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Boat conformations: synthesis, NMR spectroscopy, and molecular modeling of methyl 2,6-anhydro-3-deoxy-3-phthalimido-α-d-mannopyranoside and its15N-labeled analog

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
322
Identifiers
DOI: 10.1016/s0008-6215(99)00209-8
Keywords
  • 2
  • 6-Anhydrides
  • Boat Conformations
  • Carbon-13–Proton Chemical Shift Correlation
  • Carbon-13–Nitrogen-15 And Nitrogen-15–Proton Coupling Constants
  • Gradient-Enhanced 2D Hsqc
  • Mannopyranoside
  • Molecular Dynamics
  • Phthalimido Derivatives
  • Simulated Annealing
Disciplines
  • Chemistry
  • Mathematics

Abstract

Abstract Methyl 2,6-anhydro-3-deoxy-3-phthalimido-α- d-mannopyranoside and its 15N-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 15N-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 1H 1H and vicinal 1H 15N coupling constants measured by 1H NMR spectroscopy. Dihedral angle comparisons have been made with derivatives of the parent 2,2,2-bicyclo-octane structure. The 1H 15N coupling constant data provide further values for definition of a Karplus equation for analysis of the stereochemistry of aminoglycosides.

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