Synthesis and antiviral evaluation of 6'-acylamido-6'-deoxy-α-D-mannoglycerolipids

Jun Zhang; Yihua Sun; Wei Wang; Xiaoshuang Zhang; Chunxia Li; Huashi Guan

doi:10.1016/j.carres.2013.08.010

Synthesis and antiviral evaluation of 6'-acylamido-6'-deoxy-α-D-mannoglycerolipids

Carbohydr Res. 2013 Nov 15:381:74-82. doi: 10.1016/j.carres.2013.08.010. Epub 2013 Aug 23.

Authors

Jun Zhang¹, Yihua Sun, Wei Wang, Xiaoshuang Zhang, Chunxia Li, Huashi Guan

Affiliation

¹ Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, PR China.

PMID: 24076433
DOI: 10.1016/j.carres.2013.08.010

Abstract

Eight new aminomannoglycerolipids (2a-h) with linear, branched, or aromatic acyl chains were synthesized and evaluated for their anti-influenza A virus (IAV) activity. By comparing six mannosyl donors with different protecting and leaving groups, the critical glycosylation reaction employed mannosyl trichloroacetimidate with 2-O-benzoyl protecting group as the donor to give the glycoside with absolute α-anomeric selectivity. The bioactivity results showed that the branched compound 2g could effectively inhibit IAV multiplication in MDCK cells with IC50 69.9μM.

Keywords: Aminoglycoglycerolipid; Glycosylation; Influenza A virus; α-Anomeric selectivity.

Publication types

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

MeSH terms

Animals
Antiviral Agents / chemical synthesis
Antiviral Agents / chemistry
Antiviral Agents / pharmacology*
Carbohydrate Conformation
Cells
Dogs
Dose-Response Relationship, Drug
Glycolipids / chemical synthesis
Glycolipids / chemistry
Glycolipids / pharmacology*
Influenza A virus / drug effects*
Madin Darby Canine Kidney Cells / drug effects
Madin Darby Canine Kidney Cells / virology
Microbial Sensitivity Tests
Structure-Activity Relationship

Substances

Antiviral Agents
Glycolipids