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Aza-Amino Acid Scan for Rapid Identification of Secondary Structure Based on the Application of N -Boc-Aza 1 -Dipeptides in Peptide Synthesis

2004; American Chemical Society; Volume: 126; Issue: 21 Linguagem: Inglês

10.1021/ja039643f

1943-2984

Rosa E. Meléndez, William D. Lubell,

Neuropeptides and Animal Physiology

Azapeptides, peptide analogues in which the α-carbon of one or more of the amino acid residues is replaced with a nitrogen atom, exhibit propensity for adopting β-turn conformations. A general protocol for the synthesis of azapeptides without racemization on solid phase has now been developed by introducing the aza-amino acid residue as an N-Boc-aza1-dipeptide. This approach has been validated by the synthesis of six N-Boc-aza1-dipeptides and their subsequent introduction into analogues of the C-terminal peptide fragment of the human calcitonin gene-related peptide (hCGRP). By performing an aza-amino acid scan of such antagonist peptides, a set of aza-hCGRP analogues was synthesized to examine the relationship between turn secondary structure and biological activity.