title: Synthesis of N-(β-D-glycuronopyranosyl)alkanamides and 1-(β-D-glycuronopyranosyl)-4-phenyl-[1,2,3]-triazoles as N-glycoprotein linkage region analogs: examination of the effect of C5 substituent on the N-glycosidic torsion (ΦN) based on X-ray crystallography.
abstract: The torsion angle around the N-glycoprotein linkage region (GlcNAc-Asn) is an important factor for presenting sugar on the cell surface which is crucial for many biological processes. Earlier studies using model and analogs showed that this important torsion angle is greatly influenced by substitutions in the sugar part. In the present work, uronic acid alkanamides and triazole derivatives have been designed and synthesized as newer analogs of N-glycoprotein linkage region to understand the influence of the carboxylic group on linkage region torsion as well as on molecular packing. Crystal structure of N-(β-D-galacturonopyranosyl)acetamide is solved with the space group of P22121. Comparison of the torsion angle and molecular packing of this compound with N-(β-D-galactopyranosyl)acetamide showed that changing the C6-hydoxymethyl group to the carboxylic acid group has minimum influence on the N-glycosidic torsion angle, ΦN and significant influence on the molecular packing.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India. Electronic address: mathi24@gmail.com.
authors.forename: Manoharan
authors.initials: M
authors.lastname: Mathiselvam
authors.forename: Duraikkannu
authors.initials: D
authors.lastname: Loganathan
authors.forename: Babu
authors.initials: B
authors.lastname: Varghese
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D040761:Biomimetic Materials / Q000138:chemical synthesis / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D006023:Glycoproteins / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D008958:Models, Molecular; D011487:Protein Conformation; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D014574:Uronic Acids / Q000737:chemistry
chemical_list: D000577:Amides; D006023:Glycoproteins; D006027:Glycosides; D014230:Triazoles; D014574:Uronic Acids
keywords: Linkage region; N-Glycoprotein; N-Glycosidic torsion; Uronic acid; X-ray crystallography