Conformation of 4-thio-L-lyxono-1,4-lactone in solution and in the crystalline state

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-h...

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Autores principales:	Varela, Oscar José, Zunszain, Patricia Ana, Cicero, Daniel Oscar, Baggio, Ricardo F., Vega, Daniel Roberto
Publicado:	1996
Materias:	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
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v280_n2_p187_Varela http://hdl.handle.net/20.500.12110/paper_00086215_v280_n2_p187_Varela
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00086215_v280_n2_p187_Varela
record_format	dspace
spelling	paper:paper_00086215_v280_n2_p187_Varela2023-06-08T14:32:34Z Conformation of 4-thio-L-lyxono-1,4-lactone in solution and in the crystalline state Varela, Oscar José Zunszain, Patricia Ana Cicero, Daniel Oscar Baggio, Ricardo F. Vega, Daniel Roberto 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 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. Fil:Varela, O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Zunszain, P.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Cicero, D.O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Baggio, R.F. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Vega, D.R. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 1996 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v280_n2_p187_Varela http://hdl.handle.net/20.500.12110/paper_00086215_v280_n2_p187_Varela
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	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
spellingShingle	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 Varela, Oscar José Zunszain, Patricia Ana Cicero, Daniel Oscar Baggio, Ricardo F. Vega, Daniel Roberto Conformation of 4-thio-L-lyxono-1,4-lactone in solution and in the crystalline state
topic_facet	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
description	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.
author	Varela, Oscar José Zunszain, Patricia Ana Cicero, Daniel Oscar Baggio, Ricardo F. Vega, Daniel Roberto
author_facet	Varela, Oscar José Zunszain, Patricia Ana Cicero, Daniel Oscar Baggio, Ricardo F. Vega, Daniel Roberto
author_sort	Varela, Oscar José
title	Conformation of 4-thio-L-lyxono-1,4-lactone in solution and in the crystalline state
title_short	Conformation of 4-thio-L-lyxono-1,4-lactone in solution and in the crystalline state
title_full	Conformation of 4-thio-L-lyxono-1,4-lactone in solution and in the crystalline state
title_fullStr	Conformation of 4-thio-L-lyxono-1,4-lactone in solution and in the crystalline state
title_full_unstemmed	Conformation of 4-thio-L-lyxono-1,4-lactone in solution and in the crystalline state
title_sort	conformation of 4-thio-l-lyxono-1,4-lactone in solution and in the crystalline state
publishDate	1996
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v280_n2_p187_Varela http://hdl.handle.net/20.500.12110/paper_00086215_v280_n2_p187_Varela
work_keys_str_mv	AT varelaoscarjose conformationof4thiollyxono14lactoneinsolutionandinthecrystallinestate AT zunszainpatriciaana conformationof4thiollyxono14lactoneinsolutionandinthecrystallinestate AT cicerodanieloscar conformationof4thiollyxono14lactoneinsolutionandinthecrystallinestate AT baggioricardof conformationof4thiollyxono14lactoneinsolutionandinthecrystallinestate AT vegadanielroberto conformationof4thiollyxono14lactoneinsolutionandinthecrystallinestate
_version_	1768544620875087872

Conformation of 4-thio-L-lyxono-1,4-lactone in solution and in the crystalline state

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