| Synthesis, structural elucidation and biochemical analysis of immunoactive glucuronosyl diacylglycerides of Mycobacteria and Corynebacteria. | |
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MedLine Citation:
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PMID: 23343519 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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. |
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Authors:
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Benjamin Cao; Xing Qiang Chen; Yoshiki Yamaryo-Botte; Mark Richardson; Kirstee Martin; George N Khairallah; Thusita W T Rupasinghe; Roisin M O'Flaherty; Richard A J O'Hair; Julie E Ralton; Paul K Crellin; Ross L Coppel; Malcolm J McConville; Spencer John Williams |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2013-1-23 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2013 Jan |
Date Detail:
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Created Date: 2013-1-24 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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