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Phosphorylating agent for the synthesis of oligonucleotide with aliphatic amino group at 5′ end

✍ Scribed by Toshiki Tanaka; Shigeru Tamatsukuri; Morio Ikehara

Book ID
104227628
Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
264 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

A lipophilic phosphorylating agent was prepared and used for the synthesis of pentadeoxyribonucleotide with aminoethyl group at 5' end on a polymer support by the phosphotriester method. Chemically synthesized oligodeoxyribonucleotide with defined sequence is widely used as the primer for DNA sequence determination procedure 1 . Such oligonucleotide which has hydroxyl group at 5' end is first labeled by means of [v-32 P]ATP and polynucleotide kinase. However, since this method requires the use of radioisotopes, other alternative means of detection procedure were investigated. Recently the fluorescent compounds such as fluorescein, tetramethylrhodamine, Texas Red and 7-nitrobenzo-2-oxa-1-diazole were applied for this purpose and successfully used2. This strategy is very attractive since the primer is non-radioactive and safe. As the fluorescent compounds were attached to the primary amino group of oligonucleotide, the synthesis of oligonucleotide with primary amino group at 5' end was necessary. Smith and co-workers2a prepared 5' -amino-5'-deoxythymidine and converted it to its phosphoramidite derivative. However this procedure needs the four types of 5'-amino-S'-deoxynucleotides. Coull and co-workers3 and Agrawal and coworkers 4 prepared phosphitylating reagent for the synthesis of oligonucleo-

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