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  • Title: Dramatic enhancement of enantioselectivity of biotransformations of beta-hydroxy nitriles using a simple O-benzyl protection/docking group.
    Author: Ma DY, Zheng QY, Wang DX, Wang MX.
    Journal: Org Lett; 2006 Jul 20; 8(15):3231-4. PubMed ID: 16836373.
    Abstract:
    [Structure: see text] Catalyzed by the Rhodococcus erythropolis AJ270 whole cell catalyst, the O-benzylated beta-hydroxy alkanenitriles underwent remarkably high enantioselective biotransformations, whereas the biotransformations of free beta-hydroxy alkanenitriles gave very low enantioselectivity. The easy manipulations of O-protection and O-deprotection, excellent chemical and enantiomeric yields of biotransformations, along with the scalability render this enzymatic transformation attractive and practical for the synthesis of highly enantiopure beta-hydroxy alkanoic acids and their amide derivatives.
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