PMID- 1250701
OWN - NLM
STAT- MEDLINE
DCOM- 19760430
LR  - 20190501
IS  - 0305-1048 (Print)
IS  - 1362-4962 (Electronic)
IS  - 0305-1048 (Linking)
VI  - 3
IP  - 1
DP  - 1976 Jan
TI  - 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.
PG  - 237-50
AB  - 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.
FAU - Okutsu, M
AU  - Okutsu M
FAU - Yamazaki, A
AU  - Yamazaki A
LA  - eng
PT  - Journal Article
PL  - England
TA  - Nucleic Acids Res
JT  - Nucleic acids research
JID - 0411011
RN  - 0 (Imidazoles)
RN  - 0 (Ribonucleosides)
RN  - 12133JR80S (Guanosine)
SB  - IM
MH  - Guanosine/*chemical synthesis
MH  - Imidazoles
MH  - Methods
MH  - Ribonucleosides
PMC - PMC342891
EDAT- 1976/01/01 00:00
MHDA- 1976/01/01 00:01
CRDT- 1976/01/01 00:00
PHST- 1976/01/01 00:00 [pubmed]
PHST- 1976/01/01 00:01 [medline]
PHST- 1976/01/01 00:00 [entrez]
AID - 10.1093/nar/3.1.237 [doi]
PST - ppublish
SO  - Nucleic Acids Res. 1976 Jan;3(1):237-50. doi: 10.1093/nar/3.1.237.