Improved phosphoramidite building blocks for the synthesis of the simplified nucleic acid GNA

Journal of Organic Chemistry

Volumn 74, Issue 12, 2009, Pages 4615-4618

  Schlegel, Mark K ^a   Meggers, Eric ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO GROUP; BUILDING BLOCK; CHEMICAL EQUATIONS; DEPROTECTION; HIGHER YIELD; PHOSPHORAMIDITE; PHOSPHORAMIDITES; RAPID SYNTHESIS; SOLID PHASE SYNTHESIS;

AMINATION; AMINES; ETHYLENE GLYCOL; NUCLEIC ACIDS; OLIGONUCLEOTIDES;

SYNTHESIS (CHEMICAL);

ACETAMIDE; ADENINE; CYTOSINE; FORMAMIDINE; GLYCOL; GUANINE; NUCLEIC ACID; OLIGONUCLEOTIDE; PHOSPHORAMIDOUS ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; DEPROTECTION REACTION; SOLID PHASE SYNTHESIS;

ADENINE; FORMAMIDES; GLYCOLS; GUANINE; NUCLEIC ACIDS; OLIGONUCLEOTIDES; ORGANOPHOSPHORUS COMPOUNDS;

EID: 67249104239     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900365a     Document Type: Article

References (16)

1. Zhang, L.; Peritz, A.; Meggers, E. J. Am. Chem. Soc. 2005, 127, 4174-4175.
2. Schlegel, M. K.; Peritz, A. E.; Kittigowittana, K.; Zhang, L.; Meggers, E. ChemBioChem 2007, 8, 927-932.
3. Schlegel, M. K.; Essen, L.-O.; Meggers, E. J. Am. Chem. Soc. 2008, 130, 8158-8159.
4. Schlegel, M. K.; Xie, X.; Zhang, L.; Meggers, E. Angew. Chem., Int. Ed. 2009, 48, 960-963.
5. Zhang, R. S.; McCullum, E. O.; Chaput, J. C. J. Am. Chem. Soc. 2008, 130, 5846-5847.
6. Schaller, H.; Weimann, G.; Lerch, B.; Khorana, H. G. J. Am. Chem. Soc. 1963, 85, 3821-3827.
7. Ti, G. S.; Gaffney, B. L.; Jones, R. A. J. Am. Chem. Soc. 1982, 104, 1316-1319.
8. Zhang, L.; Peritz, A. E.; Carroll, P. J.; Meggers, E. Synthesis 2006, 645-653.
9. McBride, L. J.; Kierzek, R.; Beaucage, S. L.; Caruthers, M. H. J. Am. Chem. Soc. 1986, 108, 2040-2048.
10. Vu, H.; McCollum, C.; Jacobsen, K.; Theisen, P.; Vinayak, R.; Spiess, E.; Andrus, A. Tetrahedron Lett. 1990, 31, 7269-7272.
11. Vinayak, R.; Anderson, P.; McCollum, C.; Hampel, A. Nucleic Acids Res. 1992, 20, 1265-1269.
12. 2-isobutyryl amide protection group of the guanosine nucleoside takes approximately 10 h in aqueous ammonia at 55°C to be removed. See, for example: (a) Koster, H.; Kulikowski, K.; Liese, T.; Heikens, W.; Kohli, V. Tetrahedron 1981, 37, 363-369.
13. (b) Schulhof, J. C.; Molko, D.; Teoule, R. Nucleic Acids Res. 1987, 15, 397-416.
14. Lembicz, N. K.; Grant, S.; Clegg, W.; Griffin, R. J.; Heath, S. L.; Golding, B. T. J. Chem. Soc., Perkin Trans. 1 1997, 185-186.
15. Rosenbohm, C.; Christensen, S. M.; Sørensen, M. D.; Pedersen, D. S.; Larsen, L.-E.; Wengel, J.; Koch, T. Org. Biomol. Chem. 2003, 1, 655-663.
16. Reddy, M. P.; Hanna, N. B.; Farooqui, F. Tetrahedron Lett. 1994, 35, 4311-4314.