Crystal Structure and Solid State NMR Analysis of N-(Methyl 3,4,6-Tri-O-Acetyl-2-Amino-2-Deoxy-β-D-Glucopyranoside)-N'Carbamoyl-D-Valine Ethyl Ester

• Published in: Journal of carbohydrate chemistry 1997-08, Vol.16 (6), p.739-749
• Main Authors: Anulewicz, Roma, Wawer, Iwona, Piekarska-Bartoszewicz, Boguslawa, Temeriusz, Andrzej
• Format: Article
• Language: English
• ISSN: 0732-8303; 1532-2327
• DOI: 10.1080/07328309708006538

The X-ray diffraction analysis of N-(methyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside)-N′-carbamoyl-D-valine ethyl ester has been performed establishing that molecules are associated by two types of NH...O hydrogen bonds. The N-1-H forms an intermolecular hydrogen bond with carbonyl oxygen, and the N-3-H forms a hydrogen bond with the anomeric oxygen, with distances 2.927(6) Å, and 3.063(7) Å, respectively. The urea moiety of the molecule is in the anti-Z,Z conformation. The signals in the 13 C CP MAS NMR spectrum are neither multiplied nor split, confirming that there is one molecule in the crystal asymmetric unit. The difference in chemical shifts between solid and solution spectra are significant for C-2, C-3 and OMe group of D-glucose moiety (1.7, 2.6 and 2.9 ppm respectively) and for NCON, Cα and Cβ D-valine carbon atoms.