Synthesis and Enzymic Hydrolysis of Acylated Adenosine Derivatives
نویسنده
چکیده
Various derivatives of adenosine were prepared by acylation of adenosine (6-amino-9-(bD-ribofuranosyl)purine (1) with different molar equivalents of acetic anhydride and/or pivaloyl chloride in pyridine. Compounds 6-acetylamino-9-[(2,3,5-tri-O-acetyl)-b-Dribofuranosyl]purine (3), 6-amino-9-[(2,3,5-tri-O-acetyl)-b-D-ribofuranosyl]purine (4), and 6-pivaloylamino-9-[(2,3,5-tri-O-pivaloyl)-b-D-ribofuranosyl]purine (5) were subsequently submitted to hydrolysis catalyzed by a number of hydrolytic enzymes. Regioselective enzymic deacetylation at the primary hydroxyl group of 3 and 4 with butyrylcholinesterase (BChE) produced 6-acetylamino-9-[(2,3-di-O-acetyl)-b-D-ribofuranosyl]purine (9) and 6-amino-9-[(2,3-di-O-acetyl-b-D-ribofuranosyl]purine (10), respectively. All structures were established by H and C NMR spectroscopies.
منابع مشابه
Synthesis of 2'-/3'-0-Acylated Adenine Nucleotide Analogs and Their Interactions in Photophosphorylation
By mono esterification o f 3'(2')-hydroxyl residues o f adenine nucleotides with various carboxylic acids a series o f nucleotide analogs is available including fluorescent and photoaffinity labels. Their chemical synthesis is described. The equilibrium between 2' and 3' esters is determined by NM R spectroscopy, stability o f the esters and their tendency o f acyl migration is discussed. The i...
متن کاملSynthesis and hydrolysis of ADP-arsenate by beef heart submitochondrial particles.
The kinetic parameters for inorganic phosphate and inorganic arsenate as substrates for the synthesis of ATP and ADP-arsenate, respectively, by beef heart submitochondrial particles have been determined. The Vm and Km values for arsenate and phosphate, as well as the Km values for ADP in the two reactions, are the same within experimental error of the measurements. These data are consistent wit...
متن کاملUnexpected Hydrolytic Instability of N-Acylated Amino Acid Amides and Peptides
Remote amide bonds in simple N-acyl amino acid amide or peptide derivatives 1 can be surprisingly unstable hydrolytically, affording, in solution, variable amounts of 3 under mild acidic conditions, such as trifluoroacetic acid/water mixtures at room temperature. This observation has important implications for the synthesis of this class of compounds, which includes N-terminal-acylated peptides...
متن کاملSynthesis of some Novel Chromenopyrimidine Derivatives and Evaluation of Their Biological Activities
AbstractPyrimidine nucleosides are constituents of fundamental structure of the cells. There has been considerable attentions in the chemistry of pyrimidine derivatives due to having a wide range of biological activities such as antiviral, anti-malarial agents, cytostatic, antithelemintic, antibacterial, adenosine receptor ligands, anti-cancer agents, compounds targeting delayed-type hypersensi...
متن کاملSynthesis of some Novel Chromenopyrimidine Derivatives and Evaluation of Their Biological Activities
AbstractPyrimidine nucleosides are constituents of fundamental structure of the cells. There has been considerable attentions in the chemistry of pyrimidine derivatives due to having a wide range of biological activities such as antiviral, anti-malarial agents, cytostatic, antithelemintic, antibacterial, adenosine receptor ligands, anti-cancer agents, compounds targeting delayed-type hypersensi...
متن کامل