Total synthesis of an immunomodulatory phosphoglycolipid from thermophilic bacteria

Hong-Jyune Lin; Avijit Kumar Adak; L Vijaya Raghava Reddy; Shih-Hsiung Wu; Chun-Cheng Lin

doi:10.1002/chem.201204550

Total synthesis of an immunomodulatory phosphoglycolipid from thermophilic bacteria

Chemistry. 2013 Jun 10;19(24):7989-98. doi: 10.1002/chem.201204550. Epub 2013 Apr 17.

Authors

Hong-Jyune Lin¹, Avijit Kumar Adak, L Vijaya Raghava Reddy, Shih-Hsiung Wu, Chun-Cheng Lin

Affiliation

¹ Department of Chemistry, National Tsing Hua University, No. 101, Section 2, Kuang Fu Road, Hsinchu 300, Taiwan.

PMID: 23595956
DOI: 10.1002/chem.201204550

Abstract

A method for the stereocontrolled synthesis of a bacterial phosphoglycolipid (PGL1) isolated from thermophilic bacteria is described. The key features of the synthesis include a highly α-selective glycosylation reaction between a trichloroacetimidate donor and a D-lyxose-derived primary alcohol acceptor and the late-stage incorporation of the phospholipid.

Publication types

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

MeSH terms

Acetamides / chemistry*
Adjuvants, Immunologic / chemical synthesis*
Adjuvants, Immunologic / chemistry
Adjuvants, Immunologic / pharmacology
Chloroacetates / chemistry*
Glycosylation
Molecular Structure
Pentoses / chemistry*
Phospholipids / chemical synthesis*
Phospholipids / chemistry
Phospholipids / pharmacology
Silanes / chemistry
Thermus / chemistry*

Substances

Acetamides
Adjuvants, Immunologic
Chloroacetates
Pentoses
Phospholipids
Silanes
lyxose
trichloroacetamide