Document Detail

Hydrogen bonding in crystal forms of primary amide functionalised glucose and cellobiose.
MedLine Citation:
PMID:  23623957     Owner:  NLM     Status:  Publisher    
A glucoside and cellobioside of glycolamide were synthesised and the crystal chemistry of these compounds investigated. The amidoglucoside crystallised in the P21 space group. The primary amide group participates in C(7) and C(17) chains also involving the pyranose oxygen and hydroxyl groups. The amidocellobioside crystallised as a methanol solvate in the P21 space group. The amide N-H groups donate hydrogen bonds to oxygen atoms on the cellobiose units, while intramolecular hydrogen bonds give rise to S(7) and S(9) motifs in addition to a R3(3) (9) motif. A tetra-O-acetylglucoside derivative of thioglycolamide and its sulfoxide derivative were synthesised to examine the effect of protecting the glucopyranose hydroxyl groups. The thioglycolamido derivative, which crystallised in the P212121 space group, featured amide N-H groups donating to the glucopyranose oxygen and an acetyloxy group. The sulfoxy derivative crystallised in the P21 space group and featured the primary amide groups forming R2(3)(8) motifs generating a 21 ladder.
Humphrey A Moynihan; John A Hayes; Kevin S Eccles; Simon J Coles; Simon E Lawrence
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2013-4-2
Journal Detail:
Title:  Carbohydrate research     Volume:  374C     ISSN:  1873-426X     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  2013 Apr 
Date Detail:
Created Date:  2013-4-29     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  -    
Other Details:
Languages:  ENG     Pagination:  29-39     Citation Subset:  -    
Copyright Information:
Copyright © 2013 Elsevier Ltd. All rights reserved.
Department of Chemistry/Analytical and Biological Chemistry Research Facility, University College Cork, College Road, Cork, Ireland. Electronic address:
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