title: Synthesis of quaternary-carbon-containing and functionalized enantiopure pentanecarboxylic acids from biocatalytic desymmetrization of meso-cyclopentane-1,3-dicarboxamides.
abstract: Catalyzed by Rhodococcus erythropolis AJ270, a nitrile hydratase-amidase containing microbial whole-cell catalyst under mild conditions, enantioselective desymmetrizations of meso-cyclopentane-1,3-dicarbonitriles and cyclopentane-1,3-dicarboxamides were studied. Although the nitrile hydratase was found to exhibit high enzymatic activity, but low 1R enantioselectivity toward dinitriles, a number of 2,2-unsymmetrically substituted meso-cyclopentane-1,3-dicarboxamide substrates were converted by the 1S enantioselective amidase into quaternary carbon-bearing enantiopure (1S,2R,3R)-3-carbamoylcyclopentanecarboxylic acids in yields up to 94 %. The application of the method was demonstrated by convenient and practical transformations of the resulting (1S,2R,3R)-2-allyl-3-carbamoylcyclopentanecarboxylic acid derivatives into functionalized cyclopentane-fused δ-lactam and δ-lactone compounds.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (P.R. China).
authors.forename: Yu-Fei
authors.initials: YF
authors.lastname: Ao
authors.forename: De-Xian
authors.initials: DX
authors.lastname: Wang
authors.forename: Liang
authors.initials: L
authors.lastname: Zhao
authors.forename: Mei-Xiang
authors.initials: MX
authors.lastname: Wang
mesh_terms: D001711:Biotransformation; D002264:Carboxylic Acids / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D002384:Catalysis; D008958:Models, Molecular; D015394:Molecular Structure; D012240:Rhodococcus / Q000378:metabolism
chemical_list: D002264:Carboxylic Acids
keywords: biotransformations; cyclopentanes; desymmetrization; enantioselectivity; enzymes