Conformations of ammonium 3-deoxy-D-manno-2-octulosonate (KDO) and methyl α- and β-ketopyranosides of KDO: X-ray structures and ¹H NMR analyses

Par Conseil national de recherches du Canada

Autre titre	Conformations of ammonium 3-deoxy-D-manno-2-octulosonate (KDO) and methyl α- and β-ketopyranosides of KDO: X-ray structure and 1H NMR analyses
DOI	Trouver le DOI : https://doi.org/10.1080/07328308708058858
Auteur	Rechercher : Birnbaum, George I.¹; Rechercher : Roy, René; Rechercher : Brisson, Jean-Robert¹; Rechercher : Jennings, Harold J.¹
Affiliation	Conseil national de recherches du Canada
Format	Texte, Article
Conférence	13th International Carbohydrate Symposium, Aug. 10-15, 1986, Ithaca, New York
Sujet	¹H; ¹H-NMR; alpha; conformation; conformations; H-¹ NMR; KDO; methyl; NMR; structure; X-ray; X-ray structure
Résumé	Ammonium 3-deoxy-D-manno-2-octulosonate monohydrate (KDO) crystallizes in the orthorhombic space group P2₁2₁2₁, and the cell dimensions are a - 6.9700(4)Å, b = 7.7230(4) Å, c = 23.4067 (12) Å. X-ray intensity data were measured on a diffractometer, and the structure was determined by direct methods. Least-squares refinement, which included all hydrogen atoms, converged at R = 0.034 for 1526 observed reflections. The pyranose ring exists in an almost perfect ⁵C₂ (D) chair conformation. The COO-, 4-OH and 6-CHOHCH₂OH groups are In equatorial orientation, while the 2-OH and 5-OH groups are axial. The solution conformations of the ammonium salts of methyl α- and β-ketopyranosides of KDO were determined by high-resolution ¹H NMR spectroscopy. The conformation of the ethylene glycol side chain in the α-methyl glycopyranoside of KDO was found to be indistinguishable from that in the solid state. However, the solution conformation of the side chain is different in the β-anomer, possibly indicative of an intramolecular hydrogen bond between the 8-OH and carboxylate groups.
Date de publication	1987-12-31
Maison d’édition	Taylor and Francis
Dans	Journal of Carbohydrate Chemistry 6 : 17–39.
Langue	anglais
Publications évaluées par des pairs	Oui
Identificateur	NRC-IBS-BIRNBAUM1987
Numéro NPARC	9379415
Exporter la notice	Exporter en format RIS
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Identificateur de l’enregistrement	9af5b6c9-487f-43d9-a43c-5668d8c77000
Enregistrement créé	2009-07-10
Enregistrement modifié	2020-03-17

Date de modification :: 2024-07-06