Bis(hydroxymethyl)phosphinic acid analogues of acyclic nucleosides; synthesis and incorporation into short DNA oligomers

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Abstract

Novel analogues of acyclic nucleosides based on a bis(hydroxymethyl)phosphinic acid (BHPA) backbone were obtained by condensation of the bis(4,4′-dimethoxytrityl) derivative of BHPA with N-1- or N-3-(2-hydroxyethyl)thymine in the presence of MSNT, or by an Appel reaction with N-1- or N-3-(2-aminoethyl)thymine. After selective deprotection and phosphitylation they were used as monomers for automated solid support synthesis of short oligomers by the phosphoramidite approach. © 2002 Elsevier Science Ltd. All rights reserved.

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Nawrot, B., Michalak, O., Nowak, M., Okruszek, A., Dera, M., & Stec, W. J. (2002). Bis(hydroxymethyl)phosphinic acid analogues of acyclic nucleosides; synthesis and incorporation into short DNA oligomers. Tetrahedron Letters, 43(31), 5397–5400. https://doi.org/10.1016/S0040-4039(02)01067-5

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