Optical Resolution of a d-Biotin Chiral Intermediate by Use of Lipoprotein Lipase

Article abstract of DOI:10.1246/cl.1993.741

An efficient optical resolution of (+/-)-3aα,4α,6aα)-1,3-dibenzyl-3a,4,6,6a-tetrahydro-4-hydroxy-1H-thieno<3,4-d>imidazol-2(3H)-one <(RS)-1> was accomplished by acylation with lipoprotein lipase from Pseudomonas aeruginosa TE3285 in toluene. The lipase acylated (R)-1 enantioselectively, and unreacted (S)-1, which is a chiral d-biotin intermediate, was isolated in excellent chemical and optical yields (>99percent e.e.). Effects of acylating agents, water content and molecular sieves were also investigated.