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Nucleotides, Part LXII , Pyridinium Salts – An Effective Class of Catalysts for Oligonucleotide Synthesis

✍ Scribed by Markus Beier; Wolfgang Pfleiderer

Publisher
John Wiley and Sons
Year
1999
Tongue
German
Weight
158 KB
Volume
82
Category
Article
ISSN
0018-019X

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✦ Synopsis

Various pyridinium salts (see 1 ± 9) have been tested as catalysts for the condensation step in the phosphoramidite approach of oligonucleotide synthesis. Pyridinium chloride (1) turned out to be the most effective activator, speeding up the condensation tremendously. Pyridinium bromide (2) and 4-methylbenzenesulfonate (4) can also be regarded as powerful substitutes for the commonly used 1H-tetrazole. The acidic pK a of the pyridinium cation provides an optimal range for phosphoramidite activation, which is followed by a nucleophilic attack of the pyridine ring to give the P-pyridinio intermediate 11 as the most likely precursor of phosphite ester formation (Scheme). 31 P-NMR Studies support this proposal indirectly.

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