Biomaterial Database

Boat conformations synthesis, NMR spectroscopy, and molecular dynamics of methyl 4,6-O-benzylidene-3-deoxy-3-phthalimido-alpha-D-altropyranoside derivatives. 2001

B Coxon, and R C Reynolds

National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, MD 20892-2720, USA. coxonb@mail.nih.gov

Addition of the elements of phthalimide to methyl 2,3-anhydro-4,6-O-benzylidene-alpha-D-mannopyranoside (1) under fusion conditions has yielded methyl 4,6-O-benzylidene-3-deoxy-3-phthalimido-alpha-D-altropyranoside (2). The conformation of the pyranose ring of 2 has been shown to be non-chair by 1H NMR spectroscopy, in contrast to the conformations of related derivatives having smaller substituents at C-3. Molecular dynamics simulations of 2 in explicit chloroform-d solvent have indicated four principal conformational possibilities. Of these, the 7C5/1S5 chair/skew boat form 2d has the lowest potential energy, and is largely consistent with the observed vicinal 1H-1H NMR coupling constants.

UI	MeSH Term	Description	Entries
D009038	Motion	Physical motion, i.e., a change in position of a body or subject as a result of an external force. It is distinguished from MOVEMENT, a process resulting from biological activity.	Motions
D010797	Phthalimides	The imide of phthalic acids.
D002236	Carbohydrate Conformation	The characteristic 3-dimensional shape of a carbohydrate.	Carbohydrate Linkage,Carbohydrate Conformations,Carbohydrate Linkages,Conformation, Carbohydrate,Conformations, Carbohydrate,Linkage, Carbohydrate,Linkages, Carbohydrate
D003837	Deoxy Sugars	Sugars that in which one or more hydroxyl groups of the pyranose or furanose ring is substituted by hydrogen.	Deoxy Sugar,Sugar, Deoxy,Sugars, Deoxy
D019906	Nuclear Magnetic Resonance, Biomolecular	NMR spectroscopy on small- to medium-size biological macromolecules. This is often used for structural investigation of proteins and nucleic acids, and often involves more than one isotope.	Biomolecular Nuclear Magnetic Resonance,Heteronuclear Nuclear Magnetic Resonance,NMR Spectroscopy, Protein,NMR, Biomolecular,NMR, Heteronuclear,NMR, Multinuclear,Nuclear Magnetic Resonance, Heteronuclear,Protein NMR Spectroscopy,Biomolecular NMR,Heteronuclear NMR,Multinuclear NMR,NMR Spectroscopies, Protein,Protein NMR Spectroscopies,Spectroscopies, Protein NMR,Spectroscopy, Protein NMR