Monika Norkowska, H. Myszka, Magdalena Cyman
Jan 2, 2014
Citations
0
Influential Citations
4
Citations
Journal
Journal of Carbohydrate Chemistry
Abstract
2,3,4,6-tetra-O-Acetyl-D-gluconic acid was synthesized and coupled with 1,3,4, 6-tetra-O-acetyl-2-amino-2-deoxy-β-D-glucopyranose and diosgenyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside to afford N-gluconyl derivatives of diosgenyl 2-amino-2-deoxy-D-glucopyranoside using the methods of solution-phase peptide synthesis. Both coupling reactions suffered from acetyl O→N migration, which caused the N-acetyl derivatives to be formed together with the N-(D-gluconyl) derivatives of D-glucosamine. Additionally, single-crystal X-ray diffraction and high-resolution NMR spectral data for 2,3,4,6-tetra-O-acetyl-D-gluconic acid were analyzed to reveal that this acyclic carbohydrate has adopted the 2G− conformation instead of a typical zigzag conformation. The planarity and cis geometry of the acetoxyl groups are demonstrated.