Visible-Light-Promoted Stereoselective C(sp3)-H Glycosylation for the Synthesis of C-Glycoamino Acids and C-Glycopeptides

被引：75

作者：

Qi, Rupeng ^{[1
]}

Wang, Chao ^{[1
]}

Ma, Zijian ^{[1
]}

Wang, Hongying ^{[1
]}

Chen, Qiao ^{[2
]}

Liu, Liangyu ^{[2
]}

Pan, Da ^{[2
]}

Ren, Xiaoyu ^{[1
]}

Wang, Rui ^{[1
,3
]}

Xu, Zhaoqing ^{[1
,3
]}

机构：

[1] Lanzhou Univ, Sch Basic Med Sci, Key Lab Preclin Study New Drugs Gansu Prov, 199 West Donggang Rd, Lanzhou 730000, Peoples R China

[2] Lanzhou Univ, Sch Pharm, 199 West Donggang Rd, Lanzhou 730000, Peoples R China

[3] Chinese Acad Med Sci, Res Unit Peptide Sci, 2019RU066, 199 West Donggang Rd, Lanzhou 730000, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 24期

基金：

中国国家自然科学基金;

关键词：

C(sp(3))-H) Glycosylation; Diastereoselectivity; Glycoamino Acids; Glycopeptides; Photocatalysis; GLYCOSIDE ANALOG; BIOAVAILABILITY; DEPROTONATION; CARBOHYDRATE; PEPTIDES; STRATEGY;

D O I：

10.1002/anie.202200822

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The glycosylative modification of peptides could improve the pharmacological properties of peptide drugs and deliver them efficiently to the target sites. Compared with O-/N-glycosides, C-glycosides exhibit more metabolic stability. We here disclose the first example of visible-light-promoted and Cu-catalyzed stereoselective C-glycosylation. The mild reaction conditions are compatible with various carbohydrate substrates, as demonstrated with a series of monosaccharides and a disaccharide, and are amenable to the synthesis of a wide variety of C-glycoamino acids and C-glycopeptidomimetics with good yields and excellent stereoselectivities. The dual-functional photocatalyst formed in situ via coordination of the glycine derivative and the chiral phosphine Cu complex could not only catalyze the photoredox process but also control the stereoselectivity of the glycosylation reaction.

引用

页数：5

共 57 条

[41] 1,2-trans-Stereoselective Synthesis of C-Glycosides of 2-Deoxy-2-amino-sugars Involving Glycosyl Radicals [J].