Journal article

Synthesis, Structural Elucidation, And Biochemical Analysis of Immunoactive Glucuronosyl Diacylglycerides of Mycobacteria and Corynebacteria

Benjamin Cao, Xingqiang Chen, Yoshiki Yamaryo-Botte, Mark B Richardson, Kirstee L Martin, George N Khairallah, Thusita WT Rupasinghe, Roisin M O'Flaherty, Richard AJ O'Hair, Julie E Ralton, Paul K Crellin, Ross L Coppel, Malcolm J McConville, Spencer J Williams

JOURNAL OF ORGANIC CHEMISTRY | AMER CHEMICAL SOC | Published : 2013

Abstract

Glucuronosyl diacylglycerides (GlcAGroAc2) are functionally important glycolipids and membrane anchors for cell wall lipoglycans in the Corynebacteria. Here we describe the complete synthesis of distinct acyl-isoforms of GlcAGroAc2 bearing both acylation patterns of (R)-tuberculostearic acid (C19:0) and palmitic acid (C16:0) and their mass spectral characterization. Collision-induced fragmentation mass spectrometry identified characteristic fragment ions that were used to develop "rules" allowing the assignment of the acylation pattern as C19:0 (sn-1), C16:0 (sn-2) in the natural product from Mycobacterium smegmatis, and the structural assignment of related C18:1 (sn-1), C16:0 (sn-2) GlcAGro..

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