Conformational behavior of oxygenated mycobacterial mycolic acids from Mycobacterium bovis BCG

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Conformational behavior of oxygenated mycobacterial mycolic acids from Mycobacterium bovis BCG. / Villeneuve, M; Kawai, M; Watanabe, M; Aoyagi, Y; Hitotsuyanagi, Y; Takeya, K; Gouda, H; Hirono, S; Minnikin, David; Nakahara, H.

In: Biochimica et Biophysica Acta (BBA) - Biomembranes, Vol. 1768, No. 7, 01.07.2007, p. 1717-1726.

Research output: Contribution to journalArticle

Harvard

Villeneuve, M, Kawai, M, Watanabe, M, Aoyagi, Y, Hitotsuyanagi, Y, Takeya, K, Gouda, H, Hirono, S, Minnikin, D & Nakahara, H 2007, 'Conformational behavior of oxygenated mycobacterial mycolic acids from Mycobacterium bovis BCG', Biochimica et Biophysica Acta (BBA) - Biomembranes, vol. 1768, no. 7, pp. 1717-1726. https://doi.org/10.1016/j.bbamem.2007.04.003

APA

Villeneuve, M., Kawai, M., Watanabe, M., Aoyagi, Y., Hitotsuyanagi, Y., Takeya, K., Gouda, H., Hirono, S., Minnikin, D., & Nakahara, H. (2007). Conformational behavior of oxygenated mycobacterial mycolic acids from Mycobacterium bovis BCG. Biochimica et Biophysica Acta (BBA) - Biomembranes, 1768(7), 1717-1726. https://doi.org/10.1016/j.bbamem.2007.04.003

Vancouver

Author

Villeneuve, M ; Kawai, M ; Watanabe, M ; Aoyagi, Y ; Hitotsuyanagi, Y ; Takeya, K ; Gouda, H ; Hirono, S ; Minnikin, David ; Nakahara, H. / Conformational behavior of oxygenated mycobacterial mycolic acids from Mycobacterium bovis BCG. In: Biochimica et Biophysica Acta (BBA) - Biomembranes. 2007 ; Vol. 1768, No. 7. pp. 1717-1726.

Bibtex

@article{c05ccfbcc2a14d3dafbe7c40d5d7f6ad,
title = "Conformational behavior of oxygenated mycobacterial mycolic acids from Mycobacterium bovis BCG",
abstract = "Phase diagrams of Langmuir monolayers of oxygenated mycolic acids, i.e. methoxy mycolic acid (MeO-MA), ketomycolic acid (Keto-MA), and artificially obtained deoxo-mycolic acid (deoxo-MA) from Mycobacterium bovis BCG were obtained by thermodynamic analysis of the surface pressure (pi) vs. average molecular area (A) isotherms. At lower temperatures and lower surface pressures, both Keto- and MeO-MAs formed rigid condensed monolayers where each MA molecule was considered to be in a 4-chain form, in which the three carbon chain segments due to bending of the 3-hydroxy aliphatic carboxylate chain and the 2-side chain were in compact parallel arrangement. At higher temperatures and surface pressures, MeO-MA and deoxo-MA tended to take stretched-out conformations in which the 3-hydroxy aliphatic carboxylate chain was more or less in an extended form, but Keto-MA retained the original 4-chain structure. The thickness measurement of the monolayers in situ by ellipsometry at different pi values and temperatures supported the above conclusions derived from the phase diagrams. The enthalpy changes associated with the phase transitions of MeO-MA and deoxo-MA implied that the MeO-MA needed larger energy to change from a compact conformation to an extended one, possibly and partly due to the dehydration of the methoxy group from water surface involved. Molecular dynamics studies of MA models derived from Monte Carlo calculations were also performed, which confirmed the conformational behavior of MAs suggested by the thermodynamic studies on the Langmuir monolayers.",
author = "M Villeneuve and M Kawai and M Watanabe and Y Aoyagi and Y Hitotsuyanagi and K Takeya and H Gouda and S Hirono and David Minnikin and H Nakahara",
year = "2007",
month = jul,
day = "1",
doi = "10.1016/j.bbamem.2007.04.003",
language = "English",
volume = "1768",
pages = "1717--1726",
journal = "Biochimica et Biophysica Acta (BBA) - Biomembranes",
issn = "0005-2736",
publisher = "Elsevier",
number = "7",

