Visible-Light-Induced Copper-Catalyzed Asymmetric C(sp3)-C(sp3)-H Glycosylation: Access to C-Glycopeptides

Ya-Nan Ding; Ning Li; Yan-Chong Huang; Yang An; Yong-Min Liang

doi:10.1021/acs.orglett.2c01501

Visible-Light-Induced Copper-Catalyzed Asymmetric C(sp³)-C(sp³)-H Glycosylation: Access to C-Glycopeptides

Org Lett. 2022 Jul 1;24(25):4519-4523. doi: 10.1021/acs.orglett.2c01501. Epub 2022 Jun 21.

Authors

Ya-Nan Ding¹, Ning Li¹, Yan-Chong Huang¹, Yang An¹, Yong-Min Liang¹

Affiliation

¹ State Key Laboratory of Applied Organic Chemistry, School of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P.R. China.

PMID: 35729799
DOI: 10.1021/acs.orglett.2c01501

Abstract

Herein, a practical and highly efficient method for visible-light-induced copper-catalyzed N-aminoquinoline-directed asymmetric C(sp³)-C(sp³)-H glycosylation was reported. At the same time, C(sp³)-C(sp³)-H glycosylation of nondeoxysugars with amino acids to construct C-glycopeptides was achieved. This approach promoted the synthesis of various C-glycopeptides and provided a new model for the synthesis of C-glycoamino acids.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemistry
Catalysis
Copper* / chemistry
Glycopeptides* / chemistry
Glycosylation

Substances

Amino Acids
Glycopeptides
Copper