Determination of association constants between 5'-guanosine monophosphate gel and aromatic compounds by capillary electrophoresis

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Abstract

Hydro gel formed by 5'-guanosine monophosphate (GMP) in the presence of a potassium ion is expected to exhibit interesting selectivity in capillary electrophoretic separations. Here, we estimated the conditional association constants between the hydro gel (G-gel) and aromatic compounds by capillary electrophoresis in order to investigate the separation selectivity that is induced by the G-gel. Several aromatic compounds were separated in a solution containing GMP and potassium ion at different concentrations. The association constants were calculated by correlating the electrophoretic mobilities of the analytes obtained experimentally using a concentration of G-gel. During semi-quantitative estimation, naphthalene derivatives had larger association constants (Kass=10.3-16.8) compared with those of benzene derivatives (Kass=3.91-5.31), which means that the binding sites of G-gel match better to a naphthalene ring than to a benzene ring. A hydrophobic interaction was also found when the association constants for alkyl resorcinol were compared with those of different hydrocarbon chains. The association constants of nucleobases and tryptophan ranged from 6.05 to 12.6, which approximated the intermediate values between benzene and naphthalene derivatives. Consequently, the selective interaction between G-gel and aromatic compounds was classified as one of three types: (1) an intercalation into stacked planar GMP tetramers; (2) a hydrophobic interaction with a long alkyl chain; or, (3) a small contribution of steric hindrance and/or hydrogen bonding with functional groups such as amino and hydroxyl groups.

Original languageEnglish
Pages (from-to)149-154
Number of pages6
JournalJournal of Chromatography A
Volume1288
DOIs
Publication statusPublished - May 3 2013

Fingerprint

Guanosine Monophosphate
Capillary electrophoresis
Aromatic compounds
Capillary Electrophoresis
Gels
Association reactions
Benzene Derivatives
Benzene
Hydrophobic and Hydrophilic Interactions
Potassium
Ions
Derivatives
Electrophoretic mobility
Hydrogen Bonding
Intercalation
Hydrocarbons
Tryptophan
Hydroxyl Radical
Functional groups
Hydrogen bonds

Keywords

  • 5'-Guanosine monophosphate (GMP)
  • Association constant
  • Capillary electrophoresis
  • G-gel

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

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title = "Determination of association constants between 5'-guanosine monophosphate gel and aromatic compounds by capillary electrophoresis",
abstract = "Hydro gel formed by 5'-guanosine monophosphate (GMP) in the presence of a potassium ion is expected to exhibit interesting selectivity in capillary electrophoretic separations. Here, we estimated the conditional association constants between the hydro gel (G-gel) and aromatic compounds by capillary electrophoresis in order to investigate the separation selectivity that is induced by the G-gel. Several aromatic compounds were separated in a solution containing GMP and potassium ion at different concentrations. The association constants were calculated by correlating the electrophoretic mobilities of the analytes obtained experimentally using a concentration of G-gel. During semi-quantitative estimation, naphthalene derivatives had larger association constants (Kass=10.3-16.8) compared with those of benzene derivatives (Kass=3.91-5.31), which means that the binding sites of G-gel match better to a naphthalene ring than to a benzene ring. A hydrophobic interaction was also found when the association constants for alkyl resorcinol were compared with those of different hydrocarbon chains. The association constants of nucleobases and tryptophan ranged from 6.05 to 12.6, which approximated the intermediate values between benzene and naphthalene derivatives. Consequently, the selective interaction between G-gel and aromatic compounds was classified as one of three types: (1) an intercalation into stacked planar GMP tetramers; (2) a hydrophobic interaction with a long alkyl chain; or, (3) a small contribution of steric hindrance and/or hydrogen bonding with functional groups such as amino and hydroxyl groups.",
keywords = "5'-Guanosine monophosphate (GMP), Association constant, Capillary electrophoresis, G-gel",
author = "Kaori Yamaguchi and Nobuyuki Takeyasu and Takashi Kaneta",
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language = "English",
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journal = "Journal of Chromatography",
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T1 - Determination of association constants between 5'-guanosine monophosphate gel and aromatic compounds by capillary electrophoresis

AU - Yamaguchi, Kaori

AU - Takeyasu, Nobuyuki

AU - Kaneta, Takashi

PY - 2013/5/3

Y1 - 2013/5/3

N2 - Hydro gel formed by 5'-guanosine monophosphate (GMP) in the presence of a potassium ion is expected to exhibit interesting selectivity in capillary electrophoretic separations. Here, we estimated the conditional association constants between the hydro gel (G-gel) and aromatic compounds by capillary electrophoresis in order to investigate the separation selectivity that is induced by the G-gel. Several aromatic compounds were separated in a solution containing GMP and potassium ion at different concentrations. The association constants were calculated by correlating the electrophoretic mobilities of the analytes obtained experimentally using a concentration of G-gel. During semi-quantitative estimation, naphthalene derivatives had larger association constants (Kass=10.3-16.8) compared with those of benzene derivatives (Kass=3.91-5.31), which means that the binding sites of G-gel match better to a naphthalene ring than to a benzene ring. A hydrophobic interaction was also found when the association constants for alkyl resorcinol were compared with those of different hydrocarbon chains. The association constants of nucleobases and tryptophan ranged from 6.05 to 12.6, which approximated the intermediate values between benzene and naphthalene derivatives. Consequently, the selective interaction between G-gel and aromatic compounds was classified as one of three types: (1) an intercalation into stacked planar GMP tetramers; (2) a hydrophobic interaction with a long alkyl chain; or, (3) a small contribution of steric hindrance and/or hydrogen bonding with functional groups such as amino and hydroxyl groups.

AB - Hydro gel formed by 5'-guanosine monophosphate (GMP) in the presence of a potassium ion is expected to exhibit interesting selectivity in capillary electrophoretic separations. Here, we estimated the conditional association constants between the hydro gel (G-gel) and aromatic compounds by capillary electrophoresis in order to investigate the separation selectivity that is induced by the G-gel. Several aromatic compounds were separated in a solution containing GMP and potassium ion at different concentrations. The association constants were calculated by correlating the electrophoretic mobilities of the analytes obtained experimentally using a concentration of G-gel. During semi-quantitative estimation, naphthalene derivatives had larger association constants (Kass=10.3-16.8) compared with those of benzene derivatives (Kass=3.91-5.31), which means that the binding sites of G-gel match better to a naphthalene ring than to a benzene ring. A hydrophobic interaction was also found when the association constants for alkyl resorcinol were compared with those of different hydrocarbon chains. The association constants of nucleobases and tryptophan ranged from 6.05 to 12.6, which approximated the intermediate values between benzene and naphthalene derivatives. Consequently, the selective interaction between G-gel and aromatic compounds was classified as one of three types: (1) an intercalation into stacked planar GMP tetramers; (2) a hydrophobic interaction with a long alkyl chain; or, (3) a small contribution of steric hindrance and/or hydrogen bonding with functional groups such as amino and hydroxyl groups.

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