Supramolecular stacking motifs in the solid state of amide and triazole derivatives of cellobiose

John A Hayes; Kevin S Eccles; Simon J Coles; Simon E Lawrence; Humphrey A Moynihan

doi:10.1016/j.carres.2014.02.011

Supramolecular stacking motifs in the solid state of amide and triazole derivatives of cellobiose

Carbohydr Res. 2014 Mar 31:388:67-72. doi: 10.1016/j.carres.2014.02.011. Epub 2014 Feb 18.

Authors

John A Hayes¹, Kevin S Eccles¹, Simon J Coles², Simon E Lawrence¹, Humphrey A Moynihan³

Affiliations

¹ Department of Chemistry / Analytical and Biological Chemistry Research Facility / Synthesis and Solid State Pharmaceutical Centre, University College Cork, College Road, Cork, Ireland.
² UK National Crystallographic Service, Chemistry, Faculty of Natural and Environmental Sciences, University of Southampton, Highfield, Southampton SO17 1BJ, UK.
³ Department of Chemistry / Analytical and Biological Chemistry Research Facility / Synthesis and Solid State Pharmaceutical Centre, University College Cork, College Road, Cork, Ireland. Electronic address: h.moynihan@ucc.ie.

PMID: 24631669
DOI: 10.1016/j.carres.2014.02.011

Abstract

1-Acetamido-1-deoxy-(4-O-β-d-glucopyranosyl-β-d-glucopyranose) (5) and 1-deoxy-1-(4-phenyl-1,2,3-triazolyl)-(4-O-β-d-glucopyranosyl-β-d-glucopyranose) (7) were synthesised from 1-azido-1-deoxy-(4-O-β-d-glucopyranosyl-β-d-glucopyranose) (2) and crystallised as dihydrates. Crystal structural analysis of 5·2H2O displayed an acetamide C(4) chain and stacked cellobiose residues. The structure of 7·2H2O featured π-π stacking and stacking of the cellobiose residues.

Keywords: Cellobiose; Crystal structure; Sugar amide; Sugar triazole.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemistry*
Cellobiose / analogs & derivatives*
Crystallization
Models, Molecular
Triazoles / chemistry*
Water / chemistry

Substances

Amides
Triazoles
Water
Cellobiose