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N-(2-Carb-oxy-eth-yl)-2,5-dide-oxy-2,5-imino-d-mannonic acid [(3R,4R,5R)-1-(2-carb-oxy-eth-yl)-3,4-dihy-droxy-5-hy-droxy-methyl-l-proline].

ABSTRACT: 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 mol-ecule acting as a donor and acceptor for four hydrogen bonds.

SUBMITTER: Edgeley DS 

PROVIDER: S-EPMC3470222 | biostudies-literature | 2012 Oct

REPOSITORIES: biostudies-literature

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N-(2-Carb-oxy-eth-yl)-2,5-dide-oxy-2,5-imino-d-mannonic acid [(3R,4R,5R)-1-(2-carb-oxy-eth-yl)-3,4-dihy-droxy-5-hy-droxy-methyl-l-proline].

Edgeley David S DS   Martínez R Fernando RF   Jenkinson Sarah F SF   Nash Robert J RJ   Fleet George W J GW   Thompson Amber L AL  

Acta crystallographica. Section E, Structure reports online 20120905 Pt 10

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 mol-ecule acting as a donor and acceptor  ...[more]

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