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Characteristic fragmentation of bacteriohopanepolyols during atmospheric pressure chemical ionisation liquid chromatography/ion trap mass spectrometry

Characteristic fragmentation of bacteriohopanepolyols during atmospheric pressure chemical... Bacteriohopanepolyols (BHPs) fragment via characteristic pathways during atmospheric pressure chemical ionisation liquid chromatography/ion trap mass spectrometry (APCI‐LC/MSn). Comparison of the MS2 spectra of bacteriohopane‐32,33,34,35‐tetrol (BHT) and 2β‐methylbacteriohopane‐32,33,34,35‐tetrol has confirmed the previously proposed ring‐C cleavage occurring between C‐9 and 11 and C‐8 and 14. This fragmentation, diagnostic of all hopanoids, also occurs in BHPs containing an amino group (‐NH2) at C‐35 although the higher relative stability of the ion limits this fragmentation to a minor process after protonation of the basic nitrogen function. Studies of a number of cell cultures including a prochlorophyte (Prochlorothrix hollandica) and a cyanobacterium (Chlorogloeopsis LA) demonstrate the power of this technique to detect composite BHPs with a complex biological functionality at C‐35. We also report the first observation of intact pentafunctionalised bacteriohopanepolyols using this method. Copyright © 2003 John Wiley & Sons, Ltd. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Rapid Communications in Mass Spectrometry Wiley

Characteristic fragmentation of bacteriohopanepolyols during atmospheric pressure chemical ionisation liquid chromatography/ion trap mass spectrometry

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References (11)

Publisher
Wiley
Copyright
Copyright © 2003 Wiley Subscription Services
ISSN
0951-4198
eISSN
1097-0231
DOI
10.1002/rcm.1265
pmid
14673828
Publisher site
See Article on Publisher Site

Abstract

Bacteriohopanepolyols (BHPs) fragment via characteristic pathways during atmospheric pressure chemical ionisation liquid chromatography/ion trap mass spectrometry (APCI‐LC/MSn). Comparison of the MS2 spectra of bacteriohopane‐32,33,34,35‐tetrol (BHT) and 2β‐methylbacteriohopane‐32,33,34,35‐tetrol has confirmed the previously proposed ring‐C cleavage occurring between C‐9 and 11 and C‐8 and 14. This fragmentation, diagnostic of all hopanoids, also occurs in BHPs containing an amino group (‐NH2) at C‐35 although the higher relative stability of the ion limits this fragmentation to a minor process after protonation of the basic nitrogen function. Studies of a number of cell cultures including a prochlorophyte (Prochlorothrix hollandica) and a cyanobacterium (Chlorogloeopsis LA) demonstrate the power of this technique to detect composite BHPs with a complex biological functionality at C‐35. We also report the first observation of intact pentafunctionalised bacteriohopanepolyols using this method. Copyright © 2003 John Wiley & Sons, Ltd.

Journal

Rapid Communications in Mass SpectrometryWiley

Published: Jan 30, 2003

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