Diastereoselective Anomeric C(sp3)−H Cyclization Towards the Design of New Cyclophane-Braced Glycopeptides

Sakna Bazzi; Ameni Hadj Mohamed; Dmytro Ryzhakov; Juba Ghouilem; Mehdi A. Beniddir; Vincent Gandon; Samir Messaoudi

doi:10.1002/anie.202418057

Diastereoselective Anomeric C(sp³)−H Cyclization Towards the Design of New Cyclophane-Braced Glycopeptides

Sakna Bazzi
, Ameni Hadj Mohamed
, Dmytro Ryzhakov
, Juba Ghouilem
, Mehdi A. Beniddir
, Vincent Gandon
, Samir Messaoudi

Université Paris-Saclay
Centre national de la recherche scientifique
Institut de Chimie Moléculaire et des Matériaux d'Orsay

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

6 Citations (Scopus)

Abstract

Here we report a macrocyclization route towards the synthesis of glycophane peptides by a selective C−H arylation of the anomeric bond. This approach demonstrates the power of Pd-catalysis C−H activation to access unusual cyclic peptides.

Original language	English
Article number	e202418057
Journal	Angewandte Chemie - International Edition
Volume	64
Issue number	6
DOIs	https://doi.org/10.1002/anie.202418057
Publication status	Published - 3 Feb 2025

Keywords

Cyclic glycopeptides
C−H activation
Glycosides
Palladium
Peptides

Access to Document

10.1002/anie.202418057

Cite this

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title = "Diastereoselective Anomeric C(sp3)−H Cyclization Towards the Design of New Cyclophane-Braced Glycopeptides",

abstract = "Here we report a macrocyclization route towards the synthesis of glycophane peptides by a selective C−H arylation of the anomeric bond. This approach demonstrates the power of Pd-catalysis C−H activation to access unusual cyclic peptides.",

keywords = "Cyclic glycopeptides, C−H activation, Glycosides, Palladium, Peptides",

author = "Sakna Bazzi and \{Hadj Mohamed\}, Ameni and Dmytro Ryzhakov and Juba Ghouilem and Beniddir, \{Mehdi A.\} and Vincent Gandon and Samir Messaoudi",

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AU - Bazzi, Sakna

AU - Hadj Mohamed, Ameni

AU - Ryzhakov, Dmytro

AU - Ghouilem, Juba

AU - Beniddir, Mehdi A.

AU - Gandon, Vincent

AU - Messaoudi, Samir

PY - 2025/2/3

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AB - Here we report a macrocyclization route towards the synthesis of glycophane peptides by a selective C−H arylation of the anomeric bond. This approach demonstrates the power of Pd-catalysis C−H activation to access unusual cyclic peptides.

KW - Cyclic glycopeptides

KW - C−H activation

KW - Glycosides

KW - Palladium

KW - Peptides

U2 - 10.1002/anie.202418057

DO - 10.1002/anie.202418057

M3 - Article

AN - SCOPUS:85210511642

SN - 1433-7851

VL - 64

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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