Synthesis and structural study of cyclic 5-aminovaleric acid-linked beta-Ala-beta-Ala dipeptides.
5-Aminovaleric acid and ornithine were evaluated as linkers for the cyclization of beta-dipeptides. Two linked examples of beta-Ala-beta-Ala were prepared by standard coupling methods and their conformations probed by NMR, CD, and computational means. The data suggest that these non- or monosubstituted versions of the target compounds are flexible in solution.
Mengel
Anne
A
Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse. 31, 93053 Regensburg, Germany.
Reiser
Oliver
O
Aubé
Jeffrey
J
D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D021542:Amino Acids, Neutral / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D018716:Molecular Mimicry; D015394:Molecular Structure; D009952:Ornithine / Q000494:pharmacology; D010456:Peptides, Cyclic / Q000737:chemistry*
D021542:Amino Acids, Neutral; D004151:Dipeptides; D010456:Peptides, Cyclic; C002956:alanylalanine; C013809:5-aminovaleric acid; D009952:Ornithine; D000409:Alanine