Skip to main content
NCBI home page
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1976 Jan;3(1):237–250. doi: 10.1093/nar/3.1.237

Synthesis of guanosine and its derivatives from 5-amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide. III. Formation of a novel cycloimidazole nucleoside and its cleavage reactions.

M Okutsu, A Yamazaki
PMCID: PMC342891  PMID: 1250701

Abstract

A new cycloimidazole nucleoside, 5-(1 inch -benzamido-1 inch-hydroxymethylene) amino-2', 1 inch-anhydro-1-beta-D-ribofuranosyl-4-imidazolecarboxamide (III) was synthesized by reaction of 5-amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide (AICA-riboside) with benzoyl isothiocyanate followed by methylation with methyl iodide. The structure of III was elucidated on the basis of its nmr spectra and chemical reactions. Of special interest are reactions of III with various nucleophiles. For example, guanosine (IX) was obtained by amination of III wtih ammonia in 72% yield. Analogous reactions of III with methylamine and dimethylamine gave N2-methylguanosine (X) and N2-dimethylguanosine (XI), respectively. Refluxing of III in alkaline solution afforded xanthosine (VII). The probable mechanism of formation and facile ring-opening of III is also discussed.

Full text

PDF
237

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. FOX J. J., WEMPEN I. Pyrimidine nucleosides. Adv Carbohydr Chem. 1959;14:283–380. doi: 10.1016/s0096-5332(08)60226-x. [DOI] [PubMed] [Google Scholar]
  2. GERSTER J. F., ROBINS R. K. PURINE NUCLEOSIDES. X. THE SYNTHESIS OF CERTAIN NATURALLY OCCURRING 2-SUBSTITUTED AMINO-9-BETA-D-RIBOFURANOSYLPURIN-6(1H)-ONES (N2-SUBSTITUTED GUANOSINES). J Am Chem Soc. 1965 Aug 20;87:3752–3759. doi: 10.1021/ja01094a037. [DOI] [PubMed] [Google Scholar]
  3. Gerster J. F., Robins R. K. Purine nucleosides. 8. The synthesis of 2-fluoro- and 2-chloroinosine and certain derived purine nucleosides. J Org Chem. 1966 Oct;31(10):3258–3262. doi: 10.1021/jo01348a037. [DOI] [PubMed] [Google Scholar]
  4. Kusashio K., Yoshikawa M. Studies of phosphorylation. II. Reaction of 2',3'-O-isopropylideneinosine and -guanosine with phosphoryl chloride. Bull Chem Soc Jpn. 1968 Jan;41(1):142–149. doi: 10.1246/bcsj.41.142. [DOI] [PubMed] [Google Scholar]
  5. STRAUS D. B., FRESCO J. R. SYNTHESIS OF N-BENZOYL-2'-O-TETRAHYDROPYRANYLGUANOSINE-5'-PHOSPHATE, AN INTERMEDIATE IN THE CHEMICAL SYNTHESIS OF POLYRIBOGUANYLIC ACID. J Am Chem Soc. 1965 Mar 20;87:1364–1374. doi: 10.1021/ja01084a035. [DOI] [PubMed] [Google Scholar]
  6. TAKAMIZAWA A., HIRAI K., TORI K. ISOLATION OF CIS- AND TRANS-2METHOXYMETHYLENE-3-ETHOXYPROPIONITRILE. Chem Pharm Bull (Tokyo) 1963 Sep;11:1212–1214. doi: 10.1248/cpb.11.1212. [DOI] [PubMed] [Google Scholar]
  7. Yamazaki A., Kumashiro I., Takenishi T. Synthesis of guanosine and its derivatives from 5-amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide. II. Ring closure with sodium methylxanthate. J Org Chem. 1967 Oct;32(10):3032–3038. doi: 10.1021/jo01285a021. [DOI] [PubMed] [Google Scholar]
  8. Yamazaki A., Kumashiro I., Takenishi T. Synthesis of guanosine and its derivatives from 5-amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide. II. Ring closure with sodium methylxanthate. J Org Chem. 1967 Oct;32(10):3032–3038. doi: 10.1021/jo01285a021. [DOI] [PubMed] [Google Scholar]
  9. Yamazaki A., Kumashiro I., Takenishi T. Synthesis of guanosine and its derivatives from 5-amino-1-beta-d-ribofuranoxyl-4-imidazolecarboxamide. I. Ring closure with benzoyl isothiocyanate. J Org Chem. 1967 Jun;32(6):1825–1828. doi: 10.1021/jo01281a027. [DOI] [PubMed] [Google Scholar]
  10. Yoshikawa M., Kato T., Takenishi T. A novel method for phosphorylation of nucleosides to 5'-nucleotides. Tetrahedron Lett. 1967 Dec;50:5065–5068. doi: 10.1016/s0040-4039(01)89915-9. [DOI] [PubMed] [Google Scholar]

Articles from Nucleic Acids Research are provided here courtesy of Oxford University Press

RESOURCES