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AcisAmide Bond Surrogate Incorporating 1,2,4-Triazole

“…The peptide analogues into which a cis amide bond surrogate has been incorporated are useful for the studies of the active conformation and/or the topology of the active site of original peptides. 1,5-Disubstituted tetrazole is known as a cis amide bond surrogate (Figure 1), 1,2 and it has been incorporated into bradykinin, 3 CCK-B receptor ligands, 4 somatostatin, 5 leucine-enkephalin, 6 and TRH analogues 7 for their biological activity studies. Tetrazole is a good cis amide bond surrogate.…”

Tetrazole peptides as copper(II) ion chelators

“…These peptides exhibit the same receptor activity as morphine, and hence they could be useful as potential natural analgesics [27,28]. The tetrazole ring affects both the conformation of the pep- tides and their interactions with opiate receptors [29]. Therefore, the influence of the cis -amide bond surrogate in metallopeptides was investigated from the chemical and biological points of view.…”

1-Alkyl-5-((di)alkylamino) Tetrazoles: Building Blocks for Peptide Surrogates

“…Tetrazole derivatives have attracted close attention in bioorganic and medicinal chemistry in recent years . The tetrazole moiety is a well-known nonclassical bioisostere for the carboxylate, whereas 1,5-disubstituted tetrazoles are considered as a replacement for the cis -peptide bonds (Figure ) . Tetrazole derivatives were used in the discovery of cephalosporin antibiotics (e.g., Cefoperazone).…”