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Thia-analogues of amino acids synthesis of peptide derivatives containing 3-thia-analogues of amino acids

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Summary

N-Protected dipeptides containing L-3-thia-analogues of phenylalanine, p-nitro-phenylalanine, lysine and leucine respectively were prepared applying an enantioselective enzymatic reaction step. Racemic synthetic intermediates of the type acyl-NH-CH(R1)-CO-D,L-NH-CH(S-R2)-COOBzl were selectively deprotected at the C-terminus by enzymatic hydrolysis using thermitase or trypsin.

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Abbreviations

Ac:

acetyl

AcOEt:

ethyl acetate

AcOH:

acetic acid

Boc:

tert.-butyloxycarbonyl

Bz:

benzoyl

Bzl:

benzyl

DMF:

dimethyl-formamide

EtOH:

ethanol

THF:

tetrahydrofuran

Z:

benzyloxycarbonyl

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Authors and Affiliations

  1. Institute of Biochemistry, Medical Faculty, Martin-Luther-University, P.O. Box 302, D-O-4010, Halle, Germany

    P. Hermann, H. Baumann, Ch. Herrnstadt & D. Glanz

Authors
  1. P. Hermann
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  2. H. Baumann
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  3. Ch. Herrnstadt
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  4. D. Glanz
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Dedicated to Prof. D. Cavallini at the occasion of his 75th birthday.

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Hermann, P., Baumann, H., Herrnstadt, C. et al. Thia-analogues of amino acids synthesis of peptide derivatives containing 3-thia-analogues of amino acids. Amino Acids 3, 105–118 (1992). https://doi.org/10.1007/BF00806012

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  • DOI: https://doi.org/10.1007/BF00806012

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