Methyl α- and β-D-idopyranosiduronic acids synthesis and conformational analysis

Perlin, Arthur S.; Casu, Benito; Sanderson, G. R.; Tse, Janet M.

doi:10.1016/s0008-6215(00)81737-1

Cited by 68 publications

(15 citation statements)

References 31 publications

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“…However, a 1 C 4 conformation appears to be significantly populated for the a-and (to a lesser extent) b-anomers of D D-idose (populations $80% and $25% for the a-and b-anomers, respectively 30 ), as well as D D-altrose and (possibly) D D-gulose (population ratios unknown). This alternative chair conformation may become dominant for some D D-monosaccharide derivatives (e.g., of glucose, 194,325 idose, 59,83,326 xylose 327 and iduronates 48,51,54,57,58,60,328 ). Most (empirical or theoretical) estimates suggest a stability difference comprised between 25 and 45 kJ mol À1 between the two chair conformations of Glc in the gas-phase.…”

Section: Ring Conformationmentioning

confidence: 99%

Conformation, dynamics, solvation and relative stabilities of selected β-hexopyranoses in water: a molecular dynamics study with the gromos 45A4 force field

Kräutler

Müller

Hünenberger

2007

Carbohydrate Research

139

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Section: Ring Conformationmentioning

confidence: 99%

Conformation, dynamics, solvation and relative stabilities of selected β-hexopyranoses in water: a molecular dynamics study with the gromos 45A4 force field

Kräutler

Müller

Hünenberger

2007

Carbohydrate Research

139

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“…spectroscopy and hence also demonstrates the superior potential of this method for the measurement of 13C spectra of carbohydrate macromolecules. 'Postdoctoral Fellow, 1970-1971-1972, respectively.…”

mentioning

confidence: 99%

The ¹³C Fourier Transform Spectrum of Heparin. Evidence for a Biose Repeating Sequence of Residues

Perlin¹,

Kin²,

Bhattacharjee³

et al. 1972

Can. J. Chem.

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Carbon-13 Fourier transform n.m.r. spectra of the biopolymer, heparin, are described. The protondecoupled spectrum corresponds to that of a molecular structure based on 12 carbon atoms, and the observed chemical shifts are shown to be consistent with a previously-proposed alternating sequence consisting of (I -t 4) linked residues of a-L-idopyranosyluronic acid 2-sulfate and 2-deoxy-2-sulfamino-a-Dglucopyranosyl 6-sulfate. Line-broadening of the C-6 signal of the latter residue indicates that spin-spin relaxation of the 13C nucleus of this sulfated primary carbinol group is more effective than for the 13C nuclei of the sugar rings. Among model compounds utilized for assignment of the signals from heparin is a disaccharide, 4-0-(a-L-idopyranosyluronic acid 2-sulfate)-2,5-anhydro-D-mannose 6-sulfate, prepared in 65% yield by deaminative degradation of heparin.Les spectres carbone 13, transformes de Fourier, du biopolymtre htparine sont dCcrits. Le spectre, avec les protons dtcouplts, correspond a celui d'une structure moltculaire contenant douze atomes de carbone; on a montrt que les deplacements chimiques observts sont compatibles avec la stquence alternte que nous avons prtctdemment proposte, consistant des rtsidus a-L-iodopyranosyluronique acide sulfate-2 et dtoxy-2 sulfamino-2-a-D-glucopyranosyl sulfate-6, lits (1 +4). La largeur de raie du signal C-6 du dernier residu indique que la relaxation spin-spin du noyau 13C de ce groupe carbinol primaire sulfate est plus facile que celle des noyaux 13C pour les cycles des sucres. Parmi les composts modtles utilists pour l'attribution des signaux de I'htparine nous signalons que le disaccharide 4-0-(a-L-iodopyranosyl uronique acide sulfate-2) anhydro-2,5-D-mannose sulfate-6 a t t t prtpart avec un rendement de 65% par degradation dtaminative de l'htparine.

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“…The catalytic oxidation of 5 to 6 was effected by the method of Perlin et al (28), using a platinum-on-carbon catalyst in an aqueous reaction medium at 50°C. The pH of the reaction solution was monitored continuously and maintained at 7.5 by the addition of small increments of sodium hydrogen carbonate until a stoichiometric quantity had been utilized.…”

Section: Resultsmentioning

confidence: 99%

L-Glucose. A convenient synthesis from D-glucose

Szarek¹,

Hay²,

Vyas³

et al. 1984

Can. J. Chem.

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Methyl α- and β-D-idopyranosiduronic acids synthesis and conformational analysis

Cited by 68 publications

References 31 publications

Conformation, dynamics, solvation and relative stabilities of selected β-hexopyranoses in water: a molecular dynamics study with the gromos 45A4 force field

Conformation, dynamics, solvation and relative stabilities of selected β-hexopyranoses in water: a molecular dynamics study with the gromos 45A4 force field

The ¹³C Fourier Transform Spectrum of Heparin. Evidence for a Biose Repeating Sequence of Residues

L-Glucose. A convenient synthesis from D-glucose

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Methyl α- and β-D-idopyranosiduronic acids synthesis and conformational analysis

Cited by 68 publications

References 31 publications

Conformation, dynamics, solvation and relative stabilities of selected β-hexopyranoses in water: a molecular dynamics study with the gromos 45A4 force field

Conformation, dynamics, solvation and relative stabilities of selected β-hexopyranoses in water: a molecular dynamics study with the gromos 45A4 force field

The 13C Fourier Transform Spectrum of Heparin. Evidence for a Biose Repeating Sequence of Residues

L-Glucose. A convenient synthesis from D-glucose

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The ¹³C Fourier Transform Spectrum of Heparin. Evidence for a Biose Repeating Sequence of Residues