N-(2-Carb­oxy­eth­yl)-2,5-dide­oxy-2,5-imino-d-mannonic acid [(3R,4R,5R)-1-(2-carb­oxy­eth­yl)-3,4-dihy­droxy-5-hy­droxy­methyl-l-proline]

The absolute stereochemistry of the title compound, C(9)H(15)NO(7), was determined from the use of d-glucuronolactone as the starting material. The compound crystallizes as the zwitterion. The five-membered ring adopts an envelope conformation with the –CH(2)OH-substituted C atom forming the flap. A...

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Detalles Bibliográficos
Autores principales: Edgeley, David S., Martínez, R. Fernando, Jenkinson, Sarah F., Nash, Robert J., Fleet, George W. J., Thompson, Amber L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3470222/
https://www.ncbi.nlm.nih.gov/pubmed/23125666
http://dx.doi.org/10.1107/S1600536812037488
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author Edgeley, David S.
Martínez, R. Fernando
Jenkinson, Sarah F.
Nash, Robert J.
Fleet, George W. J.
Thompson, Amber L.
author_facet Edgeley, David S.
Martínez, R. Fernando
Jenkinson, Sarah F.
Nash, Robert J.
Fleet, George W. J.
Thompson, Amber L.
author_sort Edgeley, David S.
collection PubMed
description The absolute stereochemistry of the title compound, C(9)H(15)NO(7), was determined from the use of d-glucuronolactone as the starting material. The compound crystallizes as the zwitterion. The five-membered ring adopts an envelope conformation with the –CH(2)OH-substituted C atom forming the flap. An intramolecular N—H⋯O hydrogen-bond occurs. In the crystal, the compound exists as a three-dimensional O—H⋯O intermolecular hydrogen-bonded network with each mol­ecule acting as a donor and acceptor for four hydrogen bonds.
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spelling pubmed-34702222012-11-02 N-(2-Carb­oxy­eth­yl)-2,5-dide­oxy-2,5-imino-d-mannonic acid [(3R,4R,5R)-1-(2-carb­oxy­eth­yl)-3,4-dihy­droxy-5-hy­droxy­methyl-l-proline] Edgeley, David S. Martínez, R. Fernando Jenkinson, Sarah F. Nash, Robert J. Fleet, George W. J. Thompson, Amber L. Acta Crystallogr Sect E Struct Rep Online Organic Papers The absolute stereochemistry of the title compound, C(9)H(15)NO(7), was determined from the use of d-glucuronolactone as the starting material. The compound crystallizes as the zwitterion. The five-membered ring adopts an envelope conformation with the –CH(2)OH-substituted C atom forming the flap. An intramolecular N—H⋯O hydrogen-bond occurs. In the crystal, the compound exists as a three-dimensional O—H⋯O intermolecular hydrogen-bonded network with each mol­ecule acting as a donor and acceptor for four hydrogen bonds. International Union of Crystallography 2012-09-05 /pmc/articles/PMC3470222/ /pubmed/23125666 http://dx.doi.org/10.1107/S1600536812037488 Text en © Edgeley et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Edgeley, David S.
Martínez, R. Fernando
Jenkinson, Sarah F.
Nash, Robert J.
Fleet, George W. J.
Thompson, Amber L.
N-(2-Carb­oxy­eth­yl)-2,5-dide­oxy-2,5-imino-d-mannonic acid [(3R,4R,5R)-1-(2-carb­oxy­eth­yl)-3,4-dihy­droxy-5-hy­droxy­methyl-l-proline]
title N-(2-Carb­oxy­eth­yl)-2,5-dide­oxy-2,5-imino-d-mannonic acid [(3R,4R,5R)-1-(2-carb­oxy­eth­yl)-3,4-dihy­droxy-5-hy­droxy­methyl-l-proline]
title_full N-(2-Carb­oxy­eth­yl)-2,5-dide­oxy-2,5-imino-d-mannonic acid [(3R,4R,5R)-1-(2-carb­oxy­eth­yl)-3,4-dihy­droxy-5-hy­droxy­methyl-l-proline]
title_fullStr N-(2-Carb­oxy­eth­yl)-2,5-dide­oxy-2,5-imino-d-mannonic acid [(3R,4R,5R)-1-(2-carb­oxy­eth­yl)-3,4-dihy­droxy-5-hy­droxy­methyl-l-proline]
title_full_unstemmed N-(2-Carb­oxy­eth­yl)-2,5-dide­oxy-2,5-imino-d-mannonic acid [(3R,4R,5R)-1-(2-carb­oxy­eth­yl)-3,4-dihy­droxy-5-hy­droxy­methyl-l-proline]
title_short N-(2-Carb­oxy­eth­yl)-2,5-dide­oxy-2,5-imino-d-mannonic acid [(3R,4R,5R)-1-(2-carb­oxy­eth­yl)-3,4-dihy­droxy-5-hy­droxy­methyl-l-proline]
title_sort n-(2-carb­oxy­eth­yl)-2,5-dide­oxy-2,5-imino-d-mannonic acid [(3r,4r,5r)-1-(2-carb­oxy­eth­yl)-3,4-dihy­droxy-5-hy­droxy­methyl-l-proline]
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3470222/
https://www.ncbi.nlm.nih.gov/pubmed/23125666
http://dx.doi.org/10.1107/S1600536812037488
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