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 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.
Wünsch
E
E
Max-Planck-Institute for Biochemistry, Martinsried, Federal Republic of Germany.
Stocker
H
H
Malon
P
P
Gut
V
V
Cerovský
V
V
Zertová
M
M
Laffan
D D
DD
D000600:Amino Acids, Dicarboxylic / Q000138:chemical synthesis; D002116:Calcitonin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D010452:Peptide Biosynthesis; D010455:Peptides / Q000138:chemical synthesis; D013696:Temperature
D000600:Amino Acids, Dicarboxylic; D010455:Peptides; C019146:2-aminosuberic acid; D002116:Calcitonin