Block synthesis of tetra- and hexasaccharides (beta-D-glycero-D-manno-Hep p-(1-->4)-[alpha-l-Rha p-(1-->3)-beta-D-glycero-D-manno-Hep p-(1-->4)]n-alpha-L-Rha p-OMe (n = 1 and 2)) corresponding to multiple repeat units of the glycan from the surface-layer glycoprotein from Bacillus thermoaerophilus.

The Journal of Organic Chemistry
David Crich, Ming Li

Abstract

A fully stereocontrolled block synthesis of the title tetra- and hexasaccharides has been achieved taking advantage of the ability of the 4,6-O-benzylidene acetal to control the stereochemistry of the beta-D-glycero-D-mannoheptopyranoside unit and of a 2,3-O-diphenylmethylene acetal to install the alpha-L-rhamnopyranosidic linkages. Comparison of the spectral data for the hexasaccharide with that of the natural isolate confirms the structure of this very unusual and structurally challenging glycan.

References

Jan 1, 1995·Advances in Carbohydrate Chemistry and Biochemistry·I Tvaroska, F R Taravel
Jun 9, 2001·The Journal of Organic Chemistry·S E Denmark, J J Cottell
Nov 20, 2001·Chemical Reviews·S V LeyD J Reynolds
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Jul 30, 2004·Journal of the American Chemical Society·Henrik Helligsø JensenMikael Bols
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Apr 8, 2006·The Journal of Organic Chemistry·Hai DongOlof Ramström

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Citations

Nov 21, 2009·The Journal of Organic Chemistry·David Crich, Sébastien Picard
Jan 9, 2016·Chemistry : a European Journal·Martin A FascioneW Bruce Turnbull
Mar 8, 2017·The Journal of Organic Chemistry·Lukáš MaierKamil Paruch
Aug 13, 2011·Biomacromolecules·Sumati BhatiaAshok K Prasad

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