634-01-5Relevant articles and documents
Synthesis of adenosine cyclic 3′,5′ -phosphorofuoridate (camp-f)
Baraniak, Janina,Stec, Wojciech J.,Blackburn, G. Michael
, p. 8119 - 8122 (1995)
Work aimed at the chiral synthesis of both diastereomers of adenosine cyclic 3′,5′phosphorofluoridate, cAMP-F 7, is described. Attempted debenzoylation of the intermediate N6,N6,O2′tribenzoyladenosine cyclic 3′,5′-phosphorofluoridate 4 by ammonolysis resulted in cleavage of the P-F bond. Reaction of [Sp]-S-methyl adenosine 3′,5′-cyclophosphorothioate 6 with AgF gives a mixture of the two diastereoisomers of the cyclic phosphore fluoridate 7 along with adenosine 2′ ,3′-cyclic phosphate 8. The conversion of 7 into 8 can be completed under remarkably mild conditions. Possible mechanisms for this unusual transformation are discussed.
The Stereochemical Course of Substitution of Sulfur by Oxygen Nucleophiles in Five-membered Cyclic Phosphorothioates
Lowe, Gordon,Thelin, Mats
, p. 1947 - 1948 (1994)
The replacement of non-bridging sulfur in five-membered cyclic phosphorothioates by oxygen nucleophiles in the presence of bromine occurs with retention of configuration and has allowed the 31P NMR signals of the diastereoisomeric tert-butyldiphenyl silyl esters of 2',3'-cyclic adenosine monophosphate to be assigned.
Harnessing chemical energy for the activation and joining of prebiotic building blocks
Liu, Ziwei,Wu, Long-Fei,Xu, Jianfeng,Bonfio, Claudia,Russell, David A.,Sutherland, John D.
, p. 1023 - 1028 (2020/10/26)
Life is an out-of-equilibrium system sustained by a continuous supply of energy. In extant biology, the generation of the primary energy currency, adenosine 5′-triphosphate and its use in the synthesis of biomolecules require enzymes. Before their emergence, alternative energy sources, perhaps assisted by simple catalysts, must have mediated the activation of carboxylates and phosphates for condensation reactions. Here, we show that the chemical energy inherent to isonitriles can be harnessed to activate nucleoside phosphates and carboxylic acids through catalysis by acid and 4,5-dicyanoimidazole under mild aqueous conditions. Simultaneous activation of carboxylates and phosphates provides multiple pathways for the generation of reactive intermediates, including mixed carboxylic acid–phosphoric acid anhydrides, for the synthesis of peptidyl–RNAs, peptides, RNA oligomers and primordial phospholipids. Our results indicate that unified prebiotic activation chemistry could have enabled the joining of building blocks in aqueous solution from a common pool and enabled the progression of a system towards higher complexity, foreshadowing today’s encapsulated peptide–nucleic acid system. [Figure not available: see fulltext.].
Cleavage of short oligoribonucleotides by a Zn2+binding multi-nucleating azacrown conjugate
Laine, Maarit,L?nnberg, Tuomas,Helkearo, Mia,L?nnberg, Harri
, p. 111 - 117 (2016/10/04)
A multi-nucleating azacrown conjugate (5a) consisting of two 3,5-bis(1,5,9-triazacyclododecan-3-yloxymethyl)benzyl groups attached to 1 and 7 sites of cyclen was prepared and tested as an artificial ribonuclease. The conjugate in the presence of five equivalents of zinc nitrate expectedly showed uridine selectivity comparable to that 1,3,5-tris(1,5,9-triazacyclododecan-3-yl)benzene (2), a compound known to bind to two adjacent uridine residues and cleave the intervening phosphodiester bond. 5a was, however, unable to discriminate between two and three adjacent uridine residues, but cleaved oligonucleotides containing a UpU and UpUpU site at a comparable rate, even when present at sub-saturating concentrations.
