B. Coxon
Nov 23, 1999
Citations
0
Influential Citations
7
Citations
Journal
Carbohydrate Research
Abstract
Abstract Methyl 2,6-anhydro-3-deoxy-3-phthalimido-α- d -mannopyranoside and its 15 N-labeled analog have been synthesized by reaction of methyl 2,6:3,4-dianhydro-α- d -altropyranoside with a mixture of phthalimide and potassium phthalimide or their 15 N-labeled analogs. The geometry of the skew conformation of the mannopyranoside derivative has been characterized by molecular dynamics with simulated annealing and correlated with vicinal and long-range 1 H 1 H and vicinal 1 H 15 N coupling constants measured by 1 H NMR spectroscopy. Dihedral angle comparisons have been made with derivatives of the parent 2,2,2-bicyclo-octane structure. The 1 H 15 N coupling constant data provide further values for definition of a Karplus equation for analysis of the stereochemistry of aminoglycosides.