ChemInform Abstract: HOMOLYTISCHE C‐METHYLIERUNG VON GUANIN, GUANOSIN UND GUANYLSAEURE

Kawazoe, Yutaka; Maeda, Momoe; Nushi, K.

doi:10.1002/chin.197242334

Cited by 3 publications

(3 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This reaction, however, has been virtually uninvestigated in the field of biologically significant heterocycles. Only recently Kawazoe et al (1972) have examined homolytic methylation of guanine, guanosine, and 5'-guanylic acid and found that 8-methylguanine was produced from the action of guanine, tert-butyl hydroperoxide, and FeS04, in the presence of dilute sulfuric acid.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and enzymic activity of 8-acyl and 8-alkyl derivatives of guanosine 3',5'-cyclic phosphate

Christensen¹,

Meyer²,

Miller³

et al. 1975

Biochemistry

View full text Add to dashboard Cite

Several new 8-alkyl and 8-acyl derivatives of quanosie 3',5'-cyclic phosphate (cGMP) and inosine 3',5'-cyclic phosphate (cGMP) were prepared by direct alkylation or acylation of the parent cyclic nucleotide via free radicals generated in situ. These compounds have been examined for their ability to stimulate a cGMP-dependent protein kinase, and several of the cGMP derivatives were as active in this regard as cGMP. These compounds proved to be quite ineffective when tested for their ability to activate an adenosine 3',5'-cyclic phosphate (cAMP) dependent protein kinase. In addition, these 8-substituted cGMP derivatives are not substrates for a phosphodiesterase preparation from rabbit kidney, but do show inhibition of the hydrolysis of cAMP by crude phosphodiesterase preparations from rabbit lung and beef heart.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and enzymic activity of 8-acyl and 8-alkyl derivatives of guanosine 3',5'-cyclic phosphate

Christensen¹,

Meyer²,

Miller³

et al. 1975

Biochemistry

View full text Add to dashboard Cite

show abstract

“…(G) 7,8-Dimethyl-9-(4'-hydroxy-2'-oxabut-1 '-yl)guanine 4'-Phosphate (m^acycloGMP, 7). 8-Methylacycloguanosine was prepared from acycloG essentially as described earlier (Kawazoe et al, 1972). A total of 500 mg of acycloG (2.21 mmol) was dissolved in 100 mL of 0.2 N H2S04 containing 2 g of FeS04-7H20 (7.2 mmol) at room temperature.…”

Section: Methodsmentioning

confidence: 99%

Inhibition of eukaryotic translation by analogs of messenger RNA 5'-cap: chemical and biological consequences of 5'-phosphate modifications of 7-methylguanosine 5'-monophosphate

Darżynkiewicz¹,

Ekiel²,

Lassota³

et al. 1987

Biochemistry

View full text Add to dashboard Cite

New analogues of 7-methylguanosine 5'-monophosphate (m7GMP) were synthesized with modified 5'-phosphate moieties by replacement of -O with -H, -CH3, or -NH2. Additional analogues were synthesized with 8-methyl- or 8-aminoguanine base substitutions or ring-opened ribose (2',3'-diol). These compounds were analyzed by 1H and 31P NMR for solution conformation. In addition, they were also analyzed for biological activity as analogues of mRNA 5'-caps by competition as inhibitors of translation in reticulocyte lysate. Substitution of oxygen on the 5'-monophosphate moiety by -H and -CH3 diminished the activity of the cap analogue as a competitive inhibitor; however, replacement by -NH2 did not diminish the activity of the analogue as an inhibitor. It was inferred from this result that cap binding proteins require a hydrogen bond acceptor as opposed to having an exclusive requirement for a second anionic group on the alpha-phosphate moiety. Inhibition results obtained with C8-substituted m7GMP analogues indicated that the 8-amino derivative was a better inhibitor than the 8-methyl derivative of m7GMP. The former is primarily anti whereas the latter is primarily syn with respect to glycosidic bond conformation. This result further supports the model that the anti conformation is the preferred form of the cap structure for interaction with cap binding proteins. The 2',3'-diol derivative of m7GMP was inactive as an inhibitor of translation.

show abstract

“…(580) Diethyl pyrocarhonatc has also been shown to cause a similar degradation of guanosine (371) at pH 6. The }(2 of guanosine was not acylated under these conditions, and the only product (40 %) was 2-amino-5-ethoxycarbonylamino-4-hydroxy-6-(fl-o-ribofuranosylamino )pyrimidine (542). (581) A most interesting rearrangement was observed when 6-cyano-9-(2,3,5-tri-Oacetyl-fJ-o-ribofuranosyl)purine (543) was treated with methanolic ammonia in an attempt to form purine-6-carboxamidine nucleoside.…”

Section: By Nucleophilicmentioning

confidence: 96%

Synthesis and Properties of Purine Nucleosides and Nucleotides

Srivastava

Robins²,

Meyer

1988

Chemistry of Nucleosides and Nucleotides

View full text Add to dashboard Cite

ChemInform Abstract: HOMOLYTISCHE C‐METHYLIERUNG VON GUANIN, GUANOSIN UND GUANYLSAEURE

Cited by 3 publications

References 1 publication

Synthesis and enzymic activity of 8-acyl and 8-alkyl derivatives of guanosine 3',5'-cyclic phosphate

Synthesis and enzymic activity of 8-acyl and 8-alkyl derivatives of guanosine 3',5'-cyclic phosphate

Inhibition of eukaryotic translation by analogs of messenger RNA 5'-cap: chemical and biological consequences of 5'-phosphate modifications of 7-methylguanosine 5'-monophosphate

Synthesis and Properties of Purine Nucleosides and Nucleotides

Contact Info

Product

Resources

About