2D- and 3D- potential energy surfaces of β-(1→3)-linked disaccharides calculated with the MM3 force-field
The adiabatic conformational surfaces of sixteen 4′,6′,6-trideoxy-β-D-(1→3)-linked disaccharides were obtained using the MM3 force-field. Calculations were carried out on disaccharides with different configurations at C2, C4 and C2′, which are neighbors to the glycosidic linkage, as well as that of...
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2003
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| LEADER | 12555caa a22011057a 4500 | ||
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| 001 | PAPER-4910 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203430.0 | ||
| 008 | 190411s2003 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0037827684 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JCACD | ||
| 100 | 1 | |a Stortz, C.A. | |
| 245 | 1 | 0 | |a 2D- and 3D- potential energy surfaces of β-(1→3)-linked disaccharides calculated with the MM3 force-field |
| 260 | |c 2003 | ||
| 270 | 1 | 0 | |m Stortz, C.A.; Depto. de Quim. Organ.-CIHIDECAR, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina; email: stortz@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a French, A.D., Brady, J.W., Computer modeling of carbohydrates (1990) ACS Symp. Ser., 430, pp. 1-19 | ||
| 504 | |a Engelsen, S.B., Rasmussen, K., Conformations of disaccharides by empirical force field calculations. Part v: Conformational maps of β-gentiobiose in an optimized consistent force field (1993) Int. J. Biol. Macromol., 15 (1), pp. 56-62 | ||
| 504 | |a French, A.D., Dowd, M.K., Exploration of disaccharide conformations by molecular mechanics (1993) J. Mol. Struct., Theochem., 286, pp. 183-201 | ||
| 504 | |a Melberg, S., Rasmussen, K., Conformations of disaccharides by empirical force-field calculations. Part I, β-maltose (1979) Carbohydr. Res., 69, pp. 27-38 | ||
| 504 | |a Melberg, S., Rasmussen, K., Conformations of disaccharides by empirical force-field calculations. Part II, β-cellobiose (1979) Carbohydr. Res., 71, pp. 25-34 | ||
| 504 | |a Melberg, S., Rasmussen, K., Conformations of disaccharides by empirical, force-field calculations. Part III, β-gentiobiose (1980) Carbohydr. Res., 78, pp. 215-224 | ||
| 504 | |a Tvaroška, I., Pérez, S., Conformational energy calculations for oligosaccharides: A comparison of methods and a strategy of calculation (1986) Carbohydr. Res., 149 (2), pp. 389-410 | ||
| 504 | |a French, A.D., Rigid- and relaxed-residue conformational analyses of cellobiose using the computer program MM2 (1988) Biopolymers, 27 (9), pp. 1519-1525 | ||
| 504 | |a Ha, S.N., Madsen, L.J., Brady, J.W., Conformational analysis and molecular dynamics simulations of maltose (1988) Biopolymers, 27 (12), pp. 1927-1952 | ||
| 504 | |a French, A.D., Comparison of rigid and relaxed conformational maps for cellobiose and maltose (1989) Carbohydr. Res., 188, pp. 206-211 | ||
| 504 | |a Tran, V., Buléon, A., Imberty, A., Pérez, S., Relaxed potential energy surfaces of maltose (1989) Biopolymers, 28, pp. 679-690 | ||
| 504 | |a Imberty, A., Tran, V., Pérez, S., Relaxed potential energy surfaces of N-linked oligosaccharides: The mannose-α-(1 → 3)-mannose case (1989) J. Comput. Chem., 11 (2), pp. 205-216 | ||
| 504 | |a Allinger, N.L., Yuh, Y.H., Lii, J.-H., Molecular mechanics. The MM3 force field for hydrocarbons (1989) J. Am. Chem. Soc., 111 (23), pp. 8551-8566 | ||
| 504 | |a Allinger, N.L., Rahman, M., Lii, J.-H., A molecular mechanics force field (MM3) for alcohols and ethers (1990) J. Am. Chem. Soc., 112 (23), pp. 8293-8307 | ||
| 504 | |a Koca, J., Pérez, S., Imberty, A., Conformational analysis and flexibility of carbohydrates using the CICADA approach with MM3 (1995) J. Comput. Chem., 16 (3), pp. 296-310 | ||
| 504 | |a Koca, J., Potential energy hypersurface and molecular flexibility (1993) J. Mol. Struct., 291, pp. 255-269 | ||
| 504 | |a Dowd, M.K., Reilly, P.J., French, A.D., Conformational analysis of trehalose disaccharides and analogues using MM3 (1992) J. Comput. Chem., 13 (1), pp. 102-114 | ||
