The impacts of benzoyl and benzyl groups on the non-covalent interactions and electronic properties of glycosyl acceptors

Abstract

Modulating the reactivity of glycosyl acceptors has become a key in promoting the chemical synthesis of complex glycans. Herein, computational chemistry was employed to explore the impacts of protecting groups on the non-covalent interactions and electronic properties of glycosyl acceptors. Wavefunction analyses showed that substituting benzoyl groups with benzyl groups and introducing a benzyl group to the C2 amine of a D-GlcpNAc residue can eliminate intra-/intermolecular hydrogen bonds, thereby altering the charge distribution significantly. This protecting group-induced charge distribution increases the nucleophilicity of hydroxyl group. This study may contribute to understanding the assistance of computational chemistry in glycan synthesis.

Keywords:

• Computational quantum chemistry
• DFT calculations
• glycosylation reactivity
• glycosyl acceptor
• protecting group

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

The authors are grateful to the National Key R&D Program of China [2020YFA0908304], the National Natural Science Foundation of China [22325803, 22277042, 22077052, 22177041] and the Project of Taihu Talent Plan.