Navegar

Colección

Datos Estadísticas

Artículo

El editor solo permite decargar el artículo en su versión post-print desde el repositorio. Por favor, si usted posee dicha versión, enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Two simple procedures for the synthesis of 2-deoxy-D-lyxo-hexono-1,4-lactone are described. Reductive cleavage of a 2-O-tosyl derivative of D-galactono-1,4-lactone in the presence of sodium iodide afforded the 2-deoxy derivative. On the other hand, α-deoxygenation of D-galactono-1,4-lactone was easily achieved by photochemical electron transfer deoxygenation of HO-2 as the 3-(trifluoromethyl)benzoate. Methyl 2-deoxy-β-D-lyxo-hexafuranoside ('methyl 2-deoxy-β-D-galactofuranoside') was synthesized and tested as substrate for exo β-D-galactofuranosidase from Penicillium fellutanum. The reaction was followed by HPAEC, showing that methyl 2-deoxy-β-D-galactofuranoside was not hydrolyzed by incubation with the enzyme. Neither the 2-deoxy lactone, nor the 2-deoxy-β-D-galactofuranoside acted as inhibitors of the reaction with the 4-nitrophenyl β-D-galactofuranoside. The present and our previous results show that the hydroxyl groups at C-2, C-3 and C-6 of the galactofuranoside are essential for interaction with the exo β-D-galactofuranosidase. © 2002 Elsevier Science Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Photoinduced electron transfer and chemical α-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides
Autor:Chiocconi, A.; Marino, C.; Otal, E.; De Lederkremer, R.M.
Filiación:CIHIDECAR, Departamento De Química Orgánica, Universidad De Buenos Aires, Pabellon II, Ciudad Univ., 1428 Buenos Aires, Argentina
Palabras clave:2-Deoxy-D-lyxo- hexono-1,4-lactone; 2-Deoxy-D-lyxo-hexofuranosides; Deoxy sugars; Exo β-D-Galactofuranosidase; Electrons; Enzymes; Hydrolysis; Photochemical reactions; Sodium compounds; Synthesis (chemical); Electron transfer; Carbohydrates; benzoic acid derivative; carbohydrate derivative; dextro galactono 1,4 lactone; lactone derivative; methyl 2 deoxy beta dextro lyxohexafuranoside; sodium iodide; unclassified drug; article; carbohydrate synthesis; chemical reaction; degradation; electron transport; hydrolysis; oxygenation; Penicillium; photochemistry; priority journal; reduction; beta-Galactosidase; Chromatography, High Pressure Liquid; Electrons; Galactose; Glycoside Hydrolases; Magnetic Resonance Spectroscopy; Penicillium; Photochemistry; Structure-Activity Relationship; Sugar Acids; Penicillium fellutanum
Año:2002
Volumen:337
Número:21-23
Página de inicio:2119
Página de fin:2126
DOI: http://dx.doi.org/10.1016/S0008-6215(02)00118-0
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CAS:2-deoxy-lyxo-hexose, 6664-99-9; beta-Galactosidase, EC 3.2.1.23; exo-beta-D-galactofuranosidase, EC 3.2.1.-; galactonolactone, 2426-46-2; Galactose, 26566-61-0; Glycoside Hydrolases, EC 3.2.1.-; Sugar Acids
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v337_n21-23_p2119_Chiocconi

Referencias:

