Solid-phase synthesis of peptide thioacids through hydrothiolysis of resin-bound peptide thioesters

Tetrahedron Letters

Volumn 49, Issue 42, 2008, Pages 6122-6125

  Zhang, Xiaohong ^a   Lu, Xiao Wei ^a   Liu, Chuan Fa ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; MACROGOL; PEPTIDE DERIVATIVE; RESIN; THIOACID; THIOESTER;

AMINO TERMINAL SEQUENCE; ARTICLE; CHEMICAL BINDING; CHEMICAL BOND; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; HYDROTHIOLYSIS; PEPTIDE SYNTHESIS;

EID: 50549098156     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.08.018     Document Type: Article

References (22)

1. Merrifield R.B. J. Am. Chem. Soc. 85 (1963) 2149-2154
2. Marshall G.R. J. Pept. Sci. 9 (2003) 534-544
3. Caruthers M.H. Science 230 (1985) 281-285
4. Früchtel J.S., and Jung G. Angew. Chem., Int. Ed. 35 (1996) 17-42
5. Lam K.S., Salmon S.E., Hersh E.M., Hruby V.J., Kazmierski W.M., and Knapp R.J. Nature 353 (1991) 82-84
6. Houghten R.A. Proc. Natl. Acad. Sci. U.S.A. 82 (1985) 5131-5135
7. Thompson L.A., and Ellman J.A. Chem. Rev. 96 (1996) 555-600
8. Tan X.-H., Zhang X., Yang R., and Liu C.-F. ChemBioChem 9 (2008) 1052-1056
9. Liu C.F., Rao C., and Tam J.P. Tetrahedron Lett. 37 (1996) 933-936
10. Shangguan N., Katukojvala S., Greenberg R., and Williams L.J. J. Am. Chem. Soc. 125 (2003) 7754-7755
11. Merkx R., Brouwer A.J., Rijkers D.T.S., and Liskamp R.M.J. Org. Lett. 7 (2005) 1125-1128
12. Blake J. Int. J. Pept. Protein Res. 17 (1981) 273-274
13. Gaertner H., Villain M., Botti P., and Canne L. Tetrahedron Lett. 45 (2004) 2239-2241
14. Goldstein A.S., and Gelb M.H. Tetrahedron Lett. 41 (2000) 2797-2800
15. Cote, S. PCT Int. Appl. 2005, WO 2005012277 AI 20050210 CAN 142: 198979 AN 2005: 120909.
16. Camperi S.A., Marani M.M., Iannucci N.B., Cote S., Albericio F., and Cascone O. Tetrahedron Lett. 46 (2005) 1561-1564
17. Garcia-Martin F., Quintanar-Audelo M., Garcia-Ramos Y., Cruz L.J., Gravel C., Furic R., Cote S., Tulla-Puche J., and Albericio F. J. Comb. Chem. 8 (2006) 213-220
18. Li X., Kawakami T., and Aimoto S. Tetrahedron Lett. 39 (1998) 8669-8672
19. 2O with ice cooling. The mixture was subjected to HPLC purification to give the purified thioacid peptide. All operations should be performed in a well-ventilated fume hood.
20. Kolakowski R.V., Shangguan N., Sauers R.R., and Williams L.J. J. Am. Chem. Soc. 128 (2006) 5695-5702
21. HPLC purified peptide thioacid (ca. 0.25 mM) was mixed with tosyl azide (ca. 2 mM) and 2,6-lutidine (ca. 2 mM) in wet methanol, and the reaction mixture was monitored by analytical HPLC.
22. 2O (0.05% TFA, pH 2). A yellow color developed immediately. The pH of the reaction solution was then adjusted to about 6 with 0.2 M phosphate buffer. TCEP was added after 10 min for thiolytic reduction