Efficient kinetic resolution of amino acids catalyzed by lipase AS ‘Amano’ via cleavage of an amide bond

Herein the efficient kinetic resolution of non-natural alpha-amino acids catalyzed by lipase AS ‘Amano’ via cleaving the amide bond is reported. The starting materials were the corresponding amino acid amides and the amino acids were generated with ees of up to 99% with E values of >600. These results indicated that the lipase AS ‘Amano’ could be a powerful amide hydrolase for the kinetic resolution of amino acid starting from the corresponding amino acid amides.

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(S)-2-Amino-3-phenylpropanoic acidC9H11NO2[α]D20=-25.9 (c 1.0, H2O)Source of chirality: kinetic resoluctionAbsolute configuration: (S)

(S)-2-Amino-3-(4-chlorophenyl)propanoic acidC9H10ClNO2[α]D20=-2.8 (c 2.15, H2O)Source of chirality: kinetic resoluctionAbsolute configuration: (S)

(S)-2-Amino-3-(4-bromophenyl)propanoic acidC9H10BrNO2[α]D20=-1.15 (c 1.0, H2O)Source of chirality: kinetic resoluctionAbsolute configuration: (S)

(S)-2-Amino-3-(p-tolyl)propanoic acidC10H13NO2[α]D20=-5.7 (c 1.0, hydrochloric acid)Source of chirality: kinetic resoluctionAbsolute configuration: (S)

(S)-2-Amino-3-(4-nitrophenyl)propanoic acidC9H10N2O4[α]D20=+8.1 (c 1.08, CH3OH)Source of chirality: kinetic resoluctionAbsolute configuration: (S)

(S)-2-Amino-2-phenylacetic acidC8H9NO2[α]D20=+135 (c 0.95, hydrochloric acid)Source of chirality: kinetic resoluctionAbsolute configuration: (S)

(S)-2-Amino-2-(3-(trifluoromethyl)phenyl)acetic acidC9H8F3NO2[α]D25=+11.4 (c 1.05, H2O)Source of chirality: kinetic resoluctionAbsolute configuration: (S)

(S)-2-([1,1′-Biphenyl]-4-yl)-2-aminoacetic acidC14H13NO2[α]D20=+6.9 (c 0.95, CH2Cl2)Source of chirality: kinetic resoluctionAbsolute configuration: (S)

(S)-2-Aminopentanoic acidC5H11NO2[α]D20=+4.6 (c 1.0, H2O)Source of chirality: kinetic resoluctionAbsolute configuration: (S)