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The Prooligonucleotide Approach: Synthesis of Mixed Phosphodiester and SATE Phosphotriester Prooligonucleotides Using H ‐Phosphonate and Phosphoramidite Chemistries
Author(s) -
Bologna JeanCharles,
Morvan François,
Imbach JeanLouis
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199909)1999:9<2353::aid-ejoc2353>3.0.co;2-z
Subject(s) - phosphonate , chemistry , phosphoramidite , phosphodiester bond , yield (engineering) , stereochemistry , combinatorial chemistry , organic chemistry , oligonucleotide , biochemistry , rna , dna , materials science , metallurgy , gene
Abstract The synthesis of mixed SATE‐phosphotriester and phosphodiester prooligonucleotides using both phosphoramidite and H ‐phosphonate chemistries is described. The key step is the selective oxidation of phosphite triester and H ‐phosphonate linkages to yield thiono‐ or oxo‐triester SATE and thiono‐ or oxo‐diester linkages. This approach allows the synthesis of any desired mixed prooligos bearing either t Bu‐ or Me‐SATE enzymolabile protecting groups.