Purines. XVIII. Kinetic Studies of the Dimroth Rearrangement of 1-Alkoxy-9-methyladenines and 1-Benzyloxyadenosine : Effect of 1-Benzyloxy and 9-β-D-Ribofuranosyl Groups on the Rates of the Ring-opening and the Reclosure
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概要
- 論文の詳細を見る
Rates of the Dimroth rearrangements of 1-benzyloxyadenosine (Id) and 1-alkoxy-9-methyladenines (Ia-c), which give the rearranged products (IIIa-d) and the deformylated compounds (IVa-d) competitively through the isolable monocyclic intermediates (IIa-d), have been measured at different pH's and ionic strength 1.0 at 40°. It has been shown that all reactions obey good pseudo-first-order kinetics. The ring-opening (I→II) follows the rate law given by k^<(0)>_<II. obsd>[I]_<total>=k^<(0)>_<II. lonie>[I・H^+][OH^-]+k^<(0)>_<II. neit>[I][OH^-] where k^<(0)>_<II. obsd> is the observed limiting rate constant for zero buffer concentration ; [I・H^+] is the concentration of the protonated base ; [I], the concentration of the free base ; [I]_<total>, the sum of [I・H^+] and [I]. Comparison of the individual second-order rate constants thus obtained (Table III) has revealed that attack of hydroxide ion on the protonated species is faster than on the neutral species by a factor of 560-1200 and that both reaction modes are promoted by the β-D-ribofuranosyl substituent at the 9-position. Both the ring-closure (II→III) and the deformylation (II→IV) in 0.1M buffer solutions are enhanced by the β-D-ribofuranosyl group at the 1-position of II, whereas the benzyl group on the O-atom of the amidoxime moiety of II exerts the stabilizing effect on II. The unusually low pK_a's of 9.9 to 10.6 at 40°observed for II have been assigned to the acidic ones of the formamido group of II. Probable mechanisms for the ring-closure and the deformylation of II are also described.
- 公益社団法人日本薬学会の論文
- 1975-11-25
著者
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斎藤 徹
Faculty Of Pharmaceutical Sciences Kanazawa University
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藤井 澄三
Faculty Of Pharmaceutical Sciences Kanazawa University
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板谷 泰助
Faculty of Pharmaceutical Sciences, Kanazawa University
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川勝 哲
Faculty of Pharmaceutical Sciences, Kanazawa University
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川勝 哲
Faculty Of Pharmaceutical Sciences Kanazawa University
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