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Solid-phase synthesis of biaryl cyclic peptides containing a histidine-tyrosine linkage

Author:
Ng-Choi, Iteng, Oliveras, Àngel, Planas, Marta, Feliu, Lidia
Source:
Tetrahedron 2019 v.75 no.18 pp. 2625-2636
ISSN:
0040-4020
Subject:
Suzuki reaction, chemical structure, cyclic peptides, histidine, macrocyclization reactions, microwave treatment
Abstract:
A solid-phase strategy for the synthesis of biaryl cyclic peptides containing a side-chain to side-chain His-Tyr linkage was developed. The key step was the macrocyclization of a linear peptidyl resin incorporating a 5-bromohistidine and a 3-boronotyrosine via the formation of the biaryl bond by means of a microwave-assisted Suzuki-Miyaura reaction. This method allowed direct access to biaryl cyclic peptides containing a 3- or 5-amino acid ring and bearing the histidine residue at the N- or the C-terminus, being especially conducive for analogues in which this amino acid is located at the C-terminus. This study also served to establish a strategy for the synthesis of biaryl cyclic peptides derived from the two hemispheres of the natural biaryl bicyclic peptides aciculitins.
Agid:
6335347