Sensitive Oligodeoxynucleotide Synthesis Using Dim and Dmoc as Protecting Groups
| Autor: | Shiyue Fang, Shahien Shahsavari, Yipeng Yin, Dhananjani N. A. M. Eriyagama, Jinsen Chen, Komal Chillar, Bhaskar Halami |
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| Rok vydání: | 2019 |
| Předmět: |
Base Sequence
010405 organic chemistry Stereochemistry Chemistry Organic Chemistry hemic and immune systems Chemistry Techniques Synthetic respiratory system 010402 general chemistry Phosphate Amides 01 natural sciences Article 0104 chemical sciences chemistry.chemical_compound Oligodeoxyribonucleotides Group (periodic table) Phosphoric Acids |
| Zdroj: | J Org Chem |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | In traditional oligodeoxynucleotide (ODN) synthesis, phosphate groups are protected with the 2-cyanoethyl group, and amino groups are protected with acyl groups. At the end of ODN synthesis, deprotection is achieved with strong bases and nucleophiles. Therefore, traditional technologies are not suitable for the synthesis of ODNs containing sensitive functionalities. To address the problem, we report the use of Dim and Dmoc groups, which are based on the 1,3-dithian-2-yl-methyl function, for phosphate and amine protection for the solid phase ODN synthesis. Using the new Dim-Dmoc protection, deprotection was achieved under mild oxidative conditions without using any strong bases and nucleophiles. As a result, the new technology is suitable for the synthesis of ODNs containing sensitive functions. To demonstrate feasibility, seven 20-mer ODNs including four that contain sensitive ester and alkyl chloride groups were synthesized, purified with RP HPLC, and characterized with MALDI-TOF MS and enzyme digestion essays. High purity ODNs were obtained. |
| Databáze: | OpenAIRE |
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