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

Producción científica: Contribución a una revista › Artículo › revisión exhaustiva

9 Citas (Scopus)

Resumen

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.

Idioma original	Inglés
Páginas (desde-hasta)	4572-4575
Número de páginas	4
Publicación	Organic Letters
Volumen	15
N.º	17
DOI	https://doi.org/10.1021/ol402150m
Estado	Publicada - 6 sep. 2013
Publicado de forma externa	Sí

Acceder al documento

10.1021/ol402150m

Otros archivos y enlaces

Enlace a la publicación en Scopus

Citar esto

@article{70bd294cb1354897964d65845955d56b,

title = "The backbone N-(4-azidobutyl) linker for the preparation of peptide chimera",

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.",

author = "Fern{\'a}ndez-Llamazares, \{Ana I.\} and Jes{\'u}s Garc{\'i}a and Jaume Adan and David Meunier and Francesc Mitjans and Jan Spengler and Fernando Albericio",

year = "2013",

month = sep,

day = "6",

doi = "10.1021/ol402150m",

language = "Ingl{\'e}s",

volume = "15",

pages = "4572--4575",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - The backbone N-(4-azidobutyl) linker for the preparation of peptide chimera

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

VL - 15

SP - 4572

EP - 4575

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

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

Resumen

Acceder al documento

Otros archivos y enlaces

Huella

Citar esto