Postsynthetic modification of peptides via chemoselective N-alkylation of their side chains

Organic Letters

Volumn 14, Issue 7, 2012, Pages 1664-1667

  Monfregola, Luca ^a   Leone, Marilisa ^b   Calce, Enrica ^b   De Luca, Stefania ^b  

^a UNIVERSITY OF COLORADO   (United States)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; DRUG DERIVATIVE; LYSINE; PEPTIDE;

ALKYLATION; AMINO ACID SEQUENCE; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MOLECULAR GENETICS; NUCLEAR MAGNETIC RESONANCE;

ALKYLATION; AMINO ACID SEQUENCE; DISULFIDES; LYSINE; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDES;

EID: 84859621633     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300437w     Document Type: Article

References (18)

1. Jungheim, L. N.; Shepperd, T. A.; Baxter, A. J.; Burguess, J.; Hatch, S. D.; Lubbehusen, P.; Wiskerchen, M.; Muesing, M. A. J. Med. Chem. 1996, 39, 96-108
2. Dal Pozzo, A.; Bergonzi, R.; Minghong, N. Tetrahedron Lett. 2001, 42, 3925-3927
3. Dal Pozzo, A.; Minghong, N.; Muzi, L.; Caporale, A.; De Castiglione, R.; Kaptein, B.; Broxterman, Q. B.; Formaggio, F. J. Org. Chem. 2002, 67, 6372-6375
4. Minghong, N.; Esposito, E.; Kaptein, B.; Broxterman, Q. B.; Dal Pozzo, A. Tetrahedron Lett. 2005, 46, 6369-6371
5. Ooi, T.; Tayama, E.; Maruoka, K. Angew. Chem., Int. Ed. 2003, 42, 579-582
6. Espuna, G.; Arsequell, G.; Valencia, G.; Barluenga, J.; Alvarez-Gutiérrez, J. M.; Ballesteros, A.; Gonzales, J. M. Angew. Chem., Int. Ed. 2004, 43, 325-329
7. Ruiz-Rodriguez, J.; Albericio, F.; Lavilla, R. Chem.-Eur. J. 2010, 16, 1124-1127
8. Tedaldi, L. M.; Smith, M. E. B.; Nathani, R. I.; Baker, J. R. Chem. Commun. 2009, 43, 6583-6585
9. Huang, R.; Holbert, M. A.; Tarrant, M. K.; Curtet, S.; Colquhoun, D. R.; Dancy, B. M.; Dancy, B. C.; Hwang, Y.; Tang, Y.; Meeth, K.; Marmorstein, R.; Cole, R. N.; Khochbin, S.; Cole, P. A. J. Am. Chem. Soc. 2010, 132, 9986-9987
10. Carrasco, M. R.; Silva, O.; Rawls, K. A.; Sweeney, M. S.; Lombardo, A. A. Org. Lett. 2006, 8, 3529-3532
11. Chan, A. O.-Y.; Ho, C.-M.; Chong, H.-C.; Leung, Y.-C.; Huang, J.-S.; Wong, M.-K.; Che, C.-M. J. Am. Chem. Soc. 2012, 134, 2589-2598
12. Demmer, O.; Dijkgraaf, I.; Schottelius, M.; Wester, H.-J.; Kessler, H. Org. Lett. 2008, 10, 2015-2018
13. Monfregola, L.; De Luca, S. Amino Acids 2011, 41, 981-990
14. De Luca, S.; Della Moglie, R.; De Capua, A.; Morelli, G. Tetrahedron Lett. 2005, 46, 6637-6640
15. Hasegawa, M.; Ono, F.; Kanemasa, S. Tetrahedron Lett. 2008, 49, 5220-5223
16. De Luca, S.; Ulhaq, S.; Dixon, M. J.; Essex, J.; Bradley, M. Tetrahedron Lett. 2003, 44, 3195-3197
17. Kiso, Y.; Satomi, M.; Ukawa, K.; Akita, T. J. Chem. Soc., Chem. Commun. 1980, 22, 1063-1064
18. Chan, W. C.; White, P. D. Fmoc solid phase peptide synthesis. A practical approach; Oxford University Press: USA, 2000.