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

Angew Chem Int Ed Engl. 2024 Nov 8:e202418057. doi: 10.1002/anie.202418057. Online ahead of print.

Authors

Sakna Bazzi¹, Ameni Hadj Mohamed^{1

2}, Dmytro Ryzhakov¹, Juba Ghouilem¹, Mehdi A Beniddir¹, Vincent Gandon³, Samir Messaoudi^{1

2}

Affiliations

¹ Université Paris-Saclay, CNRS, BioCIS, 91400, Orsay, France.
² Laboratoire de Synthèse Organique, Ecole Polytechnique, CNRS, ENSTA, Institut Polytechnique de Paris, Palaiseau, France.
³ Université Paris-Saclay, CNRS, ICMMO, 91400, Orsay, France.

PMID: 39513488
DOI: 10.1002/anie.202418057

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.