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Shaping Up for Structural Glycomics: A Predictive Protocol for Oligosaccharide Conformational Analysis Applied to N-Linked Glycans

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Shaping up for structural glycomics: a predictive protocol for oligosaccharide conformational analysis applied to N-linked glycans pr ly logy Received 28 August 2013 Received in revised form 17 October 2013 Accepted 19 October 2013 Available online 30 October 2013 Keywords: key to glycan recognition and a new era of rationally designed mimetic chemical probes, drugs, and bio- (NMR) spectroscopy and X-ray crystallography of N-linked sialyl Lewis antennae (1–2) and mannosyl cores (7–8).6–9 However, such studies have not yet elucidated the crucial link between sequence and protein specificity for this subset of the human glycome, ren- s. At a 3D-molec- d selectin active- rcibly restricting arides by ro selectin o pyranos stack together, forming a compact secondary-structure in and when protein bound,14 and they have been assumed to b chair-like puckers. Recent computational work has questioned the presumption that glycomic pyranoses are inflexible.15,16 Further- more, transiently occupied non-chair pyranose shapes may be the basis for selectivity in protein–oligosaccharide interactions and can be specifically targeted by ring-locked chemical analogs to increase biological activity.17 This suggests that a similar ap- proach could be applied to discover N-glycan conformational mimetics. Specifically, new 3D-insights into the molecular basis q This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. ⇑ Corresponding author. Tel.: +44 (0)161 306 4199; fax: +44 (0)161 306 5201. Carbohydrate Research 383 (2014) 34–42 Contents lists availab Carbohydrat .e l E-mail address: [email protected] (A. Almond). encoded by oligosaccharides are largely undeciphered and repre- sent a vast source of information for use in the design of new bio- materials, chemical probes, and drugs.3,4 A c

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