Studies of nucleosides and nucleotides—XLV

Ikehara, Morio; Kaneko, Masakatsu; Okano, Ruiko

doi:10.1016/0040-4020(70)80003-5

Cited by 26 publications

(4 citation statements)

References 13 publications

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“…Purine riboside 3′,5′-cyclic monophosphate (cPMP) was synthesized from purine riboside (Aldrich) according to the procedure of Genieser et al (28). The adenosine analogs 8,5′-Ocycloadenosine and N 3 ,5′-cycloadenosine were synthesized according to the procedures of Ikehara et al (29) and Verheyden and Moffatt (30), respectively. The radionucleotides [R-32 P]UTP and [γ-32 P]ATP were purchased from Amersham, and [ 32 P]cAMP was purchased from ICN.…”

Section: Methodsmentioning

confidence: 99%

Molecular Recognition of cAMP by an RNA Aptamer

Koizumi

Breaker

2000

Biochemistry

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Two classes of RNA aptamers that bind the second messenger adenosine 3',5'-cyclic monophosphate (cAMP; 1) were isolated from a random-sequence pool using in vitro selection. Class I and class II aptamers are formed by 33- and 31-nucleotide RNAs, respectively, and each is comprised of similar stem-loop and single-stranded structural elements. Class II aptamers, which dominate the final selected RNA population, require divalent cations for complex formation and display a dissociation constant (K(D)) for cAMP of approximately 10 microM. A representative class II aptamer exhibits substantial discrimination against 5'- and 3'-phosphorylated nucleosides such as ATP, 5'-AMP, and 3'-AMP. However, components of cAMP such as adenine and adenosine also are bound, indicating that the adenine moiety is the primary positive determinant of ligand binding. Specificity of cAMP binding appears to be established by hydrogen bonding interactions with the adenine base as well as by steric interactions with groups on the ribose moiety. In addition, the aptamer recognizes 8,5'-O-cycloadenosine (2) but not N(3), 5'-cycloadenosine (3), indicating that this RNA might selectively recognize the anti conformation of the N-glycosidic bond of cAMP.

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Section: Methodsmentioning

confidence: 99%

Molecular Recognition of cAMP by an RNA Aptamer

Koizumi

Breaker

2000

Biochemistry

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“…As the tosylate method is usually not suitable for the synthesis of purine cyclonucleosides bearing an 8,5′- O -linkage, leading in most cases to N 3 ,5′-cyclonucleosides, a new, complementary method was developed independently and published simultaneously by Ikehara and Nagpal . Using the sulfonate method, the cyclonucleosides are formed by the nucleophilic attack of a keto, thioketo, or N-containing group in the heterocyclic bases at the electron-deficient carbon atom bearing the leaving (arylsulfonyl)oxy group.…”

Section: Synthesis Of Purine Cyclonucleosidesmentioning

confidence: 99%

Preparation of Cyclonucleosides

2009

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“…(396) The synthetic utility of 8,2'-anhydro-8-oxypurine nucleosides has proved substantial. Mild acid treatment of 8,2'-anhydro-8-oxyadenosine (582) (626) Additionally, treatment of 8,2'-anhydro-9-p-o-arabinofuranosyladenine cyclic 3',5'-phosphate (593) with ammonia or sodium methoxide gave the 8-amino and 8-methoxy derivatives of 9-p-o-arabinofuranosyladenine cyclic 3',5'-phosphate (594), (638) respectively. Some interesting rearrangements have been observed for the cyclonucleosides.…”

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confidence: 99%