Combining Computational Chemistry and Crystallography for a Better Understanding of the Structure of Cellulose

French, Alfred D.

doi:10.1016/b978-0-12-396527-1.00002-4

Cited by 29 publications

(16 citation statements)

References 176 publications

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“…The numbering of the cellulose chains is as given in Fig. 7 angles in regenerated cellulose crystals and reported that they fell in the range: -90°to -97°for U and -141°to -149°for W. These angles were also close to those of the minimum energy crystal structure located on the U/W contour map (Schnupf and Momany 2011;French 2012). The cellulose-chains in the oil-in-water system adopted predominantly similar conformations, leading to a flat and plane-like chain structure.…”

Section: Conformations Of Cellulose Chains In Oil-in-water Systemsmentioning

confidence: 76%

Molecular dynamics simulation of cellulose-coated oil-in-water emulsions

et al. 2017

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The behaviors of cellulose chains and cellulose mini-crystal in oil-in-water emulsions were studied by molecular dynamics simulations to investigate the coating states and the structural features of cellulose in these emulsions. In oil-in-water emulsion, dispersed cellulose chains gradually assemble during the progress of the simulation, eventually surrounding the octane droplet. In case of a cellulose mini-crystal, the cellulose chain at the corner of the crystal first contacts with the octane droplet through its hydrophobic surface. The other cellulose chains along the crystal plane then gradually move toward the octane molecules. In both emulsions, the cellulose was found to interact with both water and octane surfaces with specific conformations that allow the CH groups of the glucose rings to contact with octane molecules, while the OH groups of these rings contact with water molecules to form hydrogen bonds. The cellulose chains on the octane droplet also contact with each other through lateral hydrogen bonding between chains. These interactions stabilize the emulsion formed by cellulose molecules as surfactants.

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Section: Conformations Of Cellulose Chains In Oil-in-water Systemsmentioning

confidence: 76%

Molecular dynamics simulation of cellulose-coated oil-in-water emulsions

et al. 2017

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“…For the compounds GalbNHSO 2 CH 3 (18) and GalbNHSO 2 CH 2 Cl (31), in which the C4-OH group is in an axial position, the hydroxymethyl group adopts a gt conformation with the torsion angles, w, close to 638 and w around À1758. In the case of CellbNHSO 2 CH 3 (22), however, the two conformers A and B differ in the conformation of the hydroxymethyl group. The hydroxymethyl group in conformer A adopts a gg conformation in both the reducing end residue as well as the non-reducing…”

Section: X-ray Crystallographic Investigationmentioning

confidence: 97%

“…The ORTEP representations of their solved structures with atom numbering are shown in Figure 3. All the N-(b-d-glycosyl)methanesulfonamides (17,19,22, and 23) crystallized in the monoclinic crystal system with a P2 1 space group except for N-(b-d-galactopyranosyl)methanesulfonamide (18), which crystallized in the C2 space group. GalbNHSO 2 CH 3 (18), GlcNAcbNHSO 2 CH 3 (19), and LacbNHSO 2 CH 3 (23) crystallized as monohydrates, whereas GlcbNHSO 2 CH 3 (17) and Figure 3).…”

Section: X-ray Crystallographic Investigationmentioning

confidence: 99%

“…Geometrical parameters for all the crystals are compared with the series as well as with those already reported for alkanamido derivatives. Two different conformers were present in the asymmetric unit of CellbNHSO 2 CH 3 (22) labeled as A and B.…”

Section: X-ray Crystallographic Investigationmentioning

confidence: 99%

“…[20] Parameter (23), and GalbNHSO 2 CH 2 Cl (31), as seen in most of the b-1-N-alkan-A C H T U N G T R E N N U N G amido sugar derivatives, whereas the reverse was true for GlcNAcbNHSO 2 CH 2 Cl (32). In the case of conformer A of CellbNHSO 2 CH 3 (22), the C5 À O5 bond is longer than the C1 À O5 bond (in both the non-reducing end residue and reducing end residue) but both the bond lengths (C1 À O5 and C5 À O5) were equal in the case of the reducing end residue of conformer B. The CÀN bond lengths (C1ÀN1) for all the compounds 17-19, 22, 23, 31, and 32 were 1.41-1.44 in good agreement with the value of 1.44 observed for GlcNAcbAsn.…”

