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:

The adiabatic potential energy surfaces (PES) of two trisaccharides (β-cellotriose and α-maltotriose) were obtained using the MM3 force field. Each PES can be described by a single 3D contour map for which the energy is plotted against the two ψ glycosidic angles. Given the usually small variations of the φ glycosidic torsional angle in the low-energy regions of disaccharide maps (at least with MM3), it is valid to leave both φ glycosidic angles to relax in the process of building the conformational map of trisaccharides. The surfaces are those expected from the map of disaccharides containing the same linkages and monosaccharide units (i.e., β-cellobiose and α-maltose), with second-order factors altering the 'symmetry' of both linkages. A large low-energy region appears for β-cellotriose, comprising four minima in close proximity, with barriers between them below 0.6 kcal/mol. On the other hand, for α-maltotriose a main global minimum is observed, with several surrounding local minima. The surfaces obtained agree with single-crystal X-ray data on these trisaccharides and derivatives. A reduction of the linkage flexibilities is observed when passing from the disaccharides to the trisaccharides. Furthermore, the linkage closer to the reducing end appears to be less flexible than the linkage closer to the non-reducing end. © 2002 Elsevier Science Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Depicting the MM3 potential energy surfaces of trisaccharides by single contour maps: Application to β-cellotriose and α-maltotriose
Autor:Stortz, C.A.; Cerezo, A.S.
Filiación:Depto. Quim. Organica-CIHIDECAR, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:Conformational analysis; MM3; Molecular mechanics; Potential energy surfaces; Ramachandran map; Trisaccharides; Contour measurement; Potential energy; Single crystals; Surfaces; X ray analysis; Glycosidic angles; Carbohydrates; carbohydrate derivative; cellotriose; disaccharide; glycoside; maltotriose; monosaccharide; trisaccharide; unclassified drug; article; conformation; energy; molecular dynamics; priority journal; X ray crystallography; Carbohydrate Conformation; Cellulose; Models, Molecular; Thermodynamics; Trisaccharides
Año:2003
Volumen:338
Número:1
Página de inicio:95
Página de fin:107
DOI: http://dx.doi.org/10.1016/S0008-6215(02)00360-9
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:maltotriose, 1109-28-0; Cellulose, 9004-34-6; maltotriose, 1109-28-0; Trisaccharides
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v338_n1_p95_Stortz

Referencias:

