Conserved molecular superlattices in a series of homologous synthetic mycobacterial cell-wall lipids forming interdigitated bilayers

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Conserved molecular superlattices in a series of homologous synthetic mycobacterial cell-wall lipids forming interdigitated bilayers. / Martin-Bertelsen, Birte; Yaghmur, Anan; Franzyk, Henrik; Justesen, Sarah; Kirkensgaard, Jacob Judas Kain; Foged, Camilla.

In: Langmuir, Vol. 32, No. 48, 07.11.2016, p. 12693–12701.

Research output: Contribution to journalJournal articleResearchpeer-review

Harvard

Martin-Bertelsen, B, Yaghmur, A, Franzyk, H, Justesen, S, Kirkensgaard, JJK & Foged, C 2016, 'Conserved molecular superlattices in a series of homologous synthetic mycobacterial cell-wall lipids forming interdigitated bilayers', Langmuir, vol. 32, no. 48, pp. 12693–12701. https://doi.org/10.1021/acs.langmuir.6b01720

APA

Martin-Bertelsen, B., Yaghmur, A., Franzyk, H., Justesen, S., Kirkensgaard, J. J. K., & Foged, C. (2016). Conserved molecular superlattices in a series of homologous synthetic mycobacterial cell-wall lipids forming interdigitated bilayers. Langmuir, 32(48), 12693–12701. https://doi.org/10.1021/acs.langmuir.6b01720

Vancouver

Martin-Bertelsen B, Yaghmur A, Franzyk H, Justesen S, Kirkensgaard JJK, Foged C. Conserved molecular superlattices in a series of homologous synthetic mycobacterial cell-wall lipids forming interdigitated bilayers. Langmuir. 2016 Nov 7;32(48):12693–12701. https://doi.org/10.1021/acs.langmuir.6b01720

Author

Martin-Bertelsen, Birte ; Yaghmur, Anan ; Franzyk, Henrik ; Justesen, Sarah ; Kirkensgaard, Jacob Judas Kain ; Foged, Camilla. / Conserved molecular superlattices in a series of homologous synthetic mycobacterial cell-wall lipids forming interdigitated bilayers. In: Langmuir. 2016 ; Vol. 32, No. 48. pp. 12693–12701.

Bibtex

@article{de1c997974b442efb0e0ce1137e35052,
title = "Conserved molecular superlattices in a series of homologous synthetic mycobacterial cell-wall lipids forming interdigitated bilayers",
abstract = "Synthetic analogues of the cell-wall lipid monomycoloyl glycerol (MMG) are promising as next-generation vaccine adjuvants. In the present study, the thermotropic phase behaviour of an array of synthetic MMG analogues was examined using simultaneous small- and wide-angle X-ray scattering under excess water conditions. The MMG analogues differed in the alkyl chain lengths and in the stereochemistry of the polar glycerol headgroup or of the lipid tails (native-like versus alternative compounds). All MMG analogues formed poorly hydrated lamellar phases at low temperatures and inverse hexagonal (H2) phases at higher temperatures before melting. MMG analogues with a native-like lipid acid configuration self-assembled into non-interdigitated bilayers whereas the analogues displaying an alternative lipid acid configuration formed interdigitated bilayers in a subgel (Lc′) state. This is in contrast to previously described interdigitated phases for other lipids, which are usually in a gel (Lβ) state. All investigated MMG analogues displayed an abrupt direct temperature-induced phase transition from Lc′ to H2. This transition is ultimately driven by the lipid chain melting and the accompanying molecular shape change. No intermediate structures were found, but the entire array of MMG analogues displayed phase coexistence during the lamellae-H2 transition. The structural data also showed that the headgroups of the MMG analogues adopting the alternative lipid acid configuration were ordered and formed a two-dimensional molecular superlattice, which was conserved regardless of the lipid tail length. To our knowledge, the MMG analogues with an alternative lipid acid configuration represent the first example of a lipid system showing both interdigitation and superlattice formation and as such could serve as an interesting model system for future studies. The MMG analogues are also relevant from a subunit vaccine perspective because they are well-tolerated and display promising immunopotentiating activity. The structural characterization described here will serve as a prerequisite for the rational design of nanoparticulate adjuvants with specific and tailored structural features.",
author = "Birte Martin-Bertelsen and Anan Yaghmur and Henrik Franzyk and Sarah Justesen and Kirkensgaard, {Jacob Judas Kain} and Camilla Foged",
year = "2016",
month = "11",
day = "7",
doi = "10.1021/acs.langmuir.6b01720",
language = "English",
volume = "32",
pages = "12693–12701",
journal = "Langmuir",
issn = "0743-7463",
publisher = "American Chemical Society",
number = "48",

