verify that the unique binding of BSA to steroids was the origin of regioselectivity. After one cycle of the reduction reaction, BSA was reconditioned such that it could be reused five or more times. This novel approach could be used to develop practical and “green” methods for regioselective synthesis. © 2003 Wiley Periodicals, Inc. Biotechnol Bioeng 82: 858–863, 2003.