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Abstract:

Four isomeric N-dimethylmaleoyl 4,6-O-benzylidene-protected d-hexosamine acceptors (2, 3, 4, and 5) with all possible configurations at C-1 and C-3 (e.g., derived from d-glucosamine and d-allosamine) were prepared, and the assessment of their O-3 relative reactivity through competition experiments using the known per-O-acetylated d-galactopyranosyl trichloroacetimidate donor (15) was then carried out. The reactivities are in the order 4 ≫ 2 > 5 > 3. The analysis of the NMR spectra of 2-5 at different temperature and modeling experiments carried out on analogs of 2-5 (DFT) and on the acceptors themselves (MM) are coincident, and have helped to establish the stability of the different hydrogen bonds, and of the conformers which carry them. The whole results suggest that the electronic effects (hydrogen bonds) are required to explain the observed trend, in spite of the axial conformation of the most reactive hydroxyl group. The steric effects appear only when hydrogen bonds are weak. © 2011 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:A comparative study of the O-3 reactivity of isomeric N-dimethylmaleoyl- protected d-glucosamine and d-allosamine acceptors
Autor:Colombo, M.I.; Stortz, C.A.; Rúveda, E.A.
Filiación:Instituto de Química Rosario (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Suipacha 531, 2000 Rosario, Argentina
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, UBA, Ciudad Universitaria, Pab. 2, 1428, Buenos Aires, Argentina
Palabras clave:Competitive glycosylations; Galactopyranosyl donor; Glucosamine/allosamine acceptors; Molecular modeling; N-Dimethylmaleoyl group; Benzylidene; Comparative studies; Electronic effects; Galactopyranosyl donor; Glucosamine/allosamine acceptors; Glycosylations; Hydroxyl groups; N-Dimethylmaleoyl group; NMR spectrum; Relative reactivities; Steric effect; Experiments; Glucosamine; Hydrogen; Molecular modeling; Nuclear magnetic resonance spectroscopy; Hydrogen bonds; benzylidene derivative; dimethylmaleoyl 4,6 o benzylidene; glucosamine; hexosamine; hydroxyl group; ozone; trichloroacetimidic acid; unclassified drug; article; chemical structure; comparative study; hydrogen bond; isomer; nuclear magnetic resonance spectroscopy; priority journal; synthesis; temperature; Glucosamine; Glycosides; Hydrogen Bonding; Isomerism; Magnetic Resonance Spectroscopy; Molecular Structure
Año:2011
Volumen:346
Número:5
Página de inicio:569
Página de fin:576
DOI: http://dx.doi.org/10.1016/j.carres.2011.01.017
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:glucosamine, 3416-24-8, 4607-22-1; ozone, 10028-15-6; Glucosamine, 3416-24-8; Glycosides; allosamine
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v346_n5_p569_Colombo

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Citas:

---------- APA ----------
Colombo, M.I., Stortz, C.A. & Rúveda, E.A. (2011) . A comparative study of the O-3 reactivity of isomeric N-dimethylmaleoyl- protected d-glucosamine and d-allosamine acceptors. Carbohydrate Research, 346(5), 569-576.
http://dx.doi.org/10.1016/j.carres.2011.01.017
---------- CHICAGO ----------
Colombo, M.I., Stortz, C.A., Rúveda, E.A. "A comparative study of the O-3 reactivity of isomeric N-dimethylmaleoyl- protected d-glucosamine and d-allosamine acceptors" . Carbohydrate Research 346, no. 5 (2011) : 569-576.
http://dx.doi.org/10.1016/j.carres.2011.01.017
---------- MLA ----------
Colombo, M.I., Stortz, C.A., Rúveda, E.A. "A comparative study of the O-3 reactivity of isomeric N-dimethylmaleoyl- protected d-glucosamine and d-allosamine acceptors" . Carbohydrate Research, vol. 346, no. 5, 2011, pp. 569-576.
http://dx.doi.org/10.1016/j.carres.2011.01.017
---------- VANCOUVER ----------
Colombo, M.I., Stortz, C.A., Rúveda, E.A. A comparative study of the O-3 reactivity of isomeric N-dimethylmaleoyl- protected d-glucosamine and d-allosamine acceptors. Carbohydr. Res. 2011;346(5):569-576.
http://dx.doi.org/10.1016/j.carres.2011.01.017