The 2-(4-trifluoromethylphenylsulfonyl)ethoxycarbonyl (Tsc) amino-protecting group: Use in the solid-phase synthesis of pyrrole-imidazole polyamides

Tetrahedron Letters

Volumn 44, Issue 8, 2003, Pages 1607-1610

  Choi, Jin Seok ^a   Lee, Younjoo ^a   Kim, Eunmyoung ^a   Jeong, Nakcheol ^a   Yu, Hosung ^b   Han, Hogyu ^a  

^a Korea University   (South Korea)

^b HanChem Co Ltd   (South Korea)

Author keywords

Amino acid; Amino protecting group; Distamycin; DNA; Tsc group

Indexed keywords

2 (4 TRIFLUOROMETHYLPHENYLSULFONYL)ETHOXYCARBONYL; CARBONYL DERIVATIVE; IMIDAZOLE DERIVATIVE; POLYAMIDE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DNA BINDING; SOLID; SYNTHESIS;

EID: 0037450391     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00010-8     Document Type: Article

References (24)

1. Choi J.S., Lee H.-S., Lee Y., Jeong N., Kim H.-J., Kim Y.-D., Han H. Tetrahedron Lett. 43:2002;4295-4299.
2. Wurtz N.R., Turner J.M., Baird E.E., Dervan P.B. Org. Lett. 3:2001;1201-1203.
3. Sabirov A.N., Kim Y.-D., Kim H.-J., Samukov V.V. Protein Peptide Lett. 4:1997;307-312.
4. Park J.-I., Lee S.-H., Lee Y.S., Kim H.-J. Bull. Korean Chem. Soc. 20:1999;244-246.
5. Kader A.T., Stirling C.J.M. J. Chem. Soc. 1964;258-266.
6. Tesser G.I., Balvert-Geers I.C. Int. J. Peptide Protein Res. 7:1975;295-305.
7. Verhart C.G.J., Tesser G.I. Recl. Trav. Chim. Pays-Bas. 107:1988;621-626.
8. Samukov V.V., Sabirov A.N., Pozdnyakov P.I. Tetrahedron Lett. 35:1994;7821-7824.
9. Baird E.E., Dervan P.B. J. Am. Chem. Soc. 118:1996;6141-6146.
10. 3) δ 155.05, 152.08, 145.24, 139.89, 129.29, 128.75, 128.32, 128.17, 127.89, 127.45, 125.87, 125.82, 125.77, 125.72, 125.69, 125.15, 122.09, 121.55, 118.48, 66.78, 30.95.
11. +), calcd 444.0453, found 444.0464.
12. 4 versus 0.1N LiOH) than methyl and ethyl esters.
13. Stigers K.D., Koutroulis M.R., Chung D.M., Nowick J.S. J. Org. Chem. 65:2000;3858-3860.
14. Carpino L.A., Wu A.-C. J. Org. Chem. 65:2000;9238-9240.
15. Bodanszky M., Deshmane S.S., Martinez J. J. Org. Chem. 44:1979;1622-1625.
16. 2 were used for comparison experiments and its cleavage was monitored by UV absorption at 254/290 nm.
17. The deprotection rate was slightly faster by addition of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (1% v/v) to a 20% piperidine-DMF solution.
18. -1).
19. Carpino L.A., El-Faham A. J. Am. Chem. Soc. 117:1995;5401-5402.
20. Coste J., Frérot E., Jouin P. Tetrahedron Lett. 32:1991;1967-1970.
21. Boger D.L., Fink B.E., Hedrick M.P. J. Am. Chem. Soc. 122:2000;6382-6394.
22. Krutzik P.O., Chamberlin A.R. Bioorg. Med. Chem. Lett. 12:2002;2129-2132. and references cited therein.
23. +), calcd 1364.6554/1386.6373, found 1365.1753/1387.1616.
24. Kent S.B.H. Annu. Rev. Biochem. 57:1988;957-989.