Unknown

Dataset Information

0

Structural elucidation of diglycosyl diacylglycerol and monoglycosyl diacylglycerol from Streptococcus pneumoniae by multiple-stage linear ion-trap mass spectrometry with electrospray ionization.


ABSTRACT: 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 ?-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.

SUBMITTER: Tatituri RV 

PROVIDER: S-EPMC3712276 | BioStudies | 2012-01-01

REPOSITORIES: biostudies

Similar Datasets

2007-01-01 | S-EPMC2747347 | BioStudies
2020-01-01 | S-EPMC6949391 | BioStudies
2003-01-01 | S-EPMC164687 | BioStudies
1985-01-01 | S-EPMC1152861 | BioStudies
1990-01-01 | S-EPMC1131126 | BioStudies
2017-01-01 | S-EPMC5282945 | BioStudies
2019-01-01 | S-EPMC6338697 | BioStudies
2013-01-01 | S-EPMC3733143 | BioStudies
2010-01-01 | S-EPMC2847672 | BioStudies
2014-01-01 | S-EPMC4255645 | BioStudies