Studies of nucleosides and nucleotides—LIV

Ikehara, Morio; Ogiso, Yuko

doi:10.1016/s0040-4020(01)93816-5

Cited by 28 publications

(10 citation statements)

References 22 publications

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“…The resulting solid was dissolved in cold water (2 ml) and stirred at 0 "C for 2 h. Both 8,2'-thioanhydroadenosine 5'-monophosphate (2a) and 8,2'-thioanhydroinosine 5'-monophosphate (2c) precipitated upon addition of excess ethanol. The yield of 2a was 236 mg (92%) a n d the product was identical to that prepared as in the literature (6). The yield of 2c was 188 mg (74%).…”

Section: Synthesis Of 82'-thioani1ydropurir7e N~rcleoside 5'-supporting

confidence: 69%

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Synthesis of Nucleotides from 8,2′-Thioanhydropurine Nucleosides

Ogilvie¹,

Slotin²

1973

Can. J. Chem.

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The 5′-mono and diphosphates of the common 8,2′-thioanhydropurine nucleosides have been prepared and studied with 5′-nucleotidase. alkaline phosphatase, and adenylate kinase. Procedures for the preparation of protected anhydronucleosides and their incorporation into dianhydronucleoside monophosphates have been developed. These nucleotides have been found to be completely resistant to spleen and snake venom phosphodiesterases but are readily converted with Raney nickel into the natural 2′-deoxy-nucleotides.

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Section: Synthesis Of 82'-thioani1ydropurir7e N~rcleoside 5'-supporting

confidence: 69%

“…2a was obtained in 92% yield and was identical to an authentic sample prepared by cyclization of 2'-0-tosyl-8-bromoadenosine 5'-phosphate (6). The structure of 2a was further confirmed by Raney nickel reduction to 2'-deoxyadenosine 5'-phosphate which was dephosphorylated with 5'-nucleotidase to give 2'-deoxyadenosine.…”

Section: Resultsmentioning

confidence: 67%

Synthesis of Nucleotides from 8,2′-Thioanhydropurine Nucleosides

Ogilvie¹,

Slotin²

1973

Can. J. Chem.

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“…8 . 9 ) Although the synthesis of ara-A has been achieved by means of a sugar-base coupling reaction, cleavage reaction of 8,2' -anhydro-8-oxo-9-p-D-arabinofuranosyladenine or transformation of an oxazolidine thione derivative, 10.11) there remain some definite practical limitations to these approaches because of the low-yielding, laborious and time-consuming process. In the previous paper,12) we reported the introduction of new method-Recently, the antiviral activity of ara-A has generated considerable interest and made it the target of extensive chemotherapeutic and biological investigations.…”

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confidence: 99%

Microbiological Synthesis of Adenine Arabinoside

Utagawa¹,

Morisawa²,

Yoshinaga³

et al. 1985

Agricultural and Biological Chemistry

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The microbiological synthesis of 9-p-D-arabinofuranosyl adenine (ara-A, an antiviral drug) from adenine and arabinofuranosyluracil (ara-U) is described. Various bacteria, especially Enterobacter aerogenes. Escherichia coli, Erwinia herbicola and Aeromonas salmonicida, were found to be able to transfer the arabinofuranosyl moiety of ara-U to adenine (transarabinosylation) in the presence of inorganic phosphate. The optimum conditions for the transarabinosylation were pH 7.0 and 60°C. No reaction was observed in the absence of inorganic phosphate and its optimum concentration was around 30 mM. Six grams of ara-A was produced in liter of reaction mixture in the presence of wet cell paste of Enterobacter aerogenes AJ 11125. Ara-A formed was precipitated in the reaction mixture and isolated with an 87% yield. Physicochemical data for the compound agreed with those of authentic ara-A.

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“…(639) A similar reaction was found to occur with the 8,3'-cyclonucleoside. Ring opening of (582) with sodium azide occurs at the 2' position to give 2'-azido-8-oxoadenosine(ribo configuration).…”

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confidence: 63%

“…This result was rationalized by invoking an initial formation of the sulfonium intermediate (600). (641) Another interesting rearrangement occurred as a result of chloride attack on …”

mentioning

confidence: 99%