The backbone N-(4-azidobutyl) linker for the preparation of peptide chimera

Ana I. Fernández-Llamazares; Jesús García; Jaume Adan; David Meunier; Francesc Mitjans; Jan Spengler; Fernando Albericio

doi:10.1021/ol402150m

The backbone N-(4-azidobutyl) linker for the preparation of peptide chimera

Ana I. Fernández-Llamazares
, Jesús García
, Jaume Adan
, David Meunier
, Francesc Mitjans
, Jan Spengler
, Fernando Albericio

Institute for Research in Biomedicine
Biomaterials and Nanomedicine
Centro Tecnologico Leitat
University of Barcelona
University of KwaZulu-Natal

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

A robust synthetic strategy for the introduction of the N-(4-azidobutyl) linker into peptides using standard SPPS techniques is described. Based on the example of Cilengitide it is shown that the N-(4-azidobutyl) group exerts similar conformational restraints as a backbone N-Me group and allows conjugation of a desired molecule either via click chemistry or - after azide reduction - via acylation or reductive alkylation.

Original language	English
Pages (from-to)	4572-4575
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	17
DOIs	https://doi.org/10.1021/ol402150m
State	Published - 6 Sep 2013
Externally published	Yes

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10.1021/ol402150m

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abstract = "A robust synthetic strategy for the introduction of the N-(4-azidobutyl) linker into peptides using standard SPPS techniques is described. Based on the example of Cilengitide it is shown that the N-(4-azidobutyl) group exerts similar conformational restraints as a backbone N-Me group and allows conjugation of a desired molecule either via click chemistry or - after azide reduction - via acylation or reductive alkylation.",

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AU - Fernández-Llamazares, Ana I.

AU - García, Jesús

AU - Adan, Jaume

AU - Meunier, David

AU - Mitjans, Francesc

AU - Spengler, Jan

AU - Albericio, Fernando

PY - 2013/9/6

Y1 - 2013/9/6

N2 - A robust synthetic strategy for the introduction of the N-(4-azidobutyl) linker into peptides using standard SPPS techniques is described. Based on the example of Cilengitide it is shown that the N-(4-azidobutyl) group exerts similar conformational restraints as a backbone N-Me group and allows conjugation of a desired molecule either via click chemistry or - after azide reduction - via acylation or reductive alkylation.

AB - A robust synthetic strategy for the introduction of the N-(4-azidobutyl) linker into peptides using standard SPPS techniques is described. Based on the example of Cilengitide it is shown that the N-(4-azidobutyl) group exerts similar conformational restraints as a backbone N-Me group and allows conjugation of a desired molecule either via click chemistry or - after azide reduction - via acylation or reductive alkylation.

UR - https://www.scopus.com/pages/publications/84883787871

U2 - 10.1021/ol402150m

DO - 10.1021/ol402150m

M3 - Artículo

C2 - 24006938

AN - SCOPUS:84883787871

SN - 1523-7060

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JO - Organic Letters

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ER -

The backbone N-(4-azidobutyl) linker for the preparation of peptide chimera

Abstract

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