}

RIS

TY - JOUR

T1 - Conformational behavior of oxygenated mycobacterial mycolic acids from Mycobacterium bovis BCG

AU - Villeneuve, M

AU - Kawai, M

AU - Watanabe, M

AU - Aoyagi, Y

AU - Hitotsuyanagi, Y

AU - Takeya, K

AU - Gouda, H

AU - Hirono, S

AU - Minnikin, David

AU - Nakahara, H

PY - 2007/7/1

Y1 - 2007/7/1

N2 - Phase diagrams of Langmuir monolayers of oxygenated mycolic acids, i.e. methoxy mycolic acid (MeO-MA), ketomycolic acid (Keto-MA), and artificially obtained deoxo-mycolic acid (deoxo-MA) from Mycobacterium bovis BCG were obtained by thermodynamic analysis of the surface pressure (pi) vs. average molecular area (A) isotherms. At lower temperatures and lower surface pressures, both Keto- and MeO-MAs formed rigid condensed monolayers where each MA molecule was considered to be in a 4-chain form, in which the three carbon chain segments due to bending of the 3-hydroxy aliphatic carboxylate chain and the 2-side chain were in compact parallel arrangement. At higher temperatures and surface pressures, MeO-MA and deoxo-MA tended to take stretched-out conformations in which the 3-hydroxy aliphatic carboxylate chain was more or less in an extended form, but Keto-MA retained the original 4-chain structure. The thickness measurement of the monolayers in situ by ellipsometry at different pi values and temperatures supported the above conclusions derived from the phase diagrams. The enthalpy changes associated with the phase transitions of MeO-MA and deoxo-MA implied that the MeO-MA needed larger energy to change from a compact conformation to an extended one, possibly and partly due to the dehydration of the methoxy group from water surface involved. Molecular dynamics studies of MA models derived from Monte Carlo calculations were also performed, which confirmed the conformational behavior of MAs suggested by the thermodynamic studies on the Langmuir monolayers.

AB - Phase diagrams of Langmuir monolayers of oxygenated mycolic acids, i.e. methoxy mycolic acid (MeO-MA), ketomycolic acid (Keto-MA), and artificially obtained deoxo-mycolic acid (deoxo-MA) from Mycobacterium bovis BCG were obtained by thermodynamic analysis of the surface pressure (pi) vs. average molecular area (A) isotherms. At lower temperatures and lower surface pressures, both Keto- and MeO-MAs formed rigid condensed monolayers where each MA molecule was considered to be in a 4-chain form, in which the three carbon chain segments due to bending of the 3-hydroxy aliphatic carboxylate chain and the 2-side chain were in compact parallel arrangement. At higher temperatures and surface pressures, MeO-MA and deoxo-MA tended to take stretched-out conformations in which the 3-hydroxy aliphatic carboxylate chain was more or less in an extended form, but Keto-MA retained the original 4-chain structure. The thickness measurement of the monolayers in situ by ellipsometry at different pi values and temperatures supported the above conclusions derived from the phase diagrams. The enthalpy changes associated with the phase transitions of MeO-MA and deoxo-MA implied that the MeO-MA needed larger energy to change from a compact conformation to an extended one, possibly and partly due to the dehydration of the methoxy group from water surface involved. Molecular dynamics studies of MA models derived from Monte Carlo calculations were also performed, which confirmed the conformational behavior of MAs suggested by the thermodynamic studies on the Langmuir monolayers.

U2 - 10.1016/j.bbamem.2007.04.003

DO - 10.1016/j.bbamem.2007.04.003

M3 - Article

C2 - 17524352

VL - 1768

SP - 1717

EP - 1726

JO - Biochimica et Biophysica Acta (BBA) - Biomembranes

JF - Biochimica et Biophysica Acta (BBA) - Biomembranes

SN - 0005-2736

IS - 7

ER -