Polynucleotides. XII. Synthesis and Properties of Dinucleoside Monophosphates containing 8-Bromoadenosine
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概要
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Attempt to obtain 8-bromoadenylyl-(3'-5')-8-bromoadenosine (BrApBrA) (III) by the condensation of N^6,O^<2'>, O^<3'>-tribenzoyl-8-bromoadenosine 3'-phosphate (V) and 2', 3'-O-ethoxymethylidene-8-bromoadenosine (VI) using dicyclohexylcarbodiimide (DCC) gave 8-oxyadenylyl-(3'-5')-8-bromoadenosine (HOApBrA) (VII) after removal of protecting groups. Structure of VII was confirmed by ultraviolet (UV) and circular dichroism (CD) spectra as well as enzymatic hydrolysis. Condensation of N^6,O^5-diacetyl-8-bromoadenosine 2'(3')-phosphate (IVa) and compound VI using diphenylphosphorochloridate gave 2'-5'(X) and 3'-5'(III) isomers of 8-bromoadenylyl-8-bromoadenosine, which were separated and purified by column chromatography, paper electrophoresis and paper chromatography. Structure of compounds X and III was elucidated by optical properties and enzymatic digestions. Hypochromicities of X and III were 14% and 10%, respectively. From the CD spectra of both compounds, a syn-syn, left-handed structure of these dinucleoside monophosphates was predicted.
- 公益社団法人日本薬学会の論文
- 1972-11-25
著者
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上杉 晴一
Faculty Of Engineering Yokohama National University
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池原 森男
Faculty of Pharmaceutical Sciences, Osaka University(Present address)
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小林 真由美
Faculty Of Pharmaceutical Sciences Osaka University
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池原 森男
Faculty Of Pharmaceutical Sciences Osaka University
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上杉 晴一
Faculty Of Pharmaceutical Sciences Osaka University
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