1H- and 13C-n.m.r. assignments and conformational analysis of some monosaccharide and oligosaccharide substrate-analogues of lysozyme

Boyd, Jonathan; Porteous, Rod; Soffe, Nick; Delepierre, Muriel

doi:10.1016/0008-6215(85)90004-7

Cited by 25 publications

(6 citation statements)

References 27 publications

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“…Thus ga means that O6 is gauche to O5 and anti to C4. All the experimental data in solution , and in the solid phase are consistent with the predominance of the gg form. However, NMR measurements of glucose found considerable amounts of the ga form as well ( gg:ga:ag ratios of 56:44:0 and 53:45:2 for the α and β anomers, respectively) …”

Section: Anomeric Free Energies Of Pyranosessupporting

confidence: 69%

Carbohydrates: United Atom AMBER* Parameterization of Pyranoses and Simulations Yielding Anomeric Free Energies

1996

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The success of molecular modeling using classical potential functions (i.e force field calculations) rests heavily on the availability of specific, high-quality parameters that accurately describe the gas phase potential surface of the molecular system under study, on solvent models that reliably reproduce the effect of the medium, and on simulation methods that sample all significantly populated conformations of the entire system with the correct statistical weights. In this paper we present a set of molecular mechanics parameters that were developed using ab initio molecular orbital calculations to model pyranoses in the context of the AMBER* force field in the molecular modeling package MacroModel 5.0. These parameters were tailored to reproduce the quantum mechanical conformational energies of certain small molecules that were taken as models for common substructures in monosaccharides. Solvent was included as the GB/SA continuum model for water. The sampling problem was solved for these systems using the recently described MC(JBW)/SD simulation method that facilitates interconversion of predetermined conformational minima by alternating between smart Monte Carlo and stochastic dynamics steps. A series of such MC(JBW)/SD simulations using the new carbohydrate parameters was used to calculate anomeric α,β ratios (and thus anomeric free energy differences) for tetrahydropyran derivatives and the pyranose monosaccharides glucose, methyl glucoside, mannose, methyl mannoside, galactose, 2-deoxyglucose, and N-acetylglucosamine. In all cases, the simulations converged within 1 ns to yield anomeric free energies that are within 0.4 kcal/mol of the experimentally determined anomeric free energies in water.

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Section: Anomeric Free Energies Of Pyranosessupporting

confidence: 69%

Carbohydrates: United Atom AMBER* Parameterization of Pyranoses and Simulations Yielding Anomeric Free Energies

1996

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“…10). (41). Sequence analysis, obtained from the gHMBC experiment, showed that all the units are β1-3 linked except for the non-reducing terminal GlcNAc residue which is β1-4 linked with the D unit and for the A residue which is β1-6 linked with the reducing-end residue.…”

Section: Fraction Chsn II : Linkage Between Chitin and Glucanmentioning

confidence: 98%

Molecular Organization of the Alkali-insoluble Fraction ofAspergillus fumigatus Cell Wall

Fontaine¹,

Simenel²,

Dubreucq³

et al. 2000

Journal of Biological Chemistry

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372

284

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Physical and biological properties of the fungal cell wall are determined by the composition and arrangement of the structural polysaccharides. Cell wall polymers of fungi are classically divided into two groups depending on their solubility in hot alkali. We have analyzed the alkali-insoluble fraction of the Aspergillus fumigatus cell wall, which is the fraction believed to be responsible for fungal cell wall rigidity. Using enzymatic digestions with recombinant endo-beta-1,3-glucanase and chitinase, fractionation by gel filtration, affinity chromatography with immobilized lectins, and high performance liquid chromatography, several fractions that contained specific interpolysaccharide covalent linkages were isolated. Unique features of the A. fumigatus cell wall are (i) the absence of beta-1,6-glucan and (ii) the presence of a linear beta-1, 3/1,4-glucan, never previously described in fungi. Galactomannan, chitin, and beta-1,3-glucan were also found in the alkali-insoluble fraction. The beta-1,3-glucan is a branched polymer with 4% of beta-1,6 branch points. Chitin, galactomannan, and the linear beta-1, 3/1,4-glucan were covalently linked to the nonreducing end of beta-1, 3-glucan side chains. As in Saccharomyces cerevisiae, chitin was linked via a beta-1,4 linkage to beta-1,3-glucan. The data obtained suggested that the branching of beta-1,3-glucan is an early event in the construction of the cell wall, resulting in an increase of potential acceptor sites for chitin, galactomannan, and the linear beta-1,3/1,4-glucan.

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“…(2a) Amorphous solid; 1 O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-2-deoxy-D-gluco-pyranose (N,N′-diacetylchitobiose) (4) was prepared from colloidal chitin by enzymatic (chiti-nase; EC 3.2.1.14) degradation. The preparation was carried out in the same way as reported by Kuzuhara and colleagues (8,9,11) and Boyd et al (10).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and characterization of novel amphiphiles containing amino acid and carbohydrate

Abe

Asakura

Osanai

2004

J Surfact & Detergents

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Amphiphiles composed of two different natural renewable raw materials, amino acid and carbohydrate (chitin), were synthesized, and their colloidal properties were studied. N-Higher acylated glutamic and aspartic acid were used as amino acid raw materials. Chitin monomer (N-acetyl glucosamine) and dimer (N,N′-diacetylchitobiose) were employed as the carbohydrate hydrophilic moiety in the amphiphiles. These surfactants showed a surface tension in the range of 30-36 mN/m at their critical micelle concentration. In the study of colloidal properties, such as surface tension, emulsification, and foaming, the surfactants containing the monosaccharide hydrophilic group showed much better results than those with disaccharide. Biodegradation measurements showed that the tested surfactants are biodegraded by environmental microorganisms to 57-73% of the initial levels in 14 d. Their biodegradation extent depended on neither the saccharide structure nor the kind of amino acid.

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1H- and 13C-n.m.r. assignments and conformational analysis of some monosaccharide and oligosaccharide substrate-analogues of lysozyme

Cited by 25 publications

References 27 publications

Carbohydrates: United Atom AMBER* Parameterization of Pyranoses and Simulations Yielding Anomeric Free Energies

Carbohydrates: United Atom AMBER* Parameterization of Pyranoses and Simulations Yielding Anomeric Free Energies

Molecular Organization of the Alkali-insoluble Fraction ofAspergillus fumigatus Cell Wall

Synthesis and characterization of novel amphiphiles containing amino acid and carbohydrate

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