Analogs of Nucleotides. I. Theophyllinylalkylphosphonic Acids and Related Compounds<sup>1</sup>

Parikh, Jekishan R.; Burger, Alfred

doi:10.1021/ja01614a008

Cited by 8 publications

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“…The mobile phase, consisting of 100 ll diethylamine in n-hexane/2-propanol (92:8 v/v), was vacuum-degassed before use and pumped at a flow rate of 0.5 ml min 21 . Under these conditions, the approximate retention times were as follows: 1,3-dimethyl-7-(2 0chloroethyl)-1H-purine-2,6(3H,7H)-dione (internal standard) 24 : 11.80 min; 1,3-dibutyl-7-(2-oxopropyl)-1H-purine-2,6(3H,7H)-dione (DBF): 35.98 min; 1,3-dibutyl-7-((2 0 R)hydroxypropyl)-1H-purine-2,6(3H,7H)-dione: 25.45 min; 1, 3-dibutyl-7-((2 0 S)-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione: 28.87 min. No interference was observed at the retention times of interest.…”

Section: Methodsmentioning

confidence: 99%

Preparation of enantiopure (R)‐hydroxy metabolite of denbufylline using immobilized Lactobacillus kefiri DSM 20587 as a catalyst

2008

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Lactobacillus kefiri DSM 20587 cells were immobilized in calcium alginate and carrageenan. The immobilized cells were used as biocatalysts for the enantioselective reduction of the methyl ketone group of denbufylline to synthesize the enantiopure (R)-hydroxy metabolite: (-)-1,3-dibutyl-7-((2'R)-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione (1). The experimental conditions for the biotransformation were optimized. As denbufylline is insoluble in aqueous media, the influence of cosolvents (dimethylsulfoxide (DMSO), acetonitrile) and different concentrations of each solvent in the reaction mixture on the yield and enantiomeric excess of the final biotransformation product was studied. The maximum biotransformation yield (96-98%) and highest enantioselectivity (96% ee) for the obtained metabolite were reached using DMSO as a cosolvent at a concentration of 7.5% (v/v) in the presence of L. kefiri immobilized either in calcium alginate or in carrageenan. The absolute configuration of the stereogenic center of 1 was determined by applying Mosher's method.

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Section: Methodsmentioning

confidence: 99%

Preparation of enantiopure (R)‐hydroxy metabolite of denbufylline using immobilized Lactobacillus kefiri DSM 20587 as a catalyst

2008

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Halogenopurines

1971

Chemistry of Heterocyclic Compounds: A Series of Monographs

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The Oxo‐(Hydroxy‐) and Alkoxypurines

1971

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Analogs of Nucleotides. I. Theophyllinylalkylphosphonic Acids and Related Compounds¹

Cited by 8 publications

References 0 publications

Preparation of enantiopure (R)‐hydroxy metabolite of denbufylline using immobilized Lactobacillus kefiri DSM 20587 as a catalyst

Preparation of enantiopure (R)‐hydroxy metabolite of denbufylline using immobilized Lactobacillus kefiri DSM 20587 as a catalyst

Halogenopurines

The Oxo‐(Hydroxy‐) and Alkoxypurines

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Analogs of Nucleotides. I. Theophyllinylalkylphosphonic Acids and Related Compounds1

Cited by 8 publications

References 0 publications

Preparation of enantiopure (R)‐hydroxy metabolite of denbufylline using immobilized Lactobacillus kefiri DSM 20587 as a catalyst

Preparation of enantiopure (R)‐hydroxy metabolite of denbufylline using immobilized Lactobacillus kefiri DSM 20587 as a catalyst

Halogenopurines

The Oxo‐(Hydroxy‐) and Alkoxypurines

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Analogs of Nucleotides. I. Theophyllinylalkylphosphonic Acids and Related Compounds¹