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Use of Allylic Protecting Groups for the Synthesis of Base‐Sensitive Prooligonucleotides
Author(s) -
Spinelli Nicolas,
Meyer Albert,
Hayakawa Yoshihiro,
Imbach JeanLouis,
Vasseur JeanJacques
Publication year - 2002
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 - 10.1002/1099-0690(20021)2002:1<49::aid-ejoc49>3.0.co;2-7
Subject(s) - chemistry , phosphodiester bond , phosphoramidite , allylic rearrangement , nucleobase , combinatorial chemistry , palladium , base (topology) , stereochemistry , organic chemistry , catalysis , dna , oligonucleotide , rna , biochemistry , gene , mathematical analysis , mathematics
The synthesis of mixed MeSATE‐phosphotriester and ‐phosphodiester prooligonucleotides [MeSATE = 2‐(acetylthio)ethyl] of various sequences is described. The strategy is based on the use of allyloxycarbonyl (AOC) protection for nucleobases and MeSATE and allyl (All) protection for internucleosidic phosphates, in combination with palladium(0) deprotection. The synthesis was achieved by the use of phosphoramidite chemistry on a photolabile solid support, enabling MALDI‐TOF mass spectrometric analysis to be performed on the still anchored prooligonucleotides