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


    Cao, Benjamin and Chen, Xingqiang and Yamaryo-Botte, Yoshiki and Richardson, Mark B and Martin, Kirstee L and Khairallah, George N and Rupasinghe, Thusita W T and O'Flaherty, Roisin and O'Hair, Richard A J and Ralton, Julie E and Crellin, Paul K and Coppel, Ross L and McConville, Malcolm J and Williams, Spencer J (2013) Synthesis, Structural Elucidation, And Biochemical Analysis of Immunoactive Glucuronosyl Diacylglycerides of Mycobacteria and Corynebacteria. Journal of Organic Chemistry, 78 (6). pp. 2175-2190. ISSN 0022-3263

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    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) GlcAGroAc2 glycolipids from M. smegmatis and Corynebacterium glutamicum. A synthetic hydrophobic octyl glucuronoside was used to characterize the GDP-mannose-dependent mannosyltransferase MgtA from C. glutamicum that extends GlcAGroAc2. This enzyme is an Mg2+/Mn2+-dependent metalloenzyme that undergoes dramatic activation upon reduction with dithiothreitol.

    Item Type: Article
    Keywords: Synthesis; Structural Elucidation; Biochemical; Analysis; Immunoactive; Glucuronosyl; Diacylglycerides; Mycobacteria; Corynebacteria;
    Academic Unit: Faculty of Science and Engineering > Chemistry
    Item ID: 15033
    Identification Number: https://doi.org/10.1021/jo302508e
    Depositing User: Roisin O'Flaherty
    Date Deposited: 16 Nov 2021 15:31
    Journal or Publication Title: Journal of Organic Chemistry
    Publisher: American Chemical Society
    Refereed: Yes
    URI:

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