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- Title
Extending the Glucosyl Ceramide Cassette Approach: Application in the Total Synthesis of Ganglioside GalNAc-GM1b.
- Authors
Miku Konishi; Akihiro Imamura; Kohki Fujikawa; Hiromune Ando; Hideharu Ishida; Makoto Kiso
- Abstract
The development of a novel cyclic glucosyl ceramide cassette acceptor for efficient glycolipid syntheses was investigated. p-Methoxybenzyl (PMB) groups were selected as protecting groups at C2 and C3 of the glucose residue with the aim of improving the functionality of the cassette acceptor. The choice of the PMB group resulted in a loss of β-selectivity, which was corrected by using an appropriate tether to control the spatial arrangement and the nitrile solvent effect. To investigate the effect of linker structure on the β-selectivity of intramolecular glycosylation, several linkers for tethering the glucose and ceramide moiety were designed and prepared, namely, succinyl, glutaryl, dimethylmalonyl, and phthaloyl esters. The succinyl ester linker was the best for accessing the cassette form. The newly designed glucosyl ceramide cassette acceptor was then applied in the total synthesis of ganglioside GalNAc-GM1b.
- Subjects
MONOSACCHARIDES; ORGANIC compounds; SUCROSE; GLYCOSYLATION; SUGAR
- Publication
Molecules, 2013, Vol 18, Issue 12, p15153
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules181215153