  • French, A.D., Brady, J.W., (1990) ACS Symp. Ser., 430, pp. 1-19
  • Engelsen, S.B., Rasmussen, K., (1993) Int. J. Biol. Macromol., 15, pp. 56-62
  • French, A.D., Dowd, M.K., (1993) J. Mol. Struct. (Theochem.), 286, pp. 183-201
  • Melberg, S., Rasmussen, K., (1979) Carbohydr. Res., 69, pp. 27-38
  • Melberg, S., Rasmussen, K., (1979) Carbohydr. Res., 71, pp. 25-34
  • Tvaroška, I., Pérez, S., (1986) Carbohydr. Res., 149, pp. 389-410
  • French, A.D., (1988) Biopolymers, 27, pp. 1519-1523
  • Ha, S.N., Madsen, L.J., Brady, J.W., (1988) Biopolymers, 27, pp. 1927-1952
  • Tran, V., Buléon, A., Imberty, A., Pérez, S., (1989) Biopolymers, 28, pp. 679-690
  • French, A.D., (1989) Carbohydr. Res., 188, pp. 206-211
  • Dowd, M.K., Zeng, J., French, A.D., Reilly, P.J., (1992) Carbohydr. Res., 230, pp. 223-244
  • Dowd, M.K., French, A.D., Reilly, P.J., (1992) Carbohydr. Res., 233, pp. 15-34
  • Mendonca, S., Johnson, G.P., French, A.D., Laine, R.A., (2002) J. Phys. Chem., Sect. A, 106, pp. 4115-4124
  • Rees, D.A., (1970) J. Chem. Soc., Sect. B, pp. 877-884
  • Lipkind, G.M., Verovsky, V.E., Kochetkov, N.K., (1984) Carbohydr. Res., 133, pp. 1-13
  • Lipkind, G.M., Shashkov, A.S., Kochetkov, N.K., (1985) Carbohydr. Res., 141, pp. 191-197
  • Shashkov, A.S., Lipkind, G.M., Kochetkov, N.K., (1986) Carbohydr. Res., 147, pp. 175-182
  • Stevens, E.S., Sathyanarayana, B.K., (1989) J. Am. Chem. Soc., 111, pp. 4149-4154
  • Stevens, E.S., (1992) Biopolymers, 32, pp. 1571-1579
  • Momany, F.A., Willett, J.L., (2000) J. Comput. Chem., 21, pp. 1204-1219
  • Momany, F.A., Willett, J.L., (2000) Carbohydr. Res., 326, pp. 194-209
  • Homans, S.W., (1990) Biochemistry, 29, pp. 9110-9118
  • Homans, S.W., Forster, M., (1992) Glycobiology, 2, pp. 143-151
  • French, A.D., Mouhous-Riou, N., Pérez, S., (1993) Carbohydr. Res., 247, pp. 51-62
  • Koča, J., Pérez, S., Imberty, A., (1995) J. Comput. Chem., 16, pp. 296-310
  • Mazeau, K., Pérez, S., (1998) Carbohydr. Res., 311, pp. 203-217
  • Stortz, C.A., Cerezo, A.S., (2002) Carbohydr. Res., 337, pp. 1861-1871
  • Allinger, N.L., Yuh, Y.H., Lii, J.-H., (1989) J. Am. Chem. Soc., 111, pp. 8551-8566
  • Allinger, N.L., Rahman, M., Lii, J.-H., (1990) J. Am. Chem. Soc., 112, pp. 8293-8307
  • (1997) Bull. QCPE, 17 (1), p. 3
  • Engelsen, S.B., Koča, J., Braccini, I., Hervé du Penhoat, C., Pérez, S., (1995) Carbohydr. Res., 276, pp. 1-29
  • Engelsen, S.B., Rasmussen, K., (1997) J. Carbohydr. Chem., 16, pp. 773-788
  • Allen, F.H., Kennard, O., (1993) Chem. Des. Autom. News, 8, pp. 31-37
  • Bruno, I.J., Cole, J.C., Lommerse, J.P.M., Rowland, R.S., Taylor, R., Verdonk, M.L., (1997) J. Comput.-Aided Mol. Des., 11, pp. 525-537
  • Stortz, C.A., (1999) Carbohydr. Res., 322, pp. 77-86
  • Stortz, C.A., (2002) Carbohydr. Res., 337, pp. 2311-2323
  • Koča, J., (1993) J. Mol. Struct., 291, pp. 255-269
  • French, A.D., Kelterer, A.-M., Johnson, G.P., Dowd, M.K., Cramer, C.J., (2001) J. Comput. Chem., 22, pp. 65-78
  • Raymond, S., Henrisat, B., Qui, D.T., Kvick, Å., Chanzy, H., (1995) Carbohydr. Res., 277, pp. 209-229
  • Pérez, S., Brisse, F., (1977) Acta Crystallogr., Sect. B, 33, pp. 2578-2584
  • Pangborn, W., Langs, D., Pérez, S., (1985) Int. J. Biol. Macromol., 7, pp. 363-369
  • Gessler, K., Krauss, N., Steiner, T., Betzel, C., Sarko, A., Saenger, W., (1995) J. Am. Chem. Soc., 117, pp. 11397-11406
  • Hinrichs, H., Saenger, W., (1990) J. Am. Chem. Soc., 112, pp. 2789-2796
  • Brown, C.J., (1966) J. Chem. Soc., Sect. A, pp. 927-932
  • Chu, S.S.C., Jeffrey, G.A., (1968) Acta Crystallogr., Sect. B, 24, pp. 830-838
  • Ham, J.T., Williams, D.G., (1970) Acta Crystallogr., Sect. B, 26, pp. 1373-1383
  • Peralta-Inga, Z., Johnson, G.P., Dowd, M.K., French, A.D., Rendleman, J.A., Stevens, E.D., French, A.D., (2002) Carbohydr. Res., 337, pp. 851-861
  • Leeflang, B.R., Vliegenthart, J.F.G., Kroon-Batenburg, L.M.J., Van Eijck, B.P., Kroon, J., (1992) Carbohydr. Res., 230, pp. 41-61
  • Stortz, C.A., Cerezo, A.S., (2000) J. Carbohydr. Chem., 19, pp. 1115-1130
  • Stortz, C.A., Cerezo, A.S., (2002) J. Carbohydr. Chem., 21, pp. 355-371
  • Tvaroška, I., (1982) Biopolymers, 21, pp. 1887-1897
  • Quigley, G.J., Sarko, A., Marchessault, R.H., (1970) J. Am. Chem. Soc., 92, pp. 5834-5839
  • Poppe, L., Dabrowski, J., Von der Lieth, C.-W., Koike, K., Ogawa, T., (1990) Eur. J. Biochem., 189, pp. 313-325
  • Li, J., Ksebati, M.B., Zhang, W., Guo, Z., Wang, J., Yu, L., Fang, J., Wang, P.G., (1999) Carbohydr. Res., 315, pp. 76-88
  • Langan, P., Nishiyama, Y., Chanzy, H., (1999) J. Am. Chem. Soc., 121, pp. 9940-9946
  • Nishiyama, Y., Langan, P., Chanzy, H., (2002) J. Am. Chem. Soc., 124, pp. 9074-9082

Citas:

---------- APA ----------
Stortz, C.A. & Cerezo, A.S. (2003) . Depicting the MM3 potential energy surfaces of trisaccharides by single contour maps: Application to β-cellotriose and α-maltotriose. Carbohydrate Research, 338(1), 95-107.
http://dx.doi.org/10.1016/S0008-6215(02)00360-9
---------- CHICAGO ----------
Stortz, C.A., Cerezo, A.S. "Depicting the MM3 potential energy surfaces of trisaccharides by single contour maps: Application to β-cellotriose and α-maltotriose" . Carbohydrate Research 338, no. 1 (2003) : 95-107.
http://dx.doi.org/10.1016/S0008-6215(02)00360-9
---------- MLA ----------
Stortz, C.A., Cerezo, A.S. "Depicting the MM3 potential energy surfaces of trisaccharides by single contour maps: Application to β-cellotriose and α-maltotriose" . Carbohydrate Research, vol. 338, no. 1, 2003, pp. 95-107.
http://dx.doi.org/10.1016/S0008-6215(02)00360-9
---------- VANCOUVER ----------
Stortz, C.A., Cerezo, A.S. Depicting the MM3 potential energy surfaces of trisaccharides by single contour maps: Application to β-cellotriose and α-maltotriose. Carbohydr. Res. 2003;338(1):95-107.
http://dx.doi.org/10.1016/S0008-6215(02)00360-9