| Characterization of mycolic acids from the pathogen Rhodococcus equi by tandem mass spectrometry with electrospray ionization. | |
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MedLine Citation:
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PMID: 20946862 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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We describe a simple tandem mass spectrometric approach toward structural characterization of mycolic acids, the long-chain α-alkyl-β-hydroxy fatty acids unique to mycobacteria and related taxa. On collisionally activated dissociation in a linear ion trap or tandem quadrupole mass spectrometer, the [M-H](-) ions of mycolic acid generated by electrospray ionization undergo dissociation to eliminate the meroaldehyde residue, leading to formation of carboxylate anions containing α-alkyl chains. The structural information from these fragment ions affords structural assignment of the mycolic acids, including the lengths of the meromycolate chain and the α-branch. This study revealed that the mycolic acids isolated from pathogenic Rhodococcus equi 103 contained a series of homologous ions having C(30) to C(50) chain with 0-2 double bonds. The α-branch ranged from C(10) to C(18) with 0 to 1 double bond, in which 16:0 and 14:0 are the most prominent, whereas the meromycolate chain ranged from C(14) to C(34) with 0 to 2 double bonds. The major molecular species consisted of more than 3 isomers that differ by the lengths of the α-branch or meromycolate chain, and up to 10 isobaric isomers were identified for some minor ions. We also employed tandem quadrupole mass spectrometry with precursor ion and neutral loss scans for profiling mycolic acid with specific structure in mixtures. The tandem spectra obtained from precursor ion scans of m/z 255 (16:0-carboxylate anion) and m/z 227 (14:0-carboxylate anion) may provide a simple specific means for classification of Rhodococci species, whereas tandem spectra from neutral loss of meroaldehyde residue scans provided a simple approach to reveal the mycolic acid molecules with specific meromycolate chain in mixtures. |
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Authors:
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Fong-Fu Hsu; Kristina Soehl; John Turk; Albert Haas |
Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't Date: 2010-10-12 |
Journal Detail:
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Title: Analytical biochemistry Volume: 409 ISSN: 1096-0309 ISO Abbreviation: Anal. Biochem. Publication Date: 2011 Feb |
Date Detail:
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Created Date: 2010-12-14 Completed Date: 2011-03-22 Revised Date: 2012-02-02 |
Medline Journal Info:
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Nlm Unique ID: 0370535 Medline TA: Anal Biochem Country: United States |
Other Details:
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Languages: eng Pagination: 112-22 Citation Subset: IM |
Copyright Information:
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Copyright © 2010 Elsevier Inc. All rights reserved. |
Affiliation:
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Mass Spectrometry Resource, Division of Endocrinology, Diabetes, Metabolism, and Lipid Research, Department of Internal Medicine, Washington University School of Medicine, St. Louis, MO 63110, USA. fhsu@im.wustl.edu |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Isomerism Mycolic Acids / chemistry* Rhodococcus equi / metabolism* Spectrometry, Mass, Electrospray Ionization / methods Tandem Mass Spectrometry |
| Grant Support | |
ID/Acronym/Agency:
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P01-HL-57278/HL/NHLBI NIH HHS; P30-DK56341/DK/NIDDK NIH HHS; P41 RR000954-23/RR/NCRR NIH HHS; P41 RR000954-25/RR/NCRR NIH HHS; P41 RR000954-27/RR/NCRR NIH HHS; P41 RR000954-28/RR/NCRR NIH HHS; P41 RR000954-30/RR/NCRR NIH HHS; P41 RR000954-32/RR/NCRR NIH HHS; P41 RR000954-33/RR/NCRR NIH HHS; P41 RR000954-33S1/RR/NCRR NIH HHS; P41 RR000954-34/RR/NCRR NIH HHS; P41-RR-00954/RR/NCRR NIH HHS; P60 DK020579-219005/DK/NIDDK NIH HHS; P60 DK020579-229005/DK/NIDDK NIH HHS; P60 DK020579-22S19005/DK/NIDDK NIH HHS; P60 DK020579-239005/DK/NIDDK NIH HHS; P60 DK020579-249005/DK/NIDDK NIH HHS; P60 DK020579-24S19005/DK/NIDDK NIH HHS; P60 DK020579-24S29005/DK/NIDDK NIH HHS; P60 DK020579-24S39005/DK/NIDDK NIH HHS; P60 DK020579-259005/DK/NIDDK NIH HHS; P60 DK020579-25S19005/DK/NIDDK NIH HHS; P60 DK020579-269005/DK/NIDDK NIH HHS; P60 DK020579-278787/DK/NIDDK NIH HHS; P60 DK020579-288808/DK/NIDDK NIH HHS; P60 DK020579-298817/DK/NIDDK NIH HHS; P60-DK-20579/DK/NIDDK NIH HHS; R37-DK-34388/DK/NIDDK NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Mycolic Acids; 0/meromycolic acids |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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