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Acyclic nucleic acid analogues synthesis and oligomerization of gamma 4 diamino 2 oxo 1 2h pyrimidinepentanoic acid and delta 4 diamino 2 oxo 1 2h pyrimidinehexanoic acid

Acyclic nucleic acid analogues synthesis and oligomerization of gamma 4 diamino 2 oxo 1 2h pyrimidinepentanoic acid and delta 4 diamino 2 oxo 1 2h pyrimidinehexanoic acid

Journal of Organic Chemistry 56(21): 6007-6018

Alkylation of the tosylates of N-t-Boc-5-(hydroxymethyl)-2-pyrrolidinone and N-t-Boc-6-(hydroxymethyl)-2-piperidinone with the sodium salt of cytosine in dimethyl sulfoxide, followed by acylation of the base excoyclic amine and selective opening of the lactam ring by alkaline hydrolysis, gave the title compounds, respectively, in protected form. Oligomerization was achieved by activation of the carboxyl group as the p-nitrophenyl ester and coupling with the free amine of another subunit in dimethylformamide or dimethyl sulfoxide. A hexamer of the pentanoic acid system could be easily prepared by stepwise coupling of the monomeric units or by block synthesis via trimers. The hexanoic acid derived hexamer could only be prepared by stepwise elongation, mostly due to problems of solubility for this backbone.

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