Location of functional groups in mycobacterial meromycolate chains; the recognition of new structural principles in mycolic acids

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Location of functional groups in mycobacterial meromycolate chains; the recognition of new structural principles in mycolic acids. / Watanabe, M; Aoyagi, Y; Mitome, H; Fujita, T; Naoki, H; Ridell, M; Minnikin, David.

In: Microbiology, Vol. 148, 01.06.2002, p. 1881-1902.

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Watanabe M, Aoyagi Y, Mitome H, Fujita T, Naoki H, Ridell M et al. Location of functional groups in mycobacterial meromycolate chains; the recognition of new structural principles in mycolic acids. Microbiology. 2002 Jun 1;148:1881-1902.

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Watanabe, M ; Aoyagi, Y ; Mitome, H ; Fujita, T ; Naoki, H ; Ridell, M ; Minnikin, David. / Location of functional groups in mycobacterial meromycolate chains; the recognition of new structural principles in mycolic acids. In: Microbiology. 2002 ; Vol. 148. pp. 1881-1902.

Bibtex

@article{96e568058c09472f8f14c3a5c495f674,
title = "Location of functional groups in mycobacterial meromycolate chains; the recognition of new structural principles in mycolic acids",
abstract = "Mycobacterial alpha-, methoxy- and keto-mycolic acid methyll esters were separated by argentation chromatography into mycolates with no double bond, with one trans double bond or with one cis double bond. Meromycolic acids were prepared from each methyl mycolate fraction by pyrolysis, followed by silver oxide oxidation, and analysed by high-energy collision-induced dissociation/fast atom bombardment MS to reveal the exact locations of the functional groups within the meromycolate chain. The locations of cis and trans double bonds, cis and trans cyclopropane rings, methoxy and keto groups, and methyl branches within the meromycolate chain were determined from their characteristic fragment ion profiles, and the structures of the meromycolic acids, including those with three functional groups extracted from Mycobacterium tuberculosis H37Ra, Mycobacterium bovis BCG and Mycobacterium microti, were established. Meromycolic acids with one cis double bond were structurally closely related to those with one cis cyclopropane ring, whereas the meromycolic acids with one trans cyclopropane ring were closely related to the corresponding meromycolic acids with one cis cyclopropane ring. A close relationship between methoxy- and keto-meromycolic acids was also implied. The relationship between the meromycolic acids with a trans double bond and the other meromycolic acids was not clearly revealed, and they did not appear to be immediate substrates for trans cyclopropanation.",
keywords = "meromycolic acids, CID mass spectrometry, spacing between functional groups",
author = "M Watanabe and Y Aoyagi and H Mitome and T Fujita and H Naoki and M Ridell and David Minnikin",
year = "2002",
month = jun,
day = "1",
language = "English",
volume = "148",
pages = "1881--1902",
journal = "Microbiology",
issn = "1350-0872",
publisher = "Society for General Microbiology",

}

RIS

TY - JOUR

T1 - Location of functional groups in mycobacterial meromycolate chains; the recognition of new structural principles in mycolic acids

AU - Watanabe, M

AU - Aoyagi, Y

AU - Mitome, H

AU - Fujita, T

AU - Naoki, H

AU - Ridell, M

AU - Minnikin, David

PY - 2002/6/1

Y1 - 2002/6/1

N2 - Mycobacterial alpha-, methoxy- and keto-mycolic acid methyll esters were separated by argentation chromatography into mycolates with no double bond, with one trans double bond or with one cis double bond. Meromycolic acids were prepared from each methyl mycolate fraction by pyrolysis, followed by silver oxide oxidation, and analysed by high-energy collision-induced dissociation/fast atom bombardment MS to reveal the exact locations of the functional groups within the meromycolate chain. The locations of cis and trans double bonds, cis and trans cyclopropane rings, methoxy and keto groups, and methyl branches within the meromycolate chain were determined from their characteristic fragment ion profiles, and the structures of the meromycolic acids, including those with three functional groups extracted from Mycobacterium tuberculosis H37Ra, Mycobacterium bovis BCG and Mycobacterium microti, were established. Meromycolic acids with one cis double bond were structurally closely related to those with one cis cyclopropane ring, whereas the meromycolic acids with one trans cyclopropane ring were closely related to the corresponding meromycolic acids with one cis cyclopropane ring. A close relationship between methoxy- and keto-meromycolic acids was also implied. The relationship between the meromycolic acids with a trans double bond and the other meromycolic acids was not clearly revealed, and they did not appear to be immediate substrates for trans cyclopropanation.

AB - Mycobacterial alpha-, methoxy- and keto-mycolic acid methyll esters were separated by argentation chromatography into mycolates with no double bond, with one trans double bond or with one cis double bond. Meromycolic acids were prepared from each methyl mycolate fraction by pyrolysis, followed by silver oxide oxidation, and analysed by high-energy collision-induced dissociation/fast atom bombardment MS to reveal the exact locations of the functional groups within the meromycolate chain. The locations of cis and trans double bonds, cis and trans cyclopropane rings, methoxy and keto groups, and methyl branches within the meromycolate chain were determined from their characteristic fragment ion profiles, and the structures of the meromycolic acids, including those with three functional groups extracted from Mycobacterium tuberculosis H37Ra, Mycobacterium bovis BCG and Mycobacterium microti, were established. Meromycolic acids with one cis double bond were structurally closely related to those with one cis cyclopropane ring, whereas the meromycolic acids with one trans cyclopropane ring were closely related to the corresponding meromycolic acids with one cis cyclopropane ring. A close relationship between methoxy- and keto-meromycolic acids was also implied. The relationship between the meromycolic acids with a trans double bond and the other meromycolic acids was not clearly revealed, and they did not appear to be immediate substrates for trans cyclopropanation.

KW - meromycolic acids

KW - CID mass spectrometry

KW - spacing between functional groups

M3 - Article

C2 - 12055308

VL - 148

SP - 1881

EP - 1902

JO - Microbiology

JF - Microbiology

SN - 1350-0872

ER -