Sequential peptide ligation by using a controlled cysteinyl prolyl ester (CPE) autoactivating unit

Tetrahedron Letters

Volumn 48, Issue 11, 2007, Pages 1903-1905

  Kawakami, Toru ^a   Aimoto, Saburo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Controlled sequential ligation; CPE autoactivating unit; Peptide ligation; Peptide thioester

Indexed keywords

CYSTEINYLPROLINE ESTER; PEPTIDE; UNCLASSIFIED DRUG;

ACYLATION; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; MOLECULAR STABILITY; NONPHOTOCHEMICAL QUENCHING; PEPTIDE SYNTHESIS; PROTEIN GLYCOSYLATION; PROTEIN METHYLATION; PROTEIN PHOSPHORYLATION; PROTEIN STRUCTURE; SEQUENTIAL ANALYSIS; STRUCTURE ANALYSIS;

EID: 33846923785     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.01.086     Document Type: Article

References (23)

1. Dawson P.E., and Kent S.B.H. Annu. Rev. Biochem. 69 (2000) 923-960
2. Aimoto S. Curr. Org. Chem. 5 (2001) 45-87
3. Muir T.W. Annu. Rev. Biochem. 72 (2003) 249-289
4. Hojo H., and Aimoto S. Bull. Chem. Soc. Jpn. 64 (1991) 111-117
5. Kawakami T., Kogure S., and Aimoto S. Bull. Chem. Soc. Jpn. 69 (1996) 3331-3338
6. Dawson P.E., Muir T.W., Clark-Lewis I., and Kent S.B.H. Science 266 (1994) 776-779
7. Tam J.P., Lu C.-F., and Shao J. Proc. Natl. Acad. Sci. U.S.A. 92 (1995) 12485-12489
8. Canne L.E., Bark S.J., and Kent S.B.H. J. Am. Chem. Soc. 118 (1996) 5891-5896
9. Botti P., Carrasco M.R., and Kent S.B.H. Tetrahedron Lett. 42 (2001) 1831-1833
10. Kawakami T., Akaji K., and Aimoto S. Org. Lett. 3 (2001) 1403-1405
11. Offer J., Boddy C.N.C., and Dawson P.E. J. Am. Chem. Soc. 124 (2002) 4642-4646
12. Kawakami T., and Aimoto S. Tetrahedron Lett. 44 (2003) 6059-6061
13. Marinzi C., Offer J., Longhi R., and Dawson P.E. Bioorg. Med. Chem. 12 (2004) 2749-2757
14. Kawakami T., and Aimoto S. Chem. Lett. 36 (2007) 76-77
15. Kawakami T., Sumida M., Nakamura K., Vorherr T., and Aimoto S. Tetrahedron Lett. 46 (2005) 8805-8807
16. Nakamura K., Sumida M., Kawakami T., Vorherr T., and Aimoto S. Bull. Chem. Soc. Jpn. 79 (2006) 1773-1780
17. Zanotti G., Pinnen F., and Lucente G. Tetrahedron Lett. 26 (1985) 5464-5481
18. 0.91.
19. 0.92.
20. In the native chemical ligation reaction, an additional aryl thiol, such as thiophenol, is usually used to enhance the reactivity of the thioester by in situ transthioesterification, and several thiols were examined;. Johnson E.C.B., and Kent S.B.H. J. Am. Chem. Soc. 128 (2006) 6640-6646
21. 3b
22. 2, with peptide 7 was increased from 60% to 65% or from 49% to 68%, respectively. In these ligation reactions, only a small amount of THP was added, and acetonitrile was added to dissolve peptides. Other additives, such as thiols and Gdn, could also be useful. The ligation reactions proceeded faster in a buffer solution at the pH over 8 than at that below 8.
23. Bang D., Pentelute B.L., and Kent S.B.H. Angew. Chem., Int. Ed. 45 (2006) 3985-3988