Document Detail


Structural elucidation of diglycosyl diacylglycerol and monoglycosyl diacylglycerol from Streptococcus pneumoniae by multiple-stage linear ion-trap mass spectrometry with electrospray ionization.
MedLine Citation:
PMID:  22282097     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The cell wall of the pathogenic bacterium Streptococcus pneumoniae contains glucopyranosyl diacylglycerol (GlcDAG) and galactoglucopyranosyldiacylglycerol (GalGlcDAG). The specific GlcDAG consisting of vaccenic acid substituent at sn-2 was recently identified as another glycolipid antigen family recognized by invariant natural killer T-cells. Here, we describe a linear ion-trap multiple-stage (MS(n) ) mass spectrometric approach towards structural analysis of GalGlcDAG and GlcDAG. Structural information derived from MS(n) (n = 2, 3) on the [M + Li](+) adduct ions desorbed by electrospray ionization affords identification of the fatty acid substituents, assignment of the fatty acyl groups on the glycerol backbone, as well as the location of double bond along the fatty acyl chain. The identification of the fatty acyl groups and determination of their regio-specificity were confirmed by MS(n) (n = 2, 3) on the [M + NH(4) ](+) ions. We establish the structures of GalGlcDAG and GlcDAG isolated from S. pneumoniae, in which the major species consists of a 16:1- or 18:1-fatty acid substituent mainly at sn-2, and the double bond of the fatty acid is located at ω-7 (n-7). More than one isomers were found for each mass in the family. This mass spectrometric approach provides a simple method to achieve structure identification of this important lipid family that would be very difficult to define using the traditional method.
Authors:
Raju Venkata Veera Tatituri; Michael B Brenner; John Turk; Fong-Fu Hsu
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural    
Journal Detail:
Title:  Journal of mass spectrometry : JMS     Volume:  47     ISSN:  1096-9888     ISO Abbreviation:  J Mass Spectrom     Publication Date:  2012 Jan 
Date Detail:
Created Date:  2012-01-27     Completed Date:  2012-03-21     Revised Date:  2013-12-18    
Medline Journal Info:
Nlm Unique ID:  9504818     Medline TA:  J Mass Spectrom     Country:  England    
Other Details:
Languages:  eng     Pagination:  115-23     Citation Subset:  IM    
Copyright Information:
Copyright © 2012 John Wiley & Sons, Ltd.
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MeSH Terms
Descriptor/Qualifier:
Deuterium Exchange Measurement
Glycolipids / chemistry*
Spectrometry, Mass, Electrospray Ionization / methods*
Streptococcus pneumoniae / chemistry*
Grant Support
ID/Acronym/Agency:
P30 DK020579/DK/NIDDK NIH HHS; P30 DK056341/DK/NIDDK NIH HHS; P30-DK-56341/DK/NIDDK NIH HHS; P41 RR000954/RR/NCRR NIH HHS; P41-RR-00954/RR/NCRR NIH HHS; P60 DK020579/DK/NIDDK NIH HHS; P60-DK-20579/DK/NIDDK NIH HHS; R01AI063428-06A1/AI/NIAID NIH HHS; R37-DK-34388/DK/NIDDK NIH HHS
Chemical
Reg. No./Substance:
0/1,2-diacyl-3-O-(2-amino-2-deoxy-glucopyranose-(1-4)-O-induronopyranuronic acid)-glycerol; 0/Glycolipids
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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