  • Lederkremer, R.M., Colli, W., (1995) Glycobiology, 5, pp. 547-552
  • Rietschel-Berst, M., Jentoft, N.H., Rick, P.D., Pletcher, C., Fang, F., Gander, J.E., (1977) J. Biol. Chem., 252, pp. 3219-3226
  • Tuekam, B.A., Park, Y.-I., Unkefer, C.J., Gander, J.E., (2001) Appl. Envirom. Microbiol., 67, pp. 4648-4656
  • Varela, O., Marino, C., Lederkremer, R.M., (1986) Carbohydr. Res., 155, pp. 247-251
  • Marino, C., Cancio, M.J., Varela, O., Lederkremer, R.M., (1995) Carbohydr. Res., 276, pp. 209-213
  • Marino, C., Mariño, K., Miletti, L., Manso Alves, M.J., Colli, W., Lederkremer, R.M., (1998) Glycobiology, 8, pp. 901-904
  • Marino, C., Herczegh, P., Lederkremer, R.M., (2001) Carbohydr. Res., 333, pp. 123-128
  • Mariño, K., Lima, C., Maldonado, S., Marino, C., Lederkremer, R.M., (2002) Carbohydr. Res., 337, pp. 891-897
  • Miletti, L.C., Marino, C., Mariño, K., Lederkremer, R.M., Colli, W., Manso Alves, M.J., (1999) Carbohydr. Res., 320, pp. 176-182
  • Marino, C., Chiocconi, A., Varela, O., Lederkremer, R.M., (1998) Carbohydr. Res., 311, pp. 183-189
  • Chiocconi, A., Marino, C., Lederkremer, R.M., (2000) Carbohydr. Res., 323, pp. 7-13
  • Lerner, L.M., (1972) Methods Carbohydr. Chem., 6, pp. 131-134
  • Bock, K., Adelhorst, K., (1990) Carbohydr. Res., 202, pp. 131-149
  • D'Accorso, N.B., Thiel, I.M.E., Schüller, M., (1983) Carbohydr. Res., 124, pp. 177-184
  • Lederkremer, R.M., Marino, C., Varela, O., (1990) Carbohydr. Res., 200, pp. 227-235
  • Fleet, G.W.J., Son, J.C., (1988) Tetrahedron, 44, pp. 2637-2647
  • Paulsen, H., Eberstein, K., (1976) Chem. Ber., 109, pp. 3907-3914
  • Marino, C., Varela, O., Lederkremer, R.M., (1991) Carbohydr. Res., 220, pp. 145-153
  • Saito, I., Ikehira, H., Kasatani, R., Watanabe, M., Matsuura, T., (1986) J. Am. Chem. Soc., 108, pp. 3115-3117
  • Wang, Z., Prudhomme, D.R., Buck, J.R., Minnied, P., Rizzo, C., (2000) J. Org. Chem., 65, pp. 5969-5985. , and references cited therein
  • Riedel, S., Donnerstag, A., Hennig, L., Welzel, P., Richter, J., Hobert, K., Müller, D., Van Heijenoort, J., (1999) Tetrahedron, 55, pp. 1921-1936
  • Bock, K., Lundt, I., Pedersen, C., (1984) Acta Chem. Scand. B, 38, pp. 555-561
  • Overend, W.G., Shafizadeh, F., Stacey, M., (1950) J. Chem. Soc., pp. 671-677
  • Marino, C., Varela, O., Lederkremer, R.M., (1989) Carbohydr. Res., 190, pp. 65-76
  • Hakamata, W., Nishio, T., Oku, T., (2000) Carbohydr. Res., 324, pp. 107-115

Citas:

---------- APA ----------
Chiocconi, A., Marino, C., Otal, E. & De Lederkremer, R.M. (2002) . Photoinduced electron transfer and chemical α-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides. Carbohydrate Research, 337(21-23), 2119-2126.
http://dx.doi.org/10.1016/S0008-6215(02)00118-0
---------- CHICAGO ----------
Chiocconi, A., Marino, C., Otal, E., De Lederkremer, R.M. "Photoinduced electron transfer and chemical α-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides" . Carbohydrate Research 337, no. 21-23 (2002) : 2119-2126.
http://dx.doi.org/10.1016/S0008-6215(02)00118-0
---------- MLA ----------
Chiocconi, A., Marino, C., Otal, E., De Lederkremer, R.M. "Photoinduced electron transfer and chemical α-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides" . Carbohydrate Research, vol. 337, no. 21-23, 2002, pp. 2119-2126.
http://dx.doi.org/10.1016/S0008-6215(02)00118-0
---------- VANCOUVER ----------
Chiocconi, A., Marino, C., Otal, E., De Lederkremer, R.M. Photoinduced electron transfer and chemical α-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides. Carbohydr. Res. 2002;337(21-23):2119-2126.
http://dx.doi.org/10.1016/S0008-6215(02)00118-0