Practical synthesis of optically active alpha,alpha-disubstituted malonamic acids through asymmetric hydrolysis of malonamide derivatives with Rhodococcus sp. CGMCC 0497.
A variety of alpha,alpha-disubstituted malonamides undergo enantioselective hydrolysis with Rhodococcus sp. CGMCC 0497 to give challenging enantiopure alpha,alpha-disubstituted malonamic acids with up to >99% enantiomeric excesses and 98% chemical yields. The enantioselectivity originated from the effects of a highly enantioselective amidase. The products could be converted to valuable (R)- or (S)-alpha,alpha-dialkylated amino acids after routine conversions.
Wu
Zhong-Liu
ZL
State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Li
Zu-Yi
ZY
D000581:Amidohydrolases / Q000378:metabolism*; D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D006868:Hydrolysis; D008314:Malonates / Q000032:analysis / Q000138:chemical synthesis* / Q000378:metabolism; D015394:Molecular Structure; D012240:Rhodococcus / Q000201:enzymology / Q000378:metabolism*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000596:Amino Acids; D008314:Malonates; C013098:malonamic acid; D000581:Amidohydrolases; C019665:amidase; C008314:malonamide