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Varela, O.; Zunszain, P.A.; Cicero, D.O.; Baggio, R.F.; Vega, D.R.; Garland, M.T. "Conformation of 4-thio-L-lyxono-1,4-lactone in solution and in the crystalline state" (1996) Carbohydrate Research. 280(2):187-196
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Abstract:

The conformation in 2H2O of 4-thio-L-lyxono-1,4-lactone (1) was studied by nuclear magnetic resonance spectroscopy, by means of homonuclear (J(1(H),1(H))) and heteronuclear (J(1(H),13(C))) coupling constants. The couplings were directly measured by a two-dimensional heteronucleus-coupled ω1 hetero-half-filtered proton-proton correlation (HETLOC) experiment, which does not require 13C isotopic enrichment. In solution, the thiolactone ring of 1 adopts preferentially the E3 conformation, and its hydroxymethyl group populates mainly the gt rotamer. The X-ray diffraction data of a single crystal of 1 indicates that also in the solid state the thiolactone ring adopts an E2 conformation, with a puckering somewhat larger than that observed for aldono-1,4-lactones and furanose rings. The molecules are linked by hydrogen bonds, which form chains. Particularly, O-5 is fully engaged as donor and acceptor in hydrogen bonding and the rotameric conformation of the hydroxymethyl group of 1 is fixed in the tg form.

Registro:

Documento: Artículo
Título:Conformation of 4-thio-L-lyxono-1,4-lactone in solution and in the crystalline state
Autor:Varela, O.; Zunszain, P.A.; Cicero, D.O.; Baggio, R.F.; Vega, D.R.; Garland, M.T.
Filiación:Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Ciudad Universitaria, (1428) Buenos Aires, Argentina
Div. Física del Sólido, Departamento de Física, Comn. Natl. de Ener. Atómica, Buenos Aires, Argentina
Departamento de Física, Fac. de Cie. Fis. y Matemat., Universidad de Chile, Santiago de Chile, Chile
Ist. di Ric. di Biologia Molecolare, via Pontina Km 30,600, Rome, Italy
Palabras clave:2D NMR heteronucleus-coupled H-H correlation (HETLOC); 13C-1H coupling constants; aldopentono-1,4-thiolactone conformation; heteronuclear; 4 thio l lyxono 1,4 lactone; thiolactone; unclassified drug; article; crystallography; drug structure; nuclear magnetic resonance; priority journal
Año:1996
Volumen:280
Número:2
Página de inicio:187
Página de fin:196
DOI: http://dx.doi.org/10.1016/0008-6215(95)00325-8
Título revista:Carbohydrate Research
Título revista abreviado:CARBOHYDR. RES.
ISSN:00086215
CODEN:CRBRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v280_n2_p187_Varela

Referencias:

  • Altona, C., Sundaralingam, M., (1972) J. Am. Chem. Soc., 94, pp. 8205-8212
  • Altona, C., Geise, H.J., Romers, C., (1968) Tetrahedron, 24, pp. 13-32
  • Horton, D., Walaszek, Z., (1982) Carbohydr. Res., 105, pp. 95-109
  • Angelotti, T., Krisko, M., O'Connor, T., Serianni, A.S., (1987) J. Am. Chem. Soc., 109, pp. 4464-4472
  • Horton, D., Wałaszek, Z., (1982) Carbohydr. Res., 105, pp. 111-129
  • Kinoshita, Y., Ruble, J.R., Jeffrey, G.A., (1981) Carbohydr. Res., 92, pp. 1-7. , and references cited therein
  • Varela, O., Zunszain, P.A., (1993) J. Org. Chem., 58, pp. 7860-7864
  • Schwarcz, J.A., Perlin, A.S., (1972) Can. J. Chem., 50, pp. 3667-3676
  • Wasylishen, R., Schaefer, T., (1972) Can. J. Chem., 50, pp. 2710-2712
  • Wollborn, U., Leibfritz, D., (1992) J. Magn. Reson., 98, pp. 142-146
  • Kurz, M., Schmieder, P., Kessler, H., (1991) Angew. Chem., Int. Ed. Engl., 30, pp. 1329-1331
  • Haasnoot, C.A.G., De Leeuw, F.A.A.M., Altona, C., (1980) Tetrahedron, 36, pp. 2783-2792
  • Cyr, N., Hamer, G.K., Perlin, A.S., (1978) Can. J. Chem., 56, pp. 297-301
  • Wu, G.D., Serianni, A.S., Barker, R., (1983) J. Org. Chem., 48, pp. 1750-1757
  • Marshall, J.L., (1983) Carbon-carbon and Carbon-proton NMR Couplings, pp. 26-29. , Verlag Chemie International, Deerfield Beach, FL, USA
  • Hamer, G.K., Balza, F., Cyr, N., Perlin, A.S., (1978) Can. J. Chem., 56, pp. 3109-3116
  • Cremer, D., Pople, J.A., (1975) J. Am. Chem. Soc., 97, pp. 1354-1358
  • Wolfe, S., (1972) Acc. Chem. Res., 5, pp. 102-111
  • Flack, H.D., (1983) Acta Crystallagr., Sect. A, 39, pp. 876-881
  • Sheldrick, G.M., (1986) SHELXS86, , Program for the solution of crystal structures, University of Göttingen, Germany
  • Sheldrick, G.M., (1993) SHELXS93, , Structure refinement package, University of Göttingen, Germany
  • Sheldrick, G.M., (1991) SHELXTL-PC Version 4.2, , Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA
  • Jeffrey, G.A., Lewis, L., (1978) Carbohydr. Res., 60, pp. 179-182
  • Taylor, R., Kennard, O., (1983) Acta Crystallogr., Sect. B, 39, pp. 133-138
  • Garbow, J.R., Weitekamp, D.P., Pines, A., (1982) Chem. Phys. Lett., 93, pp. 504-511

Citas:

---------- APA ----------
Varela, O., Zunszain, P.A., Cicero, D.O., Baggio, R.F., Vega, D.R. & Garland, M.T. (1996) . Conformation of 4-thio-L-lyxono-1,4-lactone in solution and in the crystalline state. Carbohydrate Research, 280(2), 187-196.
http://dx.doi.org/10.1016/0008-6215(95)00325-8
---------- CHICAGO ----------
Varela, O., Zunszain, P.A., Cicero, D.O., Baggio, R.F., Vega, D.R., Garland, M.T. "Conformation of 4-thio-L-lyxono-1,4-lactone in solution and in the crystalline state" . Carbohydrate Research 280, no. 2 (1996) : 187-196.
http://dx.doi.org/10.1016/0008-6215(95)00325-8
---------- MLA ----------
Varela, O., Zunszain, P.A., Cicero, D.O., Baggio, R.F., Vega, D.R., Garland, M.T. "Conformation of 4-thio-L-lyxono-1,4-lactone in solution and in the crystalline state" . Carbohydrate Research, vol. 280, no. 2, 1996, pp. 187-196.
http://dx.doi.org/10.1016/0008-6215(95)00325-8
---------- VANCOUVER ----------
Varela, O., Zunszain, P.A., Cicero, D.O., Baggio, R.F., Vega, D.R., Garland, M.T. Conformation of 4-thio-L-lyxono-1,4-lactone in solution and in the crystalline state. CARBOHYDR. RES. 1996;280(2):187-196.
http://dx.doi.org/10.1016/0008-6215(95)00325-8