| 504 | |a Dowd, M.K., Zeng, J., French, A.D., Reilly, P.J., Conformational analysis of the anomeric forms of kojibiose, nigerose, and maltose using MM3 (1992) Carbohydr. Res., 230, pp. 223-244 | ||
| 504 | |a Dowd, M.K., French, A.D., Reilly, P.J., Molecular mechanics modeling of α-(1 → 2), α-(1 → 3), and α-(1 → 6)-linked mannosyl disaccharides with MM3(92) (1995) J. Carbohydr. Chem., 14 (4-5), pp. 589-600 | ||
| 504 | |a Dowd, M.K., French, A.D., Reilly, P.J., Conformational analysis of the anomeric forms of sophorose, laminaribiose, and cellobiose using MM3 (1992) Carbohydr. Res., 233, pp. 15-34 | ||
| 504 | |a Stortz, C.A., Disaccharide conformational maps: How adiabatic is an adiabatic map? (1999) Carbohydr. Res., 322, pp. 77-86 | ||
| 504 | |a French, A.D., Kelterer, A.-M., Johnson, G.P., Dowd, M.K., Cramer, C.J., HF/6-31G* Energy surfaces for disaccharide analogs (2001) J. Comput. Chem., 22 (1), pp. 65-78 | ||
| 504 | |a French, A.D., Kelterer, A.-M., Cramer, C.J., Johnson, G.P., Dowd, M.K., A QM/MM analysis of the conformations of crystalline sucrose moieties (2000) Carbohydr. Res., 326, pp. 305-322 | ||
| 504 | |a French, A.D., Kelterer, A.-M., Johnson, G.P., Dowd, M.K., Cramer, C.J., Constructing and evaluating energy surfaces of crystalline disaccharides (2000) J. Mol. Graph. Model., 18 (2), pp. 95-107 | ||
| 504 | |a Stortz, C.A., Cerezo, A.S., Disaccharide conformational maps: 3D contours or 2D plots? (2002) Carbohydr. Res., 337, pp. 1861-1871 | ||
| 504 | |a Rees, D.A., (1977) Polysaccharide Shapes, p. 51. , Chapman & Hall: London | ||
| 504 | |a Stortz, C.A., Cerezo, A.S., Conformational analysis of sulfated α-(1 → 3)-linked D-galactobioses using the MM3 force-field (1998) J. Carbohydr. Chem., 17 (9), pp. 1405-1419 | ||
| 504 | |a Stortz, C.A., Cerezo, A.S., Conformational analysis of neocarrabiose and its sulfated and/or pyruvylated derivatives using the MM3 force-field (2000) J. Carbohydr. Chem., 19 (9), pp. 1115-1130 | ||
| 504 | |a Stortz, C.A., Potential energy surfaces of carrageenan models: Carrabiose, β-(1 → 4)-linked D-galactobiose, and their sulfated derivatives (2002) Carbohydr. Res., 337 (21-23), pp. 2311-2323 | ||
| 504 | |a Stortz, C.A., Cerezo, A.S., Potential energy surfaces of α-(1 → 3)-linked disaccharides calculated with the MM3 force-field (2002) J. Carbohydr. Chem., 21 (5), pp. 355-371 | ||
| 504 | |a (1997) Bull. QCPE, 17 (1), p. 3 | ||
| 504 | |a Engelsen, S.B., Rasmussen, K., β-Lactose in the view of a CFF-optimized force field (1997) J. Carbohydr. Chem., 16 (6), pp. 773-788 | ||
| 504 | |a Takeda, H., Yasuoka, N., Kasai, N., The crystal and molecular structure of a 3:2 mixture of laminarabiose and O-α-D-glucopyranosyl-(1 → 3)-β-D-glucopyranose (1977) Carbohydr. Res., 53, pp. 137-152 | ||
| 504 | |a Takeda, H., Kaiya, T., Yasuoka, N., Kasai, N., The crystal and molecular structure of methyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)- β-D-glucopyranoside (methyl 2,3,4,6,2′,4′,6′-hepta-O-acetyl-β-D-laminarabioside) (1978) Carbohydr. Res., 62, pp. 27-37 | ||
| 504 | |a Perez, S., Vergelati, C., Tran, V.H., Real-space crystal structure solution. Crystal and molecular structure of laminarabiose octaacetate, C28H38O19 (1985) Acta Crystallogr., Sect. B, 41, pp. 262-275 | ||
| 504 | |a Noguchi, K., Okuyama, K., Kitamura, S., Takeo, K., Crystal structure of methyl 3-O-β-D-glucopyranosyl-β-D-glucopyranoside (methyl β-D-laminarabioside) mono-hydrate (1992) Carbohydr. Res., 237, pp. 33-43 | ||
| 504 | |a Ikegami, M., Noguchi, K., Okuyama, K., Kitamura, S., Takeo, K., Ohno, S., Molecular and crystal structure of methyl hepta-O-acetyl-α-laminarabioside (1994) Carbohydr. Res., 253, pp. 29-38 | ||
| 504 | |a Noguchi, K., Kobayashi, E., Okuyama, K., Kitamura, S., Takeo, K., Ohno, S., Molecular and crystal structure of (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1 → 3)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1 → 6)-(2,4-di-O-acetyl-β-D-glucopyranosyl)-(1 → 3)-1,2,4,6-tetra-O-acetyl-β-D-glucopyranose (1994) Carbohydr. Res., 258, pp. 35-47 | ||
