Abstract:
Competitive glycosylation experiments with a galactofuranosyl trichloroacetimidate donor were performed with glucosamine acceptors having a free 4-OH group and carrying different protecting groups at N-2, O-3, and O-6. The most reactive acceptor is the N-dimethylmaleimido 3,6-di-O-benzylated derivative (6c), which reacts even faster than the oxazolidinone 1a. Molecular orbital calculations have helped to rationalize these experimental facts in terms of a hard-hard reaction occurring between the donor and the acceptor. © 2006 Elsevier Ltd. All rights reserved.
Registro:
| Documento: |
Artículo
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| Título: | A comparative study of the influence of some protecting groups on the reactivity of d-glucosamine acceptors with a galactofuranosyl donor |
| Autor: | Bohn, M.L.; Colombo, M.I.; Stortz, C.A.; Rúveda, E.A. |
| Filiación: | Instituto de Química Orgánica y de Síntesis (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Suipacha 531, 2000 Rosario, Argentina
Departamento de Química Orgánica-CIHIDECAR, Facultad de Ciencias Exactas y Naturales, UBA, Ciudad Universitaria, Pab. 2, 1428 Buenos Aires, Argentina
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| Palabras clave: | Competitive glycosylations; DFT; Galactofuranosyl donor; Glucosamine acceptors; N-Dimethylmaleoyl group; Conformations; Glucose; Molecular dynamics; Numerical methods; Probability density function; Reaction kinetics; Competitive glycosylations; Galactofuranosyl donors; Glucosamine acceptors; N-Dimethylmaleoyl groups; Amines; furan derivative; glucosamine; hydroxyl group; oxazolidinone derivative; trichloroacetimidic acid; article; calculation; conjugation; donor; glycosylation; priority journal; protection; reaction analysis; synthesis; Galactose; Glucosamine; Glycosylation |
| Año: | 2006
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| Volumen: | 341
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| Número: | 9
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| Página de inicio: | 1096
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| Página de fin: | 1104
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| DOI: |
http://dx.doi.org/10.1016/j.carres.2006.03.030 |
| Título revista: | Carbohydrate Research
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| Título revista abreviado: | Carbohydr. Res.
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| ISSN: | 00086215
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| CODEN: | CRBRA
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| CAS: | glucosamine, 3416-24-8, 4607-22-1; Galactose, 26566-61-0; Glucosamine, 3416-24-8
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| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v341_n9_p1096_Bohn |
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Citas:
---------- APA ----------
Bohn, M.L., Colombo, M.I., Stortz, C.A. & Rúveda, E.A.
(2006)
. A comparative study of the influence of some protecting groups on the reactivity of d-glucosamine acceptors with a galactofuranosyl donor. Carbohydrate Research, 341(9), 1096-1104.
http://dx.doi.org/10.1016/j.carres.2006.03.030---------- CHICAGO ----------
Bohn, M.L., Colombo, M.I., Stortz, C.A., Rúveda, E.A.
"A comparative study of the influence of some protecting groups on the reactivity of d-glucosamine acceptors with a galactofuranosyl donor"
. Carbohydrate Research 341, no. 9
(2006) : 1096-1104.
http://dx.doi.org/10.1016/j.carres.2006.03.030---------- MLA ----------
Bohn, M.L., Colombo, M.I., Stortz, C.A., Rúveda, E.A.
"A comparative study of the influence of some protecting groups on the reactivity of d-glucosamine acceptors with a galactofuranosyl donor"
. Carbohydrate Research, vol. 341, no. 9, 2006, pp. 1096-1104.
http://dx.doi.org/10.1016/j.carres.2006.03.030---------- VANCOUVER ----------
Bohn, M.L., Colombo, M.I., Stortz, C.A., Rúveda, E.A. A comparative study of the influence of some protecting groups on the reactivity of d-glucosamine acceptors with a galactofuranosyl donor. Carbohydr. Res. 2006;341(9):1096-1104.
http://dx.doi.org/10.1016/j.carres.2006.03.030
