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Carbasugar-thioether pseudodisaccharides related to N-glycan biosynthesis.

Abstract:

Analogues of the alpha-Glcp-(1-->3)-alpha-Glcp and alpha-Glcp-(1-->3)-alpha-Manp disaccharides (representing the two alpha-gluco linkages cleaved by alpha-Glucosidase II in N-glycan biosynthesis) in which the non-reducing-end sugar is replaced by a carbasugar and the inter-glycosidic oxygen by a sulfur were synthesised. The key coupling step was an S(N)2 displacement of an equatorial triflate at C-1 of the carbasugar by C-3 gluco or manno thiolates with inversion of configuration to giv...

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Publication status:
Published

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Authors


Cumpstey, I More by this author
Alonzi, DS More by this author
Butters, TD More by this author
Journal:
Carbohydrate research
Volume:
344
Issue:
4
Pages:
454-459
Publication date:
2009-03-05
DOI:
EISSN:
1873-426X
ISSN:
0008-6215
URN:
uuid:de7bb8d9-b47f-4318-95c7-026c743f6cce
Source identifiers:
101111
Local pid:
pubs:101111

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