- PROCESS FOR THE PREPARATION OF AN (RP)-8-SUBSTITUTED CAMPS
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This invention relates to a process for the preparation of an (Rp)-8-substituted adenosine-3',5'-cyclic phosphorothioic acid, or a salt or ester thereof, which comprises P-amidating 8-bromoadenosine-3',5'-cyclic phosphoric acid, and reacting the P-amidate with a base and with carbon disulphide to yield (Rp)-8-bromoadenosine-3',5'-cyclic phosphorothioic acid or a salt or ester thereof.
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Page/Page column 8-9; 12
(2008/06/13)
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- Stereoselective preparation of (RP)-8-hetaryladenosine-3′, 5′-cyclic phosphorothioic acids
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Cyclic adenosine monophosphate (cAMP) has been converted into its 8-bromo derivative and 2′O-TBDMS protected before activation of the phosphoric acid moiety with a reagent generated in situ from oxalyl chloride and DMF. Further reactions with primary amines furnished corresponding phosphoramidates with high stereoselectivity at the phosphorus atom. Cross-coupling reactions with the 8-bromopurine yielded 8-hetaryl derivatives. X-Ray analyses showed the amidates to possess the (SP)-configuration. Carbon disulfide effected thiylation under strongly basic conditions stereospecifically provided the (RP)-phosphorothioic acids. The Royal Society of Chemistry.
- Andrei, Mioara,Bjornstad, Vidar,Langli, Geir,Romming, Christian,Klaveness, Jo,Tasken, Kjetil,Undheim, Kjell
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p. 2070 - 2080
(2008/03/12)
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- PURINE NUCLEOTIDE DERIVATIVES
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This invention provides novel 8-carbyl substituted cAMPS and a novel procedures for the preparation of 8-Br-cAMP, a key starting material.
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Page/Page column 64
(2010/02/15)
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- Coumarinylmethyl esters for ultrafast release of high concentrations of cyclic nucleotides upon one- and two-photon photolysis
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(Chemical Equation Presented) Shedding light: Efficient activation of cyclic nucleoside monophosphates (cNMPs) can be achieved upon one- and two-photon flash photolysis of novel photolabile coumarinylmethyl esters of cAMP and cGMP (A = adenosine, G = guanosine) as well as their 8-bromosubstituted derivatives. The phototriggers show high solubility in water and permit space- and time-resolved investigations of the molecular mechanisms of cyclic nucleotide dependent processes.
- Hagen, Volker,Dekowski, Brigitte,Nache, Vasilica,Schmidt, Reinhard,Geissler, Daniel,Lorenz, Dorothea,Eichhorst, Jenny,Keller, Sandra,Kaneko, Hiroshi,Benndorf, Klaus,Wiesner, Burkhard
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p. 7887 - 7891
(2007/10/03)
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