The crystal and molecular structure of hexa-O-acetyl-carrabiose dimethyl acetal

Lamba, Doriano; Burden, Cenydd; Mackie, William; Sheldrick, B.

doi:10.1016/s0008-6215(00)90129-0

Cited by 9 publications

(3 citation statements)

References 13 publications

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“…However, parameters for sulfated carbohydrates were developed using different force fields 4–9. New fiber diffraction studies of oriented carrageenan fibers were carried out,10, 11 as well as single crystal studies of low‐molecular weight analogs 12, 13. Several modeling studies of the disaccharide repeating units of carrageenans have been carried out using different force fields 3, 14–22.…”

Section: Introductionmentioning

confidence: 99%

MM3 potential energy surfaces of trisaccharides. II. Carrageenan models containing 3,6‐anhydro‐D‐galactose

Stortz

Cerezo

2003

Biopolymers

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The adiabatic potential energy surfaces (PES) of six trisaccharides-namely 3,6-An-alpha-D-Galp-(1-->3)-beta-D-Galp-(1-->4)-3,6-An-alpha-D-Galp, beta-D-Galp-(1-->4)-3,6-An-alpha-D-Galp-(1-->3)-beta-D-Galp, and their derivatives sulfated on positions 2 and 4 of the beta-galactose unit-were obtained using the MM3 force field. Each PES was described by a single contour map for which the energy is plotted against the two psi glycosidic angles, given the small variations of the phi glycosidic torsional angle in the low-energy regions of disaccharide maps. In five of the six examples, the surfaces are those expected from the maps of the disaccharidic repeating units of carrageenans, with less important factors altering the additive effect of both linkages. However, when a sulfate group is present on C2 of a beta-galactose reducing end, a new low-energy minimum in a different region is produced, originated in a hydrogen bond between the first and third monosaccharidic moieties of the trisaccharide. The flexibility of the beta-linkages is nearly identical to that in their disaccharide counterparts, while that of the alpha-linkages is slightly reduced, independent of their presence closer or further away from the reducing end. A fair agreement is observed between the x-ray fiber diffraction analysis for a kappa-carrageenan double helix and the surfaces obtained for the trisaccharide analogs of that polymer.

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Section: Introductionmentioning

confidence: 99%

MM3 potential energy surfaces of trisaccharides. II. Carrageenan models containing 3,6‐anhydro‐D‐galactose

Stortz

Cerezo

2003

Biopolymers

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“…In addition, the packing ratio is 21.3 Å 3 . While this value is slightly higher than typically observed for the packing of sugars without hydrogen bonds (17.5-19.2 Å 3 ), it is likely due to the fact that nearly 60% of the atoms in (I) are H atoms (Foces-Foces et al, 1980;Lamba et al, 1986).…”

Section: Figurementioning

confidence: 69%

A fused [3.3.0]-neoglycoside lactone derived from glucuronic acid

et al. 2013

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The bridged next-generation aminoglycoside (neoglycoside), 1-deoxy-1-[(methoxy)methylamino)]-2,5-di-O-triethylsilyl-β-D-glucofuranurono-γ-lactone {systematic name: (3S,3aS,5R,6R,6aS)-5-[methoxy(methyl)amino]-3,6-bis[(triethylsilyl)oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-2-one}, C20H41NO6Si2, was synthesized in a one-pot manner from commercially available D-glucuronic acid. This structure supports the properties associated with the anomeric effect for furanosides and can be employed to provide insight into the mechanisms by which alkoxyamine-appended natural products derive their enhanced biological activity. To the best of our knowledge, this is the first published crystal structure of a bicyclic neoglycoside and is the first neoglycoside to be completely and unambiguously characterized.

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“…In consequence, we have endeavoured to explore the use of low molecular weight model compounds for obtaining reliable stereochemical data (15,16). For example, X-ray crystallographic studies can provide information on hydrogen bonding and cation coordination that may be useful for modelling the polymer chains.…”

Section: Introductionmentioning

confidence: 99%

Novel Synthesis of monosulphated methyl α-D-galactopyranosides

Rashid¹,

Mackie²,

Colquhoun³

et al. 1990

Can. J. Chem.

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DORIANO LAMBA. Can. J. Chem. 68, 1122Chem. 68, (1990. The syntheses of the methyl u-D-galactopyranoside 2-, 3-, 4-, and 6-sulphates (11, 12, 16, and 21 respectively) have been achieved using trimethylamine -sulphur trioxide as the sulphating agent. The procedure used is high yielding and requires shorter reaction times than reported previously. Each compound was obtained in a crystalline form as the potassium salt. Improved syntheses are described of the 3,4-isopropylidene acetal2 of the methyl u-D-galactopyranoside and methyl.2-O-acetyl 4,6-O-benzylidene a-D-galactopyranoside 8, which are starting materials in the preparation of the 2-and 3-sulphates (11 and 12 respectively). An efficient route has been devised for the synthesis of methyl 2,3,6-tri-O-acetyl-a-D-galactopyranoside 14 using a base-catalysed transesterification (C4-OH+ C6-OH).

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The crystal and molecular structure of hexa-O-acetyl-carrabiose dimethyl acetal

Cited by 9 publications

References 13 publications

MM3 potential energy surfaces of trisaccharides. II. Carrageenan models containing 3,6‐anhydro‐D‐galactose

MM3 potential energy surfaces of trisaccharides. II. Carrageenan models containing 3,6‐anhydro‐D‐galactose

A fused [3.3.0]-neoglycoside lactone derived from glucuronic acid

Novel Synthesis of monosulphated methyl α-D-galactopyranosides

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