Diversity-Oriented Peptide Stapling: A Third Generation Copper-Catalysed Azide-Alkyne Cycloaddition Stapling and Functionalisation Strategy

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00475168" target="_blank" >RIV/61388963:_____/17:00475168 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1002/chem.201700128" target="_blank" >http://dx.doi.org/10.1002/chem.201700128</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/chem.201700128" target="_blank" >10.1002/chem.201700128</a>

Result language

angličtina

Original language name

Diversity-Oriented Peptide Stapling: A Third Generation Copper-Catalysed Azide-Alkyne Cycloaddition Stapling and Functionalisation Strategy

Original language description

The introduction of macrocyclic constraints in peptides (peptide stapling) is an important tool within peptide medicinal chemistry for stabilising and pre-organising peptides in a desired conformation. In recent years, the copper-catalysed azide-alkyne cycloaddition (CuAAC) has emerged as a powerful method for peptide stapling. However, to date CuAAC stapling has not provided a simple method for obtaining peptides that are easily diversified further. In the present study, we report a new diversity-oriented peptide stapling ( DOPS) methodology based on CuAAC chemistry. Stapling of peptides incorporating two azidemodified amino acids with 1,3,5-triethynylbenzene efficiently provides (i, i+7)- and ( i, i+9)- stapled peptides with a single free alkyne positioned on the staple, which can be further conjugated or dimerised. A unique feature of the present method is that it provides easy access to radiolabelled stapled peptides by catalytic tritiation of the alkyne positioned on the staple.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

—

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2017

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Chemistry - A European Journal

ISSN

0947-6539

e-ISSN

—

Volume of the periodical

23

Issue of the periodical within the volume

14

Country of publishing house

DE - GERMANY

Number of pages

6

Pages from-to

3490-3495

UT code for WoS article

000395775700032

EID of the result in the Scopus database

2-s2.0-85013249260