3-Azido-aspartic acid derivatives - orthogonally protected precursors for the stereoselective incorporation of 2,3-diaminosuccinic acid into peptide structures.
The stereoselective synthesis of orthogonally protected 3-azido aspartic acid derivatives is described. The convenience of their application as 2,3-diaminosuccinic acid in peptide chemistry was demonstrated by the incorporation of the nonproteinogenic diamino diacid as a cystine-substitute into the core structure of somatostatin.
Riemer
C
C
Institut für Organische Chemie und Biochemie, Technische Universität München, Lichtenbergstrasse 4, D-85747 Garching, Germany.
Bayer
T
T
Schmitt
H
H
Kessler
H
H
D000599:Amino Acids, Diamino / Q000737:chemistry*; D001224:Aspartic Acid / Q000031:analogs & derivatives*; D001386:Azides / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013004:Somatostatin / Q000031:analogs & derivatives / Q000138:chemical synthesis; D013237:Stereoisomerism
D000599:Amino Acids, Diamino; D001386:Azides; D010456:Peptides, Cyclic; D001224:Aspartic Acid; D013004:Somatostatin; C031934:diaminosuccinic acid