Navegar

Colección

Datos Estadísticas

Artículo

La versión final de este artículo es de uso interno. El editor solo permite incluir en el repositorio el artículo en su versión post-print. Por favor, si usted la posee enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

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
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
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
Volumen:341
Número:9
Página de inicio:1096
Página de fin:1104
DOI: http://dx.doi.org/10.1016/j.carres.2006.03.030
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:glucosamine, 3416-24-8, 4607-22-1; Galactose, 26566-61-0; Glucosamine, 3416-24-8
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v341_n9_p1096_Bohn

Referencias:

  • Davis, B.G., (2002) Chem. Rev., 102, pp. 579-601
  • Paulsen, H., (1982) Angew. Chem., Int. Ed. Engl, 21, pp. 155-224
  • Crich, D., Dudkin, V., (2001) J. Am. Chem. Soc., 123, pp. 6819-6825
  • Liao, L., Auzanneau, F.-I., (2005) J. Org. Chem., 70, pp. 6265-6273
  • Paz, J.-L., Ojeda, R., Barrientos, A.G., Penadés, S., Martín Lomas, M., (2005) Tetrahedron: Asymmetry, 16, pp. 149-158
  • Debenham, J., Rodebaugh, R., Fraser Reid, B., (1997) Liebigs Ann./Recl., pp. 791-809
  • Xue, J., Khaja, S.D., Locke, R.D., Matta, K.L., (2004) Synlett, pp. 861-865
  • Debenham, J.S., Fraser Reid, B., (1996) J. Org. Chem., 61, pp. 432-433
  • Dudkin, V.Y., Miller, J.S., Danishefsky, S.J., (2003) Tetrahedron Lett., 44, pp. 1791-1793
  • Crich, D., Vinod, A.U., (2005) J. Org. Chem., 70, pp. 1291-1296
  • Wang, H., Ning, J., (2003) J. Org. Chem., 68, pp. 2521-2524
  • Gallo-Rodriguez, C., Gandolfi, L., Lederkremer, R.M., (1999) Org. Lett., 1, pp. 245-247
  • Lederkremer, R.M., Colli, W., (1995) Glycobiology, 5, pp. 547-552
  • Gallo-Rodriguez, C., Varela, O., Lederkremer, R.M., (1996) J. Org. Chem., 61, pp. 1886-1889
  • Gallo-Rodriguez, C., Gil-Libarona, M.A., Mendoza, V.M., Lederkremer, R.M., (2002) Tetrahedron, 58, pp. 9373-9380
  • Aly, M.R.E., Castro-Palomino, J.C., Ibrahim, E.-S.I., El-Ashary, E.-S.H., Schmidt, R.R., (1998) Eur. J. Org. Chem., pp. 2305-2316
  • Wilder, R., Mobashery, S., (1992) J. Org. Chem., 57, pp. 2755-2756
  • Berkin, A., Szarek, M.A., Phenkiewicz, J., Szarek, W.A., Kisilevsky, R., (2000) Carbohydr. Res., 325, pp. 30-45
  • Hesek, D., Lee, M., Morio, K., Mobashery, S., (2004) J. Org. Chem., 69, pp. 2137-2146
  • Tsvetkov, Y.E., Nikolaev, A.V., (2000) J. Chem. Soc., Perkin Trans. 1, pp. 889-891
  • Cid, M.B., Alfonso, F., Martín Lomas, M., (2005) Synlett, pp. 2052-2056. , and references cited therein
  • Csonka, G.I., (2002) J. Mol. Struct. (THEOCHEM), 584, pp. 1-4
  • Magaud, D., Dolmazon, R., Anker, D., Doutheau, A., Dory, Y.L., Deslongchamps, P., (2000) Org. Lett., 2, pp. 2275-2277
  • Parr, R.G., Yang, W., (1984) J. Am. Chem. Soc., 106, pp. 4049-4050
  • Berkowitz, M., (1987) J. Am. Chem. Soc., 109, pp. 4823-4825
  • Li, Y., Evans, J.N.S., (1995) J. Am. Chem. Soc., 117, pp. 7756-7759
  • Yang, W., Mortier, W.J., (1986) J. Am. Chem. Soc., 108, pp. 5708-5711
  • Contreras, R.R., Fuentealba, P., Galván, M., Pérez, P., (1999) Chem. Phys. Lett., 304, pp. 405-413
  • Chattaraj, P.K., (2001) J. Phys. Chem. A, 105, pp. 511-513
  • Besler, B.H., Merz Jr., K.M., Kollman, P.A., (1990) J. Comput. Chem., 11, pp. 431-439
  • Chirlian, L.E., Francl, M.M., (1987) J. Comput. Chem., 8, pp. 894-905
  • Breneman, C.M., Wiberg, K.B., (1990) J. Comput. Chem., 11, pp. 361-373
  • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Pople, J.A., (1998) Gaussian 98, Revision A.7, , Gaussian, Pittsburgh, PA
  • Allinger, N.L., Yuh, Y.H., Lii, J.-H., (1989) J. Am. Chem. Soc., 111, pp. 8551-8566
  • Dewar, M.J.S., Zoebich, E.G., Healy, E.F., Stewart, J.J.P., (1985) J. Am. Chem. Soc., 107, pp. 3902-3909
  • Pérez, P., Toro-Labbé, A., Aizman, A., Contreras, R., (2002) J. Org. Chem., 67, pp. 4747-4752

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