Crystal structure of an Amadori compound, N-(1-deoxy-β-d-fructopyranos-1-yl)-glycine (“d-fructose-glycine”)

✍ Scribed by Valeri V. Mossine; Gennadi V. Glinsky; Charles L. Barnes; Milton S. Feather

• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 521 KB
• Volume: 266
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(94)00256-f

✦ Synopsis

The first crystal structure data on an Amadori compound, N-(1-deoxy-/3-D-fructopyranos-l-yl)glycine, are reported. The space group is P21 with Z=2 and cell parameters a=7.246(1), b --10.009 (1), c = 7.060 (1)/~, and/3 = 101.085 (6) °. The structure was solved by direct methods and refined to a final R of 2.9% and Rw of 3.8% for 1385 reflections to give esd's of 0.002/~ in bond lengths and 0.2 ° in angles. The conformation of the carbohydrate is the normal 2C 5 pyranose chair. Bond lengths and valence angles compare well with average values from a number of pyranose structures. The molecule of the Amadori compound exists in the zwitterion form and has the C-6--O-6-C-2-C-1-N-C-2'-C-1'--0-1' chain in a zig-zag conformation, that is (together with 0-2') substantionally planar. All hydroxyl, carboxyl, and ring oxygen atoms, and the secondary ammonuim group are involved in hydrogen bonding, which forms a three-dimensional network of two infinite chains that have an ammonium group as a common segment. The shortest intra-and inter-molecular hydrogen bonds involve donors of the pyranosyl moiety and acceptors of the amino acid portion, and vice versa.