Exploring the Effect of Bioisosteric Replacement of Carboxamide by a Sulfonamide Moiety on N-Glycosidic Torsions and Molecular Assembly: Synthesis and X-ray Crystallographic Investigation of N-(β-D-Glycosyl)sulfonamides as N-Glycoprotein Linkage Region An

Srivastava, Amrita ; Varghese, Babu ; Loganathan, Duraikkannu (2013) Exploring the Effect of Bioisosteric Replacement of Carboxamide by a Sulfonamide Moiety on N-Glycosidic Torsions and Molecular Assembly: Synthesis and X-ray Crystallographic Investigation of N-(β-D-Glycosyl)sulfonamides as N-Glycoprotein Linkage Region An Chemistry - A European Journal, 19 (52). pp. 17720-17732. ISSN 0947-6539

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Official URL: http://doi.org/10.1002/chem.201302018

Related URL: http://dx.doi.org/10.1002/chem.201302018

Abstract

Unique molecular assembly motif of GlcNAc: The different aglycon conformations of methanesulfonamido and chloromethanesulfonamido derivatives of GlcNAc as compared to other sulfonamido analogues is a unique feature of their molecular assembly. This could be due to the cumulative effect of the direct hydrogen bonding between N1 and O1′ and CH⋅⋅⋅O interactions of the aglycon chain.

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