Abstract

YANEZ, Jorge; SOBERON, Xavier  and  GAYTAN, Paul. Rutas alternas de síntesis para la preparación de Fmoc-Trinucleósido-Difosfato Fosforamiditos. Rev. Soc. Quím. Méx [online]. 2004, vol.48, n.1, pp.26-37. ISSN 0583-7693.

Fmoc-trinucleoside-diphosphate phosphoramidites are molecules assembled with three nucleosides, having application as mutagenic units during automated synthesis of oligonucleotides. These synthons afford substitution of wild-type codons by complete mutant codons in a specific region of the target gene, avoiding at the protein level, the bias toward certain kind of amino acids that is generated with conventional methods of mutagenesis. In the present work, three pathways of organic synthesis were explored for the preparation of such valuable compounds, setting as main goal the achievement of clean, one-pot internucleotidic reactions that enable the easy purification of the target compound by column chromatography. Syntheses were performed in liquid-phase and gram-scales through the phosphotriester method. The best pathway for the preparation of dinucleotides and trinucleotides made use of 2-chlorophenyl-O,O-bis(1-hydroxybenzotriazoly)phosphate as phosphorylating reagent.

Keywords : Oligonucleotides; trinucleotide-phosphoramidites; muta-genesis; enzymes; codon; Fmoc.

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