N-protection of amino acid derivatives catalyzed by immobilized penicillin G acylase

The introduction of a N- alpha -phenylacetyl moiety into glycine, methionine and aspartic acid derivatives using immobilized penicillin G acylase (PGA) as catalyst was studied. High synthetic yields (86-97%) were obtained in biphasic systems under thermodynamic control using fully carboxy-protected...

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Bibliographic Details
Published in:Biocatalysis and biotransformation 1997-01, Vol.14 (4), p.317-332
Main Authors: FITE, M, CAPELLAS, M, DOLORS BENAIGES, M, CAMINAL, G, CLAPES, P, ALVARO, G
Format: Article
Language:English
Subjects:
Amino acids
Binary mixtures
Bioconversions. Hemisynthesis
Biological and medical sciences
Biosynthesis
Biotechnology
Catalysis
Derivatives
Fundamental and applied biological sciences. Psychology
Methods. Procedures. Technologies
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Summary:The introduction of a N- alpha -phenylacetyl moiety into glycine, methionine and aspartic acid derivatives using immobilized penicillin G acylase (PGA) as catalyst was studied. High synthetic yields (86-97%) were obtained in biphasic systems under thermodynamic control using fully carboxy-protected derivatives of amino acids such as H-Gly-OMe, H-Gly-OBzl, H-Met-OEt, H-Asp(OBu super(t))-OMe, H-Asp(OMe)-OMe and H-Asp(OBzl)-OBzl. Moderate yields (50-62%) were obtained for the N- alpha protection of beta -carboxy free, alpha -carboxy esters of aspartic acid such as H-Asp-OMe and H-Asp-OBzl in methanol/buffer mixtures under kinetic control. The synthesis of some phenylacetyl derivatives on a preparative scale under the optimum conditions is also described.
ISSN:1024-2422
1029-2446