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Abstract:

The crystal structure of methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido- α-d-allopyranoside was solved in order to gain insight into the hydrogen bond features which can be determining features in the glycosylation regioselectivity observed for this compound. An intramolecular hydrogen bond between the hydroxyl H(O)3 and a carbonyl oxygen from the dimethylmaleoyl (DMM) group was observed. This was in agreement with previous NMR temperature shift determinations and molecular modeling. The determination has also found an intermolecular hydrogen bond between the second hydroxyl H(O)4 and the other carbonyl oxygen (generated by symmetry) from DMM. The crystal structure was optimized by five different functionals, namely the hybrid methods B3LYP, M06-2X, B3PW91, and PBE0, and the pure functional PBE, and the optimized geometries were compared with the crystal geometry and with MM3. An excellent coincidence of the geometries was found with the five quantum methods, with minor details deviating from this coincidence. PBE tends to yield larger bond distances, whereas M06-2X fails slightly to match the exocyclic torsion angles for the sugar moiety. In any case, the differences are small, implying that any of these functionals can accurately emulate the geometries of a complex carbohydrate derivative like this one. © 2012 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Structural analysis of methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido- α-D-allopyranoside by X-ray crystallography, NMR, and QM calculations: Hydrogen bonding and comparison of density functionals
Autor:Colombo, M.I.; Rúveda, E.A.; Gorlova, O.; Lalancette, R.; Stortz, C.A.
Filiación:Instituto de Química Rosario (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Suipacha 531, 2000 Rosario, Argentina
Carl A. Olson Memorial Laboratories, Department of Chemistry, Rutgers University, Newark, NJ 07102, United States
Departamento de Química Orgánica-CIHIDECAR, FCEyN-Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:Allosamine; Conformation; Crystal structure; Density functional theory; N-Dimethylmaleloyl group; Allosamine; Bond distance; Carbonyl oxygen; Complex carbohydrates; Crystal geometry; Density functionals; Functionals; Gain insight; Hybrid method; Intermolecular hydrogen bonds; Intramolecular hydrogen bond; N-Dimethylmaleloyl group; Optimized geometries; Quantum methods; Sugar moiety; Temperature shift; Torsion angle; Carbohydrates; Complexation; Conformations; Crystal structure; Density functional theory; Geometry; Optimization; Oxygen; X ray crystallography; Hydrogen bonds; 6 o benzyl 2 deoxy 2 dimethylmaleimido alpha dextro allopyranoside; carbohydrate derivative; carbonyl derivative; dimethylmaleoyl; hydroxyl group; oxygen; sugar; unclassified drug; article; chemical structure; density functional theory; geometry; hydrogen bond; molecular model; priority journal; quantum mechanics; X ray crystallography; Crystallography, X-Ray; Glycosides; Hydrogen Bonding; Magnetic Resonance Spectroscopy; Molecular Structure
Año:2012
Volumen:353
Página de inicio:79
Página de fin:85
DOI: http://dx.doi.org/10.1016/j.carres.2012.03.025
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:oxygen, 7782-44-7; Glycosides
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v353_n_p79_Colombo

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Citas:

---------- APA ----------
Colombo, M.I., Rúveda, E.A., Gorlova, O., Lalancette, R. & Stortz, C.A. (2012) . Structural analysis of methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido- α-D-allopyranoside by X-ray crystallography, NMR, and QM calculations: Hydrogen bonding and comparison of density functionals. Carbohydrate Research, 353, 79-85.
http://dx.doi.org/10.1016/j.carres.2012.03.025
---------- CHICAGO ----------
Colombo, M.I., Rúveda, E.A., Gorlova, O., Lalancette, R., Stortz, C.A. "Structural analysis of methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido- α-D-allopyranoside by X-ray crystallography, NMR, and QM calculations: Hydrogen bonding and comparison of density functionals" . Carbohydrate Research 353 (2012) : 79-85.
http://dx.doi.org/10.1016/j.carres.2012.03.025
---------- MLA ----------
Colombo, M.I., Rúveda, E.A., Gorlova, O., Lalancette, R., Stortz, C.A. "Structural analysis of methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido- α-D-allopyranoside by X-ray crystallography, NMR, and QM calculations: Hydrogen bonding and comparison of density functionals" . Carbohydrate Research, vol. 353, 2012, pp. 79-85.
http://dx.doi.org/10.1016/j.carres.2012.03.025
---------- VANCOUVER ----------
Colombo, M.I., Rúveda, E.A., Gorlova, O., Lalancette, R., Stortz, C.A. Structural analysis of methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido- α-D-allopyranoside by X-ray crystallography, NMR, and QM calculations: Hydrogen bonding and comparison of density functionals. Carbohydr. Res. 2012;353:79-85.
http://dx.doi.org/10.1016/j.carres.2012.03.025