}

RIS

TY - JOUR

T1 - Conserved molecular superlattices in a series of homologous synthetic mycobacterial cell-wall lipids forming interdigitated bilayers

AU - Martin-Bertelsen, Birte

AU - Yaghmur, Anan

AU - Franzyk, Henrik

AU - Justesen, Sarah

AU - Kirkensgaard, Jacob Judas Kain

AU - Foged, Camilla

PY - 2016/11/7

Y1 - 2016/11/7

N2 - Synthetic analogues of the cell-wall lipid monomycoloyl glycerol (MMG) are promising as next-generation vaccine adjuvants. In the present study, the thermotropic phase behaviour of an array of synthetic MMG analogues was examined using simultaneous small- and wide-angle X-ray scattering under excess water conditions. The MMG analogues differed in the alkyl chain lengths and in the stereochemistry of the polar glycerol headgroup or of the lipid tails (native-like versus alternative compounds). All MMG analogues formed poorly hydrated lamellar phases at low temperatures and inverse hexagonal (H2) phases at higher temperatures before melting. MMG analogues with a native-like lipid acid configuration self-assembled into non-interdigitated bilayers whereas the analogues displaying an alternative lipid acid configuration formed interdigitated bilayers in a subgel (Lc′) state. This is in contrast to previously described interdigitated phases for other lipids, which are usually in a gel (Lβ) state. All investigated MMG analogues displayed an abrupt direct temperature-induced phase transition from Lc′ to H2. This transition is ultimately driven by the lipid chain melting and the accompanying molecular shape change. No intermediate structures were found, but the entire array of MMG analogues displayed phase coexistence during the lamellae-H2 transition. The structural data also showed that the headgroups of the MMG analogues adopting the alternative lipid acid configuration were ordered and formed a two-dimensional molecular superlattice, which was conserved regardless of the lipid tail length. To our knowledge, the MMG analogues with an alternative lipid acid configuration represent the first example of a lipid system showing both interdigitation and superlattice formation and as such could serve as an interesting model system for future studies. The MMG analogues are also relevant from a subunit vaccine perspective because they are well-tolerated and display promising immunopotentiating activity. The structural characterization described here will serve as a prerequisite for the rational design of nanoparticulate adjuvants with specific and tailored structural features.

AB - Synthetic analogues of the cell-wall lipid monomycoloyl glycerol (MMG) are promising as next-generation vaccine adjuvants. In the present study, the thermotropic phase behaviour of an array of synthetic MMG analogues was examined using simultaneous small- and wide-angle X-ray scattering under excess water conditions. The MMG analogues differed in the alkyl chain lengths and in the stereochemistry of the polar glycerol headgroup or of the lipid tails (native-like versus alternative compounds). All MMG analogues formed poorly hydrated lamellar phases at low temperatures and inverse hexagonal (H2) phases at higher temperatures before melting. MMG analogues with a native-like lipid acid configuration self-assembled into non-interdigitated bilayers whereas the analogues displaying an alternative lipid acid configuration formed interdigitated bilayers in a subgel (Lc′) state. This is in contrast to previously described interdigitated phases for other lipids, which are usually in a gel (Lβ) state. All investigated MMG analogues displayed an abrupt direct temperature-induced phase transition from Lc′ to H2. This transition is ultimately driven by the lipid chain melting and the accompanying molecular shape change. No intermediate structures were found, but the entire array of MMG analogues displayed phase coexistence during the lamellae-H2 transition. The structural data also showed that the headgroups of the MMG analogues adopting the alternative lipid acid configuration were ordered and formed a two-dimensional molecular superlattice, which was conserved regardless of the lipid tail length. To our knowledge, the MMG analogues with an alternative lipid acid configuration represent the first example of a lipid system showing both interdigitation and superlattice formation and as such could serve as an interesting model system for future studies. The MMG analogues are also relevant from a subunit vaccine perspective because they are well-tolerated and display promising immunopotentiating activity. The structural characterization described here will serve as a prerequisite for the rational design of nanoparticulate adjuvants with specific and tailored structural features.

U2 - 10.1021/acs.langmuir.6b01720

DO - 10.1021/acs.langmuir.6b01720

M3 - Journal article

C2 - 27934510

VL - 32

SP - 12693

EP - 12701

JO - Langmuir

JF - Langmuir

SN - 0743-7463

IS - 48

ER -

ID: 168629426