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9-(Aminoalkyl)-8-hydroxyadenines: Preparation, mechanism of formation and use in affinity chromatography of S-adenosyl-L-homocysteine hydrolase
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1986
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8-Bromoadenine DerivativesBioorganic ChemistryEngineeringOrganic ChemistryEnzymatic ModificationCompounds ViiBiosynthesisAffinity ChromatographyDilute Adenosine SolutionStereoselective SynthesisAldehyde DehydrogenaseBiochemistryPharmacologyNatural Product SynthesisEnantioselective SynthesisBiomolecular EngineeringNatural SciencesS-adenosyl-l-homocysteine HydrolaseSynthetic Chemistry
Bromine reacts with 9-(2-hydroxyethyl)- ( Va ), 9-(3-hydroxypropyl)- ( Vb ), 9-(2-hydroxypropyl)- ( Vc ), 9-(2,3-dihydroxypropyl)- ( Vd ), 9-(1,3-dihydroxy-2-propyl)- ( Ve ), 9-threo-(2,3-dihydroxybutyl)- ( Vf ) and 9-threo-(2,3,4-trihydroxybutyl)adenine ( Vg ) to give 8-bromoadenine derivatives ( Vl ). Reaction of compounds Vl with ammonia results in intramolecular cyclization to five- and six-membered cyclic esters which are regiospecifically opened to afford the respective 2-amino-alkyl-8-hydroxyadenines ( VIIa, b ) and 3-aminoalkyl-8-hydroxyadenines ( VIIc-VIIf ). Binding of compounds VII to CH-Sepharose 4B led to the polymeric material XIII capable of binding S-adenosyl-L-homocysteine hydrolase. Compounds XIII derived from the amino derivatives VIIa, b, d are of affinity support character and liberate the enzyme only on elution with dilute adenosine solution.