Preparation of optically-active 3-pyrrolidinol and its derivatives from 1-benzoylpyrrolidinol by hydroxylation with Aspergillus sp and stereo-selective esterification by a commercial lipase

Yamada S; Shimada H; Yamada R; Shiratori-Takano H; Sayo N; Saito T; Takano H; Beppu T; Ueda K

Biotechnology Letters, Vol.36, No.3, 595-600, 2014

DOI10.1007/s10529-013-1394-0 Export Citation

Preparation of optically-active 3-pyrrolidinol and its derivatives from 1-benzoylpyrrolidinol by hydroxylation with Aspergillus sp and stereo-selective esterification by a commercial lipase

Yamada S, Shimada H, Yamada R, Shiratori-Takano H, Sayo N, Saito T, Takano H, Beppu T, Ueda K

An effective preparation scheme for optically-active 3-pyrrolidinol and its derivatives based on biological transformation is proposed. Aspergillus sp. NBRC 109513 hydroxylated 1-benzoylpyrrolidine, yielding (S)-1-benzoyl-3-pyrrolidinol with 66 % ee. Kinetic resolution of 1-benzoyl-3-pyrrolidinol by Amano PS-IM lipase formed optically-active 1-benzoyl-3-pyrrolidinol with > 99 % ee. (S)-1-Benzoyl-3-pyrrolidinol was successfully converted to 3-pyrrolidinol and its derivatives with by chemical reactions (> 99 % ee).

Keywords:Aspergillus;1-Benzoylpyrrolidine;Biotransformation;Hydroxylation;Lipase;3-Pyrrolidinol;Stereoselective enzymatic esterification