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  • Title: Benzotriazole-mediated synthesis of aza-peptides: en route to an aza-leuenkephalin analogue.
    Author: Abo-Dya NE, Biswas S, Basak A, Avan I, Alamry KA, Katritzky AR.
    Journal: J Org Chem; 2013 Apr 19; 78(8):3541-52. PubMed ID: 23373789.
    Abstract:
    Novel N-(N-Pg-azadipeptidoyl)benzotriazoles 20a-e couple efficiently with α-amino acids 21a-e, dipeptides 22a-c, aminoxyacetic acid 23a, depsidipeptide 23b, and α-hydroxy-β-phenylpropionic acid 27 yielding, respectively, azatripeptides 24a-g, azatetrapeptides 25a,b, a hybrid azatripeptide with an oxyamide bond 26a, a hybrid azatetrapeptide with an ester bond 26b, and a hybrid azatripeptide with an ester bond 28. A new protocol for the synthesis of N-Pg-azatripeptides 33a,b and 35a,b, each containing a natural amino acid at the N-terminus, avoids the low coupling rates of the aza-amino acid residue and enables the solution-phase synthesis of an azaphenylalanine analogue of Leu-enkephalin 40.
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