Method for purification and synthesis of RNA molecules and enzymatic RNA molecules in enzymatically active form.

Synthesis, deprotection, analysis and purification of RNA and ribozymes

Acyclic nucleotide analogues: synthesis, antiviral activity and inhibitory effects on some cellular and virus-encoded enzymes in vitro.

Synthesis Of Nucleosides

A method for the deprotection of RNA comprising reacting an alkylamine or ammonium hydroxide/alkylamine mixture with the RNA at 60-70 degrees Centigrade for 5 to 15 minutes in order to remove any exocyclic protecting groups, wherein said alkylamine is selected from the group consisting of ethylamine, propylamine, and butylamine.

Deprotection of RNA with alkylamine

Phylogenetically invariant G.U wobble pairs are present in a wide variety of RNA's. As a means to study the contribution of individual chemical groups within a G.U pair, we have synthesized and thermodynamically characterized oligoribonucleotides containing the unnatural nucleosides 2,6-diaminopurine riboside (DAP) and 5-methylisocytidine (MeiC). The DAP.MeiC pair at the end of an RNA duplex is as stable as a G.U pair, consistent with formation of a wobble base pair with two hydrogen bonds. DAP.MeiC is a valuable substitution for the study of G.U wobble pairs because it is conformationally similar to the G.U pair, but has a different array of functional groups in the major and minor grooves of the duplex and a reversed hydrogen bonding polarity between the bases. We also report the stability of several other terminal pairs proposed to be in a wobble configuration including inosine.U (I.U), A.MeiC, DAP.C, A.C, G.5-methyl-U,2'-deoxyguanosine.U, and 2'-deoxy-7-deazaguanosine.U. These pairs present a diversity of functional group substitutions in the context of a wobble conformation. Comparison of wobble pairs with and without the N2 exocyclic amine, i.e., G.U vs I.U, DAP.MeiC vs A.MeiC, and DAP.C vs A.C, demonstrates that the amine does not contribute to base pairing stability when the pair is located at the terminal position of the RNA duplex. However, at a position internal to the duplex, the exocyclic amine does improve helix stability. An internal I.U pair is less stable (approximately 1 kcal.mol-1) than an internal G.U pair, and substantially less stable (approximately 2 kcal.mol-1) than an internal A-U pair. These data provide quantitation for the reduced duplex stability observed upon conversion of A-U to I.U pairs by double-stranded RNA adenosine deaminase (dsRAD). This collection of wobble pairs will help identify the contribution made by individual functional groups in RNA/protein interactions and in the tertiary folding of RNA.

The 2,6-diaminopurine riboside.5-methylisocytidine wobble base pair: an isoenergetic substitution for the study of G.U pairs in RNA.

Sont decrites 3 approches permettant l'acces a des derives nucleosides monoinsatures en 2', 3' et ensuite didesoxydes en 2', 3', a partir des precurseurs dihydroxy-2', 3' correspondants (ribonucleosides). Ces methodes sont: la reaction de Lorey-Winter, la formation d'olefines a partir d'orthoesters cycliques, l'elimination reductrice d'halogenoacetates

Preparation of 1-(2,3-dideoxy-.beta.-D-glycero-pent-2-enofuranosyl)thymine (d4T) and 2',3'-dideoxyadenosine (ddA): general methods for the synthesis of 2',3'-olefinic and 2',3'-dideoxy nucleoside analogs active against HIV

Synthesis of (S)-N1-(3-hydroxy-2-phosphonylmethoxy)propylcytosine, (S)-HPMPC

Treatment of uridine (1) with acetyl bromide produced bromoacetate 2 which was reduced with Zn/Cu to give the 2′,3′-unsaturated uridine (d4U; 3). Conversion of the uracil moiety of 3 to thioamide 7 with Lawesson's reagent, followed by amination and deprotection with methanolic ammonia, afforded d4C (9). This multigram scale process for the synthesis of d4C proceeded in 20% yield from uridine.

The use of acetyl bromide for the multigram synthesis of the anti-HIV agent 2',3'-didehydro-2',3'-dideoxycytidine (d4C)

The synthesis of 2′,3′-dideoxyinosine (ddI, 1) from 2′-deoxyinosine and 2′,3′-dideoxyadenosine (ddA, 2) is described. Chemically, selective benzoylation of the 5′ hydroxyl group of 2′-deoxyinosine is followed by deoxy-genation at the 3′ position via the thioimidazolide 4. De-protection of the resulting 5′-O-benzoyl-2′,3′-dideoxyinosine 5 gave 2′,3′-dideoxyinosine 1. Enzymatically, deamination of ddA 2 with adenosine deaminase also yielded ddI.

Synthesis of 2′,3′-Dideoxyinosine

The ring opening of the O-2,3′-anhydrothymidine 5 with the anion of methyl mercaptan gave the 3′-methylthio derivaative 6. Subsequent oxidation and deprotection afforded 3′-(methyl-sulfinyl)-3′-deoxythymidine 2 and its sulfone analogue 3.

A Short Syhthesis of 3′-(Methylsulfinyl)-3′-Deoxythymidine and Related Analogues

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