Nucleotides, Part LXVII , The 2-Cyanoethyl and (2-Cyanoethoxy)carbonyl Group for Base Protection in Nucleoside and Nucleotide Chemistry
✍ Scribed by Claudia Merk; Tilman Reiner; Evgeny Kvasyuk; Wolfgang Pfleiderer
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- German
- Weight
- 246 KB
- Volume
- 83
- Category
- Article
- ISSN
- 0018-019X
No coin nor oath required. For personal study only.
✦ Synopsis
The amino functions of the common 2'-deoxyribo-and ribonucleosides were blocked by the (2cyanoethoxy)carbonyl group on treatment with 2-cyanoethyl carbonochloridate (5) or 1-[(2-cyanoethoxy)carbonyl]-3-methyl-1H-imidazolium chloride (6) leading to 7, 18, 8, 19, 9, and 20. In 2'-deoxyguanosine, the amide group was additionally blocked at the O 6 position by the 2-cyanoethyl ( 3 27) and 2-(4-nitrophenyl)ethyl group ( 3 31, 32). Comparative kinetic studies regarding the cleavage of the ce/ceoc and npe/npeoc group by b-elimination revealed valuable information about the ease and sequential deprotection of the various blocking groups at different sites of the nucleobases. Besides the 5'
guanosine analog 40 is recommended as building block for oligo-2'-deoxyribonucleotide synthesis.