Section: X-ray Crystallographic Investigationmentioning

confidence: 99%

See 2 more Smart Citations

Exploring the Effect of Bioisosteric Replacement of Carboxamide by a Sulfonamide Moiety on N‐Glycosidic Torsions and Molecular Assembly: Synthesis and X‐ray Crystallographic Investigation of N‐(β‐D‐Glycosyl)sulfonamides as N‐Glycoprotein Linkage Region Analogues

Srivastava

Varghese

Loganathan

2013

Chemistry A European J

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N-Glycoprotein linkage region constituents, 2-acetamido-2-deoxy-β-D-glucopyranose (GlcNAc) and asparagine (Asn) are conserved among all the eukaryotes. To gain a better understanding for nature's choice of GlcNAcβAsn as linkage region constituents and inter- and intramolecular carbohydrate-protein interactions, a detailed systemic structural study of the linkage region conformation is essential. Earlier crystallographic studies of several N-(β-glycopyranosyl)alkanamides showed that N-glycosidic torsion, φN , is influenced to a larger extent by structural variation in the sugar part than that of the aglycon moiety. To explore the effect of the bioisosteric replacement of a carboxamide group by a sulfonamide moiety on the N-glycosidic torsions as well as on molecular assembly, several glycosyl methanesulfonamides and glycosyl chloromethanesulfonamides were synthesized as analogues of the N-glycoprotein linkage region, and crystal structures of seven of these compounds have been solved. A comparative analysis of this series of crystal structures as well as with those of the corresponding alkanamido derivatives revealed that N-glycosidic torsion, φN, does not alter significantly. Methanesulfonamido and chloromethanesulfonamido derivatives of GlcNAc display a different aglycon conformation compared to other sulfonamido analogues. This may be due to the cumulative effect of the direct hydrogen bonding between N1 and O1' and C-H···O interactions of the aglycon chain, revealing the uniqueness of the GlcNAc as the linkage sugar.

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Escherichia coli β‐Galactosidase Inhibitors through Modifications at the Aglyconic Moiety: Experimental Evidence of Conformational Distortion in the Molecular Recognition Process

Calle

Roldós

Cañada

et al. 2013

Chemistry A European J

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Herein, we describe the use of thioglycosides as glycosidase inhibitors by employing novel modifications at the reducing end of these glycomimetics. The inhibitors display a basic galactopyranosyl unit (1→4)-bonded to a 3-deoxy-4-thiopentopyranose moiety. The molecular basis of the observed inhibition has been studied by using a combination of NMR spectroscopy and molecular modeling techniques. It is demonstrated that these molecules are not recognized by Escherichia coli β-galactosidase in their ground-state conformation, with a conformational selection process taking place. In fact, the observed conformational distortion depends on the chemical nature of the compounds and results from the rotation around the glycosidic linkage (variation of Φ or Ψ) or from the deformation of the six-membered ring of the pentopyranose. The bound conformations of the ligand are adapted in the enzymatic pocket with a variety of hydrogen-bond, van der Waals, and stacking interactions.

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Combining Computational Chemistry and Crystallography for a Better Understanding of the Structure of Cellulose

Cited by 29 publications

References 176 publications

Molecular dynamics simulation of cellulose-coated oil-in-water emulsions

Molecular dynamics simulation of cellulose-coated oil-in-water emulsions

Exploring the Effect of Bioisosteric Replacement of Carboxamide by a Sulfonamide Moiety on N‐Glycosidic Torsions and Molecular Assembly: Synthesis and X‐ray Crystallographic Investigation of N‐(β‐D‐Glycosyl)sulfonamides as N‐Glycoprotein Linkage Region Analogues

Escherichia coli β‐Galactosidase Inhibitors through Modifications at the Aglyconic Moiety: Experimental Evidence of Conformational Distortion in the Molecular Recognition Process

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