Abstract:
Anionic derivatives of methyl β-laminarabioside, methyl β-laminaratrioside and methyl β-maltoside, substituted in the primary hydroxyl groups, were synthesized and characterized spectroscopically. Sulfated methyl laminara-oligosaccharides (DP≥5) were also prepared. These model compounds for conformational studies allow the comparison of the influence of different anionic substituents (sulfate, phosphate, succinate and carboxylate) on the β-(1→3) and α-(1→4) glycosidic bond.
Registro:
Documento: |
Artículo
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Título: | Synthesis of anionic derivatives of methyl laminara-oligosaccharides and methyl β-maltoside |
Autor: | Leit, S.; Fernández Cirelli, A. |
Filiación: | Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR), Departamento de Química Orgánica, Universidad de Buenos Aires, 1428, Buenos Aires, Argentina
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Año: | 1998
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Volumen: | 86
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Número: | 3-6
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Página de inicio: | 261
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Página de fin: | 269
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Título revista: | Anales des la Asociacion Quimica Argentina
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ISSN: | 03650375
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p261_Leit |
Referencias:
- Fernández Cirelli, A., Covian, J.A., Ohno, N., Adachi, Y., Yadomal, T., (1989) Carbohydr. Res., 190, p. 329
- Suzuki, T., Ohno, N., Adachi, Y., Fernández Cirelli, A., Covian, J.A., Yadomal, T., (1991) Pharmacobio-Dyn., 14, p. 256
- Katsuraya, K., Ikushima, N., Takahashi, N., Shoji, T., Nakashima, H., Yamamoto, N., Yoshida, T., Uryu, T., (1994) Carbohyd Res., 260, p. 51
- Gao, Y., Fukuda, A., Katsuraya, K., Kaneco, Y., Minuera, T., Nakashima, H., Uryu, T., (1997) Macromolecules, 30, p. 3224
- Wang, L., Sakari, N., Kuzuhara, H., (1991) Carbohydr. Res., 219, p. 133
- Thiem, J., Karl, H., (1979) Chem. Ber., 112, p. 1046
- Moradei, O., Leit, S., Du Mortier, C., Fernández Cirelli, A., Thiem, J., (1993) J. Carbohydr. Chemistry, 12, p. 13
- Inohue, K., Kawamoto, K., Nakajima, H., Kohno, M., Kadoya, S., Mizuno, D., (1983) Carbohydr. Res., 115, p. 199
- McNaught, A.D., (1997) Adv Carbohydr. Chem. Biochem., 52, p. 43
- Bax, A., G., D., (1988) J. Magn. Reson., 63, p. 355
- Terho, T., Hartiala, K., (1971) Analyt. Biochem., 41, p. 471
- Bocker, T., Lindhorst, T.K., Thiem, J., Vill, V., (1992) Carbohydr. Res, 230, p. 245
- Forrester, P.F., Lloyd, P.F., Stuart, C.H., (1976) Carbohydr. Res,., 49, p. 175
- Chaudhary, S.K., Hernández, O., (1979) Tetrahedron Lett., 2, p. 95
- Fukuzawa, A., Sato, H., Masamune, T., (1987) Tetrahedron Lett., 28, p. 4303
- Castro, M., Kovensky, J., Fernández Cirelli, A., (1997) Tetrahedron Lett., 38, p. 3995
- Duttom, G.G.S., Slessor, K.N., (1966) Can. J. Chem., 44, p. 1069
- Quigley, G.J., Sarko, A., Marchessault, R.H., (1970) J. Am. Chem. Soc, 92, p. 5834
- Russell, M., Raymond, E., Billington, D., (1992) Carbohydr. Res., 234, p. 263
- Vermeersch, J., Schacht, E., (1986) Makromol. Chem., 187, p. 125
- Millar, J.C., Oehlschlager, A.C., Wong, J.W., (1983) J. Org. Chem., 48, p. 4404
- Schimidhammer, H., Brossi, A., (1983) J. Org. Chem., 48, p. 1469
- Kanai, K., Sakamoto, I., Owaga, S., Suami, T., (1987) Bull. Chem. Soc. Jpn., 60, p. 1529
- Geen, H., Freeman, R., (1991) J. Magn. Reson., 93, p. 93
- Freeman, R., (1991) Chem. Rev., 91, p. 1397
Citas:
---------- APA ----------
Leit, S. & Fernández Cirelli, A.
(1998)
. Synthesis of anionic derivatives of methyl laminara-oligosaccharides and methyl β-maltoside. Anales des la Asociacion Quimica Argentina, 86(3-6), 261-269.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p261_Leit [ ]
---------- CHICAGO ----------
Leit, S., Fernández Cirelli, A.
"Synthesis of anionic derivatives of methyl laminara-oligosaccharides and methyl β-maltoside"
. Anales des la Asociacion Quimica Argentina 86, no. 3-6
(1998) : 261-269.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p261_Leit [ ]
---------- MLA ----------
Leit, S., Fernández Cirelli, A.
"Synthesis of anionic derivatives of methyl laminara-oligosaccharides and methyl β-maltoside"
. Anales des la Asociacion Quimica Argentina, vol. 86, no. 3-6, 1998, pp. 261-269.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p261_Leit [ ]
---------- VANCOUVER ----------
Leit, S., Fernández Cirelli, A. Synthesis of anionic derivatives of methyl laminara-oligosaccharides and methyl β-maltoside. 1998;86(3-6):261-269.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p261_Leit [ ]