A new synthesis of 5'-deoxy-8,5'-cyclo-adenosine and -inosine: conformationally-fixed purine nucleosides (nucleosides and nucleotides XVI) | Zendy

Akira Matsuda | Zendy; Kei Muneyama | Zendy; Takashi Nishida | Zendy; Tsutomu Sato | Zendy; Takuya Ueda | Zendy

Open Access

A new synthesis of 5'-deoxy-8,5'-cyclo-adenosine and -inosine: conformationally-fixed purine nucleosides (nucleosides and nucleotides XVI)

Author(s) -

Akira Matsuda,

Kei Muneyama,

Takashi Nishida,

Tsutomu Sato,

Takuya Ueda

Publication year - 1976

Publication title -

nucleic acids research

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 9.008

H-Index - 537

eISSN - 1362-4954

pISSN - 0305-1048

DOI - 10.1093/nar/3.12.3349

Subject(s) - inosine , adenosine , purine , yield (engineering) , nucleotide , derivative (finance) , stereochemistry , purine metabolism , biology , chemistry , biochemistry , enzyme , materials science , gene , financial economics , economics , metallurgy

A versatile method for the synthesis of 5'-deoxy-8,5'-cycloadenosine, a conformationally-fixed "anti" type of adenosine, was presented. Irradiation of 2', 3'-O-isopropylidene-5'-deoxy-5'-phenylthioadenosine with 60W Hg vapor lamp afforded 2',3'-O-isopropylidene-5'-deoxy-8,5'-cycloadenosine in high yield. The use of other 5'-alkylthio derivatives also gave the cycloadenosine, though the yields were rather poor. Deacetonation of the cyclocompound with 0.1N HCl gave 5'-deoxy-8,5'-cycloadenosine. The cycloinosine derivative was similarly prepared. The nmr, mass and CD spectra of 5'-deoxy-8,5'-cycloadenosine were given and discussed with the previously reported results.

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