Dramatic enhancement of enantioselectivity of biotransformations of beta-hydroxy nitriles using a simple O-benzyl protection/docking group.
[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.
Ma
Da-You
DY
Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China.
Zheng
Qi-Yu
QY
Wang
De-Xian
DX
Wang
Mei-Xiang
MX
D000577:Amides / Q000737:chemistry; D001555:Benzene Derivatives / Q000737:chemistry*; D001711:Biotransformation; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D002384:Catalysis; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D012240:Rhodococcus / Q000378:metabolism*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000577:Amides; D001555:Benzene Derivatives; D002264:Carboxylic Acids; D009570:Nitriles