A new synthesis of 3-acetamido-3-deoxy-<scp>d</scp>-glucose

Williams, D. T.; Jones, J. K. N.

doi:10.1139/v67-002

Cited by 30 publications

(13 citation statements)

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“…The hydroxymethyl group populations give good confirmatory support for the chain conformations (Tables 3 and 4). The 0,, 0,, and 0, hydroxymethyl group values for galactitol (53, 16,31) and D-mannitol (54, 46, 0) were taken" as characteristic for a planar chain lyxo-and arabino-configuration, respectively. The hydroxymethyl group values (58,1S, 27) for 1-deoxy-L-galactitol (5) show that the C-34-6 part of the chain is not as conformationally pure as in galactitol.…”

Section: %mentioning

confidence: 99%

1H nuclear magnetic resonance spectra and conformations of deoxyalditols in deuterium oxide

Gillies¹,

Lewis²

1985

J. Chem. Soc., Perkin Trans. 2

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The 'H n.m.r. spectra in deuterium oxide of nine primary, monodeoxyalditols from C, to C, have been recorded at 400 MHz and the shifts and coupling constants obtained by computer simulation. The shifts and 3J coupling constants were used to derive conformational information which supports previous results on acyclic polyols.There is a wealth of information in the solution n.m.r. spectra and conformation of acyclic polyols, having free' or 0substituted * hydroxy groups, but acyclic deoxypolyols have received little attenti~n.'~,~ In the present work, the spectra of nine primary, monodeoxyalditols in deuterium oxide were interpreted by computer simulation; some were still very complex at 400 MHz, and the resulting shifts and coupling constants were used for conformational analysis.

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Section: %mentioning

confidence: 99%

1H nuclear magnetic resonance spectra and conformations of deoxyalditols in deuterium oxide

Gillies¹,

Lewis²

1985

J. Chem. Soc., Perkin Trans. 2

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“…The unit cell formed at the potential minimum is given in Table 1. This cell is in most respects superior to that obtained using the potentials of Kitaigorodskii [S] or Williams [12]. However the actual values used are not of prime importance as long as a physically plausible model results.…”

Section: Intermolecular Potential Energymentioning

confidence: 77%

Surface Dynamics of Molecular Crystals. A Calculation for Naphthalene

Pawley

Chaplot

1980

Physica Status Solidi (b)

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A model for calculating the statics and dynamics of a surface of a molecular crystal is presented.The (001) surface of naphthalene is chosen. The potential function used is the 6-exp non-bonded atom-atom function, which has gained success in lattice dynamics. Surface layers of different thicknesses are investigated, all indicating that the third layer deep has a maximum binding energy. A slab of twelve layers thickness is used for the dynamics calculation, which shows clear evidence of surface modes. These are in general of lower freqiiencifs than the bulk modes. The frequency distributions presented are divided into translational and librational parts, showing more clearly the nature of the surface modes.Es wird ein Model1 zur Berechnung der Statik und Dynamik einer Oberflache eines Molekiilkristalls vorgeschlagen. Die (001)-0berflache von Naphthalen wird gewahlt. Die benutzte Potentialfuriktiori ist die 6-exp nichtbindende Atom-Atom-Funktion, die sich a19 erfolgreich in der Gitterdynamik erwiesen hat. Oberflachenschichten verschiedener Dicke werden untersncht, die alle zeigen, daB die dritte Schichttiefe eine maximale Bindungsenergie besitzt. Xin Block von zwolf Schichten Dicke wird fur die Dynamikberechnungen benutzt, die einen klaren Hinweis auf Oberflachenmoden liefern. Diese haben im allgemeinen niedrigere Frequenzen als die Volumenmoden. Die vorgeschlagenen Frequenzverteilungen werden in Translations-und Librationsanteile zerlegt, die die Natur der Oberflachenmoden deutlicher zeigen.

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“…3-Amino-3-deoxy-D-glucose (GSA-3) was synthesized from D-glucose in seven steps (Figure 1) using the methods previously reported (12)(13)(14)(15)(16)(17)(18). Hydroxyl groups were protected using the method of Blakley et al (12) 6-Amino-6-deoxy-R-D-methylglucoside (GSA-6).…”

Section: Chemicalsmentioning

confidence: 99%

Synthesis and Antibacterial Activity of Aminodeoxyglucose Derivatives against Listeria innocua and Salmonella typhimurium

Muhizi¹,

Grelier²,

Coma³

2009

J. Agric. Food Chem.

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In this study aminodeoxyglucose derivatives were synthesized and evaluated for their antibacterial activity against two food bacteria, Listeria innocua and Salmonella typhimurium . 6-Amino-6-deoxy-alpha-D-methylglucopyranose (GSA-6), 3-amino-3-deoxy-D-glucopyranoside (GSA-3), and beta-D-glucopyranosylamine (GSA-1) were synthesized and concurrently tested with commercially available D-glucosamine (GSA-2) for antibacterial activity. Results obtained from this study showed a pronounced antagonist effect due to the position of amino groups of aminoglucose derivatives on the antibacterial activity. GSA-3 was the most active compound. At a concentration of 2 x 10(-4) mol mL(-1), it delayed the growth of both bacteria with percentages of inhibition of 29 and 15% for L. innocua and S. typhimurium, respectively. At the same concentration the percentages of inhibition for other aminodeoxyglucoses varied between 5 and 18% and between 2 and 11% for L. innocua and S. typhimurium, respectively. All compounds were characterized by FTIR, (1)H NMR, and (13)C NMR spectroscopy.

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A new synthesis of 3-acetamido-3-deoxy-d-glucose

Abstract: A new synthesis of 3-acetamido-3-deoxy-d-glucose (kanosamine) has been devised, involving the replacement by azide ion, with inversion, of the sulfonate group in 1,2;5,6-di-O-isopropylidene-3-O-p-tolylsulfonyl-d-allofuranose.

Cited by 30 publications

References 0 publications

1H nuclear magnetic resonance spectra and conformations of deoxyalditols in deuterium oxide

1H nuclear magnetic resonance spectra and conformations of deoxyalditols in deuterium oxide

Surface Dynamics of Molecular Crystals. A Calculation for Naphthalene

Synthesis and Antibacterial Activity of Aminodeoxyglucose Derivatives against Listeria innocua and Salmonella typhimurium

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