N→N Alkyl and Glycosyl Migrations of Purines and Pyrimidines. IV. trans-Glycosylation from Pyrimidines to Purines. (A Novel Synthetic Method of Purine Nucleosides and Nucleotides)

• MIYAKI MICHIKO

• SAITO AKIO

• SHIMIZU BUNJI

Abstract

Application of N³→N⁹(N⁷) migration reaction of purine derivatives led to a novel synthetic procedure of purine nucleosides and nucleotides. Direct transfer of ribosyl moieties of acylated pyrimidine nucleosides, nucleotides and trimethylsilylated nucleotides to purine bases was successfully carried out in the pressence of catalyst. Adenosine, N⁶, N⁶-dimethyladenosine, inosine, guanosine, 7-D-ribofuranosylguanine, 7-D-ribofuranosyl theophylline, adenosine 5'-phosphate, 7-D-ribofuranosyl theophylline 5'-phosphate and other glycosyl derivatives were obtained by transglycosylation reaction. Preparation of purine nucleosides and nucleotides by this transglycosylation reaction must be a valuable method for utilization of useless pyrimidine nucleotides which are produced during degradation of RNA together with useful purine nucleotides as seasoning.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 18 (12), 2459-2468, 1970

  The Pharmaceutical Society of Japan

Keywords

• Drug Discovery
• General Chemistry
• General Medicine

Details

• CRID: 1390001204170512768
• NII Article ID: 110003632251
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.18.2459
• COI: 1:CAS:528:DyaE3MXmsVelsQ%3D%3D
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/18/12/18_12_2459/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1971087457
• Text Lang: en
• Data Source:
  • JaLC
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed