Resolution of N-protected amino acid esters using whole cells of Candida parapsilosis ATCC 7330

Whole cells of Candida parapsilosis ATCC 7330 were used for the resolution of N-acetyl amino acid esters. Excellent enantioselectivities (E = 40 to >500) were achieved for the resolution of N-protected protein and non-protein amino acid esters giving good yields (28–50%) and high enantiomeric excesses (up to >99%) for both enantiomers.

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(R)-Ethyl 2-acetamido-3-phenylpropanoateC13H17NO3Ee >99%[α]D34=-12.4 (c 1, EtOH)Source of chirality: resolutionAbsolute configuration: (R)

(S)-2-Acetamido-3-phenylpropanoic acidC11H13NO3Ee 87%[α]D35=+28.9 (c 1, MeOH)Source of chirality: resolutionAbsolute configuration: (S)

(R)-Ethyl 2-acetamido-3-(4-fluorophenyl)propanoateC13H16FNO3Ee 99%[α]D30=-72.5 (c 2, CHCl3)Source of chirality: resolutionAbsolute configuration: (R)

(S)-2-Acetamido-3-(4-fluorophenyl)propanoic acidC11H12FNO3Ee 98%[α]D30=+30.8 (c 1, MeOH)Source of chirality: resolutionAbsolute configuration: (S)

(R)-Ethyl 2-acetamido-3-(4-chlorophenyl)propanoateC13H16ClNO3Ee >99%[α]D34=-16.8 (c 2, EtOH)Source of chirality: resolutionAbsolute configuration: (R)

(S)-2-Acetamido-3-(4-chlorophenyl)propanoic acidC11H12ClNO3Ee 99%[α]D35=+47.5 (c 1, MeOH)Source of chirality: resolutionAbsolute configuration: (S)

(R)-Ethyl 2-acetamido-3-(4-bromophenyl)propanoateC13H16BrNO3Ee >99%[α]D34=-17.5 (c 1, EtOH)Source of chirality: resolutionAbsolute configuration: (R)

(S)-2-Acetamido-3-(4-bromophenyl)propanoic acidC11H12BrNO3Ee 98%[α]D30=+35.5 (c 1, MeOH)Source of chirality: resolutionAbsolute configuration: (S)

(R)-Ethyl 2-acetamido-4-phenylbutanoateC14H19NO3Ee 94%[α]D30=-1.8 (c 2, EtOH)Source of chirality: resolutionAbsolute configuration: (R)

(S)-2-Acetamido-4-phenylbutanoic acidC12H15NO3Ee 98%[α]D35=+14.6 (c 2, MeOH)Source of chirality: resolutionAbsolute configuration: (S)

(R)-Ethyl 2-acetamido-3-(1H-indol-3-yl)propanoateC15H18N2O3Ee >99%[α]D30=-38.7 (c 1, CHCl3)Source of chirality: resolutionAbsolute configuration: (R)

(S)-2-Acetamido-3-(1H-indol-3-yl)propanoic acidC13H14N2O3Ee 70%[α]D35=+18.8 (c 0.5, aq NaOH)Source of chirality: resolutionAbsolute configuration: (S)

(R)-Ethyl 2-acetamido-3-(4-hydroxyphenyl)propanoateC13H17NO4Ee 95%[α]D34=-16.2 (c 2, EtOH)Source of chirality: resolutionAbsolute configuration: (R)

(S)-2-Acetamido-3-(4-hydroxyphenyl)propanoic acidC11H13NO4Ee 99%[α]D30=+44.9 (c 0.5, MeOH)Source of chirality: resolutionAbsolute configuration: (S)

(R)-Ethyl 2-acetamido-2-phenylacetateC12H15NO3Ee 36%[α]D34=-48.6 (c 2, EtOH)Source of chirality: resolutionAbsolute configuration: (R)