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

TETRAHEDRON

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Article

Ng-Choi, Iteng¹  Oliveras, Angel¹  Planas, Marta¹  Feliu, Lidia¹ 

[1] Univ Girona, Dept Quim, LIPPSO, Maria Aurelia Capmany 69, Girona 17003, Spain

关键词: Cross-coupling;    Cyclization;    Macrocycles;    Microwave chemistry;    Suzuki-Miyaura;   

DOI  :  10.1016/j.tet.2019.03.014

来源: Elsevier

【 摘 要 】

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. (C) 2019 Elsevier Ltd. All rights reserved.

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