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
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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
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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
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Volumen: | 280
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Número: | 2
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Página de inicio: | 187
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Página de fin: | 196
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DOI: |
http://dx.doi.org/10.1016/0008-6215(95)00325-8 |
Título revista: | Carbohydrate Research
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Título revista abreviado: | CARBOHYDR. RES.
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ISSN: | 00086215
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CODEN: | CRBRA
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v280_n2_p187_Varela |
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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