| 504 | |a Foces-Foces, C., Cano, F.H., García-Blanco, S., 1,2,4,6-Tetra-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D- galactopyranosyl)-α-D-galactopyranose (1980) Acta Crystallogr., Sect. B, 36, pp. 377-384 | ||
| 504 | |a Mendonca, S., Johnson, G.P., French, A.D., Laine, R.A., Conformational analyses of native and permethylated disaccharides (2002) J. Chem. Phys. A, 106, pp. 4115-4124 | ||
| 504 | |a Rees, D.A., Scott, W.E., Polysaccharide conformation. Part VI. Computer model-building for linear and branched pyranoglycans. Correlations with biological function. Preliminary assessment of inter-residue forces in aqueous solution. Further interpretation of optical rotation in terms of chain conformation (1971) J. Chem. Soc., B, pp. 469-479 | ||
| 504 | |a Kochetkov, N.K., Chizhov, O.S., Shashkov, A.S., Dependence of 13C chemical shifts on the spatial interaction of protons, and its application in structural and conformational studies of oligo- and polysaccharides (1984) Carbohydr. Res., 133, pp. 173-185 | ||
| 504 | |a Shashkov, A.S., Lipkind, G.M., Knirel, Yu.A., Kochetkov, N.K., Stereochemical factors determining the effects of glycosylation on the 13C chemical shifts in carbohydrates (1988) Magn. Reson. Chem., 26, pp. 735-747 | ||
| 504 | |a Bock, K., Brignole, A., Sigurskjold, B.W., Conformational dependence of 13C nuclear magnetic resonance chemical shifts in oligosaccharides (1986) J. Chem. Soc., Perkin Trans. 2, pp. 1711-1713 | ||
| 520 | 3 | |a The adiabatic conformational surfaces of sixteen 4′,6′,6-trideoxy-β-D-(1→3)-linked disaccharides were obtained using the MM3 force-field. Calculations were carried out on disaccharides with different configurations at C2, C4 and C2′, which are neighbors to the glycosidic linkage, as well as that of the linked carbon (C3). The surfaces were plotted as contour maps and as 2D graphs representing the energy vs. the ψ angle. The resulting maps were similar in each case, indicating that the substituents do not play a major role in the conformational features of these disaccharides. However, the number of minima, the preferred minimum conformation and the flexibility depended on the configurations of the mentioned carbons. Vicinal equatorial substituents tend to decrease the overall flexibility, especially those on C2, although cross over effects were found. The relative stabilities of the minimal energy conformations of the 16 compounds were compared with those of their equivalent α-linked counterparts. Deviations of the predicted increased stabilities of equatorially substituted compounds over axially substituted ones follow a relationship with their configurations, and consequently can serve to formulate predictive trends. |l eng | |
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires, X087 | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: Both authors are Research Members of the Argentine Research Council (CONICET). This work was supported by grants from UBA (X087), CONICET and Vitae-Antorchas. | ||
| 593 | |a Depto. de Quim. Organ.-CIHIDECAR, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina | ||
| 593 | |a Depto. de Quim. Organ.-CIHIDECAR, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a AXIAL |
| 690 | 1 | 0 | |a CONFORMATIONAL ANALYSIS |
| 690 | 1 | 0 | |a DISACCHARIDE MAPS |
| 690 | 1 | 0 | |a EQUATORIAL |
| 690 | 1 | 0 | |a MM3 |
| 690 | 1 | 0 | |a DISACCHARIDE |
| 690 | 1 | 0 | |a FUNCTIONAL GROUP |
| 690 | 1 | 0 | |a ANALYTIC METHOD |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CALCULATION |
| 690 | 1 | 0 | |a COMPUTER PROGRAM |
| 690 | 1 | 0 | |a CONFORMATIONAL TRANSITION |
| 690 | 1 | 0 | |a CORRELATION ANALYSIS |
| 690 | 1 | 0 | |a ENERGY RESOURCE |
| 690 | 1 | 0 | |a ENTROPY |
| 690 | 1 | 0 | |a LINKAGE ANALYSIS |
| 690 | 1 | 0 | |a MOLECULAR MECHANICS |
| 690 | 1 | 0 | |a STRUCTURE ANALYSIS |
| 690 | 1 | 0 | |a SUBSTITUTION REACTION |
| 700 | 1 | |a Cerezo, A.S. | |
| 773 | 0 | |d 2003 |g v. 22 |h pp. 217-239 |k n. 3-4 |p J. Carbohydr. Chem. |x 07328303 |w (AR-BaUEN)CENRE-573 |t Journal of Carbohydrate Chemistry | |
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