Structural Analysis of Total Anionic Cyclosophoraoses Synthesized by Rhizobium meliloti 2011

Seo, Dong-Huyk; Lee, Sang-Hoo; Park, Hay-Lin; Lee, Dong-Heui; Ji, Eun-Jung; Shin, Dae-Ho; Jung, Seunho

doi:10.5012/bkcs.2002.23.6.899

Bulletin of the Korean Chemical Society

2002

DOI: 10.5012/bkcs.2002.23.6.899

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Structural Analysis of Total Anionic Cyclosophoraoses Synthesized by Rhizobium meliloti 2011

Dong-Huyk Seo¹,

Sang-Hoo Lee²,

Hay-Lin Park³

et al.

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Cited by 8 publications

References 12 publications

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Chiral recognition based on enantioselective interactions of propranolol enantiomers with cyclosophoraoses isolated from Rhizobium meliloti

Lee¹,

Choi²,

Lee³

et al. 2004

Chirality

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Cyclosophoraoses isolated from Rhizobium meliloti, as an NMR chiral shift agent, were used to discriminate propranolol enantiomers. Continuous variation plot made from the complex of cyclosophoraoses with propranolol showed that the diastereomeric complex had predominantly 1:1 stoichiometry through UV spectroscopic analysis. The chiral recognition of propranolol enantiomers by cyclosophoraoses was investigated through the determination of binding constant based on the (13)C NMR chemical shift changes. The averaged K(obs) values from the plots were 55.7 M(-1) for (R)-(+)-propranolol and 36.6 M(-1) for (S)-(-)-propranolol, respectively. Enantioselectivity (alpha = K(R+)/K(S(-)) of 1.52 was then obtained. Computational calculation also revealed that (R)-(+) propranolol was more tightly bound with cyclosophoraose than (S)-(-)-propranolol due to the enhanced van der Waals interaction.

show abstract

Chiral recognition based on enantioselective interactions of propranolol enantiomers with cyclosophoraoses isolated from Rhizobium meliloti

Lee¹,

Choi²,

Lee³

et al. 2004

Chirality

View full text Add to dashboard Cite

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Enantioseparation using sulfated cyclosophoraoses as a novel chiral additive in capillary electrophoresis

Park

Lee²,

Kang

et al. 2004

Electrophoresis

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Highly sulfated cyclosophoraoses (HS-Cys) were synthesized by the chemical modification of a family of neutral cyclosophoraoses isolated from Rhizobium leguminosarum bv. trifolii. The HS-Cys were then analytically characterized using Fourier transform-infrared spectroscopy and elemental analysis. These HS-Cys were successfully used as a novel chiral additive, in low-pH aqueous background electrolytes, for capillary electrophoretic separation of five basic chiral drugs such as arterenol, atenolol, isoproterenol, propranolol, and metoprolol.

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Synthesis and characterization of carboxymethylated cyclosophoraose, and its inclusion complexation behavior

Lee¹,

Park²,

Seo³

et al. 2004

Carbohydrate Research

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Structural Analysis of Total Anionic Cyclosophoraoses Synthesized by Rhizobium meliloti 2011

Cited by 8 publications

References 12 publications

Chiral recognition based on enantioselective interactions of propranolol enantiomers with cyclosophoraoses isolated from Rhizobium meliloti

Chiral recognition based on enantioselective interactions of propranolol enantiomers with cyclosophoraoses isolated from Rhizobium meliloti

Enantioseparation using sulfated cyclosophoraoses as a novel chiral additive in capillary electrophoresis

Synthesis and characterization of carboxymethylated cyclosophoraose, and its inclusion complexation behavior

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