The peptides of alpha-aminosuberic acid I. New intermediates for synthetic studies

The paper describes the synthesis of alpha-aminosuberic acid derivatives suitable for the synthesis of peptides. These include Z-, Boc- and Fmoc-protection on the alpha-amino group, benzyl ester, Boc-hydrazide and Z-hydrazide as well as the free carboxylic function in the side chain, and methyl este...

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Bibliographic Details
Published in:Amino acids 2000-01, Vol.18 (3), p.219-227
Main Authors: Wünsch, E, Stocker, H, Malon, P, Gut, V, Cerovský, V, Zertová, M, Laffan, D D
Format: Article
Language:English
Subjects:
Amino Acids, Dicarboxylic - chemical synthesis
Calcitonin - analogs & derivatives
Calcitonin - chemical synthesis
Intermediates
Optical activity
Peptide Biosynthesis
Peptides
Peptides - chemical synthesis
Temperature
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Summary:The paper describes the synthesis of alpha-aminosuberic acid derivatives suitable for the synthesis of peptides. These include Z-, Boc- and Fmoc-protection on the alpha-amino group, benzyl ester, Boc-hydrazide and Z-hydrazide as well as the free carboxylic function in the side chain, and methyl ester, benzyl ester or free alpha-carboxylic group. Their use is demonstrated on the synthesis of the respective derivatives of Asu-Val-Leu. The enzyme catalyzed reaction was successfully used both as a route to L-Asu from the D,L-compound as well as for the direct synthesis of the optically active tripeptide derivative from the Z-D,L-Asu-OH.
ISSN:0939-4451
1438-2199
DOI:10.1007/s007260050019