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Amphiphilk carbohydrates as a tool for molecular recognition in organized systems

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Glycoscience Synthesis of Substrate Analogs and Mimetics

Part of the book series: Topics in Current Chemistry ((4143,volume 187))

Abstract

Organized assemblies of carbohydrates are spontaneously formed when glycolipids or synthetically hydrophobized carbohydrates are dispersed in water (possibly in the presence of other lipids). Carbohydrate recognition of such organized systems (mono or bilayers) is somewhat different from recognition in isotropic media. The main differences arise from the kinetics and thermodynamics points of view (hindered approach and entropy changes at the surface, respectively). Furthermore, the conformation and the motion of the carbohydrate embedded at interfaces are strongly affected by the natures of its lipid anchor and that of the surrounding lipid components. The self-organization of amphiphilic carbohydrates can be rationalized by considering the geometry of the molecule; depending on the surface of the polar head, length and volume of the apolar tail, micelles, liquid crystals, monolayers, or vesicles can be formed. The recognition, by specific receptors, of carbohydrates assembled as monolayers or Langmuir-Blodgett films, can display quantitative information such as the thermodynamic parameters of binding or cluster effects, whereas the recognition at the surface of vesicles mainly affords a qualitative knowledge of the binding.

This paper is not a review covering the entire field of carbohydrate-recognition in any organized system. Many excellent papers have already been devoted to supramolecular systems such as cyclodextrins, podands, coronands or cryptants able to entrap carbohydrate molecules [1]. This article only deals with the molecular recognition of mono and oligosaccharides in organized self-assemblies of amphiphilic carbohydrates (possibly blended with other lipids) in aqueous medium; i.e. in assemblies mimicking the cell membrane.

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Abbreviations

Cer:

Ceramide

CHAPSO:

3-[(CHolAmidopropyl)dimethylammonio]-2-hydroxyl-1-PropaneSulfOnate

cmc:

Critical Micellar Concentration

Con A:

Concavalin A

DMPC:

L-α-DiMyristoylPhosphatidylCholine

EFO:

Evanescent Fiber Optic

FITC:

Fluorescein IsoThioCyanate

GbO3 :

Galα(1-4)Galα(1-4)Glcβ-Cer

GbO4 :

GalNAcβ(1 -3)Galα(1 -4)Galα(1-4)Glcβ-Cer

GbO5 :

GalNAcα(1-3)GalNAcβ(1 -3)Galα(1-4)Galα(1 -4)Glcβ-Cer

GPI:

GlycosylPhosphatidyl Inositol

H-:

Hydrophobized

HLB:

Hydrophilic Lipophilic Balance

IgG:

Immunoglobulin G

IgM:

Immunoglobulin M

Lac:

Lactose

LB:

Langmuir-Blodgett

LUV:

Large Unilamellar Vesicle

Mal:

Maltose

MLV:

MultiLamellar Vesicle

PC:

Phosphatidyl Choline

PE:

Phosphatidyl Ethanolamine

QCM:

Quartz Crystal Microbalance

RET:

Resonance Energy Transfer

SEM:

Scanning Electron Microscopy

SFA:

Surface Force Apparatus

Sug-A:

Aldonic acid (any carbohydrate in oxidized form)

Sug-ol:

Sugar alditol (any carbohydrate in reduced form)

SUV:

Small Unilamellar Vesicle

TBDMS:

tert-ButylDiMethylSilyl

TMSOTf:

TriMethylSilyl TriFluoromethanesulfonate

WGA:

Wheat Germ Agglutinin

2D, 3D:

Two-Dimensional, Three-Dimensional

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  1. Université Claude-Bernard-Lyon 1, C.P.E. Lyon, Laboratoire Chimie Organique 2, U.M.R. C. N. R. S. 5622, 69622, Villeurbanne cedex, France

    Paul Boullanger

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  1. Paul Boullanger
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Hugues Driguez Joachim Thiem

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© 1997 Springer Verlag Berlin Heidelberg

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Boullanger, P. (1997). Amphiphilk carbohydrates as a tool for molecular recognition in organized systems. In: Driguez, H., Thiem, J. (eds) Glycoscience Synthesis of Substrate Analogs and Mimetics. Topics in Current Chemistry, vol 187. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0119260

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  • DOI: https://doi.org/10.1007/BFb0119260

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