Novel sugar bola-amphiphiles with a pseudo macrocyclic structure

Novel bola-amphiphilic compounds have been synthesised with d-glucose or d-galactose moieties as polar head groups. The sugar groups are coupled to the hydrophobic bridge, a chain of ten or twelve methylene groups, by an amide function at the C-2 site (2-alkylamido-2-deoxy- d-glucose derivative) or...

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Bibliographic Details
Published in:Carbohydrate research 1997-05, Vol.300 (4), p.341-346
Main Authors: Bertho, Jean-Noel, Coué, Annie, Ewing, David F., Goodby, John W., Letellier, Phillipe, Mackenzie, Grahame, Plusquellec, Daniel
Format: Article
Language:English
Subjects:
2-Alkylamido-2-deoxy- d-glucose
Bola-amphiphiles
d-Glycofuranuronamide
Glucose head groups
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Summary:Novel bola-amphiphilic compounds have been synthesised with d-glucose or d-galactose moieties as polar head groups. The sugar groups are coupled to the hydrophobic bridge, a chain of ten or twelve methylene groups, by an amide function at the C-2 site (2-alkylamido-2-deoxy- d-glucose derivative) or a glycuronamido function at the C-6 site. The former series is glycosylated with a cinnamyl group and the latter with octyl or decyl groups to afford pseudo macrocyclic compounds. Short synthetic routes to several new pseudo macrocylic bola-amphiphiles of the types shown are described. The short chain (SC) is cinnamyl, octyl or decyl
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(97)00071-2