- A one-pot, water compatible synthesis of pyrimidine nucleobases under plausible prebiotic conditions
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Herein, we report a new prebiotically plausible pathway towards a pyrimidine nucleobase in continuous manner. The route involves simultaneous methylation and carbamoylation of cyanoacetylene-derived α,β-unsaturated thioamide with N-methyl-N-nitrosourea (MNU) in aqueous media. This provides S-methylpyrimidinone in one-pot, which can be converted into a variety of 4-substituted pyrimidine nucleobases including cytosine and uracil.
- Okamura, Hidenori,Becker, Sidney,Tiede, Niklas,Wiedemann, Stefan,Feldmann, Jonas,Carell, Thomas
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supporting information
p. 1939 - 1942
(2019/05/02)
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- Substrate specificity of E. coli uridine phosphorylase. Further evidences of high-syn conformation of the substrate in uridine phosphorolysis
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Twenty five uridine analogues have been tested and compared with uridine with respect to their potency to bind to E. coli uridine phosphorylase. The kinetic constants of the phosphorolysis reaction of uridine derivatives modified at 2′-, 3′- and 5′-positions of the sugar moiety and 2-, 4-, 5- and 6-positions of the heterocyclic base were determined. The absence of the 2′- or 5′-hydroxyl group is not crucial for the successful binding and phosphorolysis. On the other hand, the absence of both the 2′- and 5′-hydroxyl groups leads to the loss of substrate binding to the enzyme. The same effect was observed when the 3′-hydroxyl group is absent, thus underlining the key role of this group. Our data shed some light on the mechanism of ribo- and 2′-deoxyribonucleoside discrimination by E. coli uridine phosphorylase and E. coli thymidine phosphorylase. A comparison of the kinetic results obtained in the present study with the available X-ray structures and analysis of hydrogen bonding in the enzyme-substrate complex demonstrates that uridine adopts an unusual high-syn conformation in the active site of uridine phosphorylase.
- Alexeev,Sivets,Safonova,Mikhailov
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p. 107 - 121
(2017/02/05)
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- FUSED HETEROARYL DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS
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Fused heteroaryl derivative compounds which are antagonists of orexin receptors are provided. The compounds can be used in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. Also provided is a composition which comprises the compound can be use to prevent or treat such diseases in which orexin receptors are involved.
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Page/Page column 105
(2016/07/27)
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- Synthesis of 1-[cis-3-(hydroxymethyl)cyclobutyl]-uracil, -thymine and -cytosine
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4-(Benzylsulfanyl)pyrimidin-2(1H)-one 6a is prepared from 1-benzoyluracil 10a in three steps and in satisfactory overall yield. Reproducible conditions are found for the cycloaddition reaction between allyl benzyl ether and dichloroketene, leading to the
- Frieden, Miriam,Giraud, Matthieu,Reese, Colin B.,Song, Quanlai
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p. 2827 - 2832
(2007/10/03)
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- Artificial DNA base pair analogues
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The present invention is directed to new artificial base pairs comprising complementary artificial purines and pyrimidines and methods of using artificial complementary base pairs.
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- A Rapid and Efficient Synthesis of Sulfur Analogues of Pyrimidine Bases
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An improved procedure for thionation of some natural pyrimidine bases with tetraphosphorus decasulfide/sodium hydrogen carbonate is reported.Some substituted uracils and 2-thiouracils were converted into a series of analogues in which the oxygen at position 4 was replaced by sulfur atom.The advantage of this method of thionation over the older procedures is based on the tetraphosphorus decasulfide/sodium hydrogen carbonate mixture giving rise to excellent yields and simplified isolation of the desired pure products.
- Lapucha, Andrzej R.
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p. 256 - 258
(2007/10/02)
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- Bis-s-triazolopyrimidine and Some Simple Derivatives
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A general synthetic route to the new tricyclic system bis-s-triazolopyrimidine, is reported.Thus the parent heterocycle (11a) is prepared from the key bicyclic intermediate, s-triazolopyrimidin-5-ylamine (7a), through the correspondi
- Brown, Desmond J.,Shinozuka, Kazuo
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p. 1147 - 1152
(2007/10/02)
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