[61] Chemical synthesis of deoxyoligonucleotides by the modified triester method

作者: S.A. Narang , R. Brousseau , H.M. Hsiung , J.J. Michniewicz

DOI: 10.1016/S0076-6879(80)65063-0

关键词: Sequence (biology)Column chromatographyOrganic chemistryOligonucleotidePyrophosphateChemical synthesisProtecting groupMoleculePhosphodiester bondChemistry

摘要: Publisher Summary This chapter discusses the techniques for chemical synthesis of deoxyoligonucleotides by modified triester method. The basic principle method is to mask each internucleotidic phosphodiester function a suitable protecting group during course building sequence. As uncharged molecules, phosphotriester intermediates are soluble in organic solvents and amenable such conventional purification chemistry as silica-gel column chromatography. After desired sequence, all groups can be removed at final step give deoxyoligonucleotide containing natural 3'→ 5'-phosphodiester bonds. main advantages this (1) opportunity large-scale synthesis, (2) short time periods steps, (3) high yields using stoichiometric amounts reactants. due absence any endo-P-O' oligonucleotide chain thus avoiding scission pyrophosphate formation. intermediate so synthesized always contained masked 3'-phosphate group, original necessity phosphorylation condensation stage was eliminated, simplifying approach.

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