Reaction of guanosine with glucose under oxidative conditions

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 15, 1998, Pages 2017-2022

  Seidel, Wolfgang ^a   Pischetsrieder, Monika ^a  

^a Lebensmittelchemie der Univ M   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCOSE; GUANOSINE DERIVATIVE; N2 CARBOXYMETHYLGUANOSINE; UNCLASSIFIED DRUG;

ARTICLE; CARCINOGENESIS; DNA ADDUCT; DNA MODIFICATION; HEAT TREATMENT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; REACTION ANALYSIS; REACTION TIME; STRUCTURE ANALYSIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUCOSE; GUANOSINE; OXIDATION-REDUCTION; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0032483132     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00343-6     Document Type: Article

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20. 20 Guanosine (220 mg) and D-glucose (220 mg) in 2 ml phosphate buffer (1M, pH 7.4) were incubated for 24 d at 37 °C in an open vessel in a shaking water bath. After the reaction the mixture was analyzed by HPLC.
21. 21 a) Analytical HPLC was performed with a Merck L-7100 gradient pump fitted with a 20 μl sample loop and a L-7450 diode array detector including Merck-Hitachi Model D-7000 Chromatography Data Station software. A column packed with LiChrosphere™ (RP-18, 280 × 4 mm i.d., 5 μm particle size) was used. The column was protected with a guard cartridge (25×4mm), packed with the same material as the column. Eluent: gradient elution starting with ammonium formate buffer (5 mM, pH 4.5), ending within 25 min with 50:50 buffer:methanol at a flow rate of 0.8 ml/min. The substances were detected with a diode array detector from 220nm-400nm.
22. b) Preparative HPLC was performed with a Merck L-6250 preparative pump fitted with a 2 ml sample loop and a Merck L-4000 UV-detector. A column packed with Supelcosil™ (LC-18-DB, 250 × 21.2 mm i.d., 5 μm particle size) was used. A mixture of 96:4 ammonium formate buffer (5mM, pH 7) : methanol was used as solvent at a flow rate of 12 ml/min Substances were detected at 275 nm.
23. 22 Guanosine (220 mg) and D-glucose (220 mg) were dissolved in 2 ml phosphate buffer (1M, pH 7.4) containing 10 mg DTPA to chelate metal ions, which can catalyse oxidation. The solution was flushed with nitrogen, incubated for 24 d in a clossed vessel in a shaking water bath and analyzed by HPLC.
24. 23 Guanosine (210 mg) and D-glucose (220 mg) were dissolved in phosphate buffer (1M, pH 7.4) and incubated for 24 d in an open vessel at 70 °C in a shaking water bath. The reaction mixture was directly injected into preparative HPLC.
25. max = 256 nm.
26. 25 Guanosine (200 mg) and glyoxal (0.5 ml of a 40 % solution in water) were heated in 2 ml phosphate buffer (1M, pH 7.4) in a clossed vessel for 16 h at 100 °C. The reaction mixture was directly used for preparative HPLC.
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29. 27 Guanosine (100 mg), glyoxal (0.25 ml of a 40 % solution in water) and propylamine (250 mg) were dissolved in 1 ml water and the pH was adjusted with phosphoric acid to 7.4. The mixture was incubated for 7 d at 37 °C and analyzed by HPLC.
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