Fragment condensation of C-terminal pseudoproline peptides without racemization on the solid phase

Angewandte Chemie - International Edition

Volumn 50, Issue 28, 2011, Pages 6406-6410

  Heinlein, Christian ^a   Varón Silva, Daniel ^a   Tröster, Andrea ^a   Schmidt, Jasmin ^a   Gross, Angelina ^a   Unverzagt, Carlo ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

fragment coupling; glycopeptides; peptide synthesis; ribonucleases; solid phase synthesis

Indexed keywords

FRAGMENT COUPLING; GLYCOPEPTIDES; PEPTIDE SYNTHESIS; RIBONUCLEASES; SOLID PHASE SYNTHESIS;

COUPLINGS;

PEPTIDES;

DRUG DERIVATIVE; PEPTIDE; PROLINE; PSEUDOPROLINE; RIBONUCLEASE; THIAZOLE DERIVATIVE;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; MICROWAVE RADIATION; MOLECULAR GENETICS; STEREOISOMERISM; SYNTHESIS;

AMINO ACID SEQUENCE; MICROWAVES; MOLECULAR SEQUENCE DATA; PEPTIDES; PROLINE; RIBONUCLEASES; STEREOISOMERISM; THIAZOLES;

EID: 79959865281     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201101270     Document Type: Article

References (28)

1. C. P. Hackenberger, D. Schwarzer, Angew. Chem. 2008, 120, 10182
2. Angew. Chem. Int. Ed. 2008, 47, 10030.
3. P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. Kent, Science 1994, 266, 776
4. H. Hojo, S. Aimoto, Bull. Chem. Soc. Jpn. 1991, 64, 111.
5. T. Haack, M. Mutter, Tetrahedron Lett. 1992, 33, 1589.
6. C. Piontek, D. Varón Silva, C. Heinlein, C. Pöhner, S. Mezzato, P. Ring, A. Martin, F. X. Schmid, C. Unverzagt, Angew. Chem. 2009, 121, 1974
7. Angew. Chem. Int. Ed. 2009, 48, 1941.
8. Y. Kajihara, A. Yoshihara, K. Hirano, N. Yamamoto, Carbohydr. Res. 2006, 341, 1333.
9. P. Lloyd-Williams, F. Albericio, E. Giralt, Tetrahedron 1993, 49, 11065.
10. A. R. Katritzky, M. Yoshioka, T. Narindoshvili, A. Chung, N. M. Khashab, Chem. Biol. Drug Des. 2008, 72, 182.
11. T. Yoshiya, Y. Sohma, F. Fukao, A. Taniguchi, S. Nakamura, M. Skwarczynski, T. Kimura, Y. Hayashi, Y. Kiso, Pept. Sci. 2006, 43, 43.
12. T. Wöhr, F. Wahl, A. Nefzi, B. Rohwedder, T. Sato, X. Sun, M. Mutter, J. Am. Chem. Soc. 1996, 118, 9218.
13. Novabiochem in Innovations, Vol. 6/04, 2004, http://www.emdbiosciences. com/html/NBC/innovations.htm
14. I. Coin, P. Schmieder, M. Bienert, M. Beyermann, J. Pept. Sci. 2008, 14, 299
15. Genzyme in http://www.genzymepharmaceuticals.com/pdf/Genzyme- Pseudoproline-dipeptide-flyer.pdf, 2010.
16. A. Nefzi, K. Schenk, M. Mutter, Protein Pept. Lett. 1994, 1, 66
17. P. Dumy, M. Keller, D. E. Ryan, B. Rohwedder, T. Woehr, M. Mutter, J. Am. Chem. Soc. 1997, 119, 918.
18. K. Barlos, D. Gatos, W. Schaefer, Angew. Chem. 1991, 103, 572
19. Angew. Chem. Int. Ed. Engl. 1991, 30, 590.
20. X. Li, T. Kawakami, S. Aimoto, Tetrahedron Lett. 1998, 39, 8669.
21. A. B. Clippingdale, C. J. Barrow, J. D. Wade, J. Pept. Sci. 2000, 6, 225.
22. M. Quibell, L. C. Packman, T. Johnson, J. Am. Chem. Soc. 1995, 117, 11656
23. C. Zikos, E. Livaniou, L. Leondiadis, N. Ferderigos, D. S. Ithakissios, G. P. Evangelatos, J. Pept. Sci. 2003, 9, 419.
24. E. Bardaji, J. L. Torres, P. Clapes, F. Albericio, G. Barany, R. E. Rodriguez, M. P. Sacristan, G. Valencia, J. Chem. Soc. Perkin Trans. 1 1991, 1755.
25. H. M. Yu, S. T. Chen, K. T. Wang, J. Org. Chem. 1992, 57, 4781.
26. R. Ingenito, E. Bianchi, D. Fattori, A. Pessi, J. Am. Chem. Soc. 1999, 121, 11369.
27. N. L. Benoiton, Y. C. Lee, R. Steinaur, F. M. Chen, Int. J. Pept. Protein Res. 1992, 40, 559.
28. S. Flemer, Jr., J. Pept. Sci. 2009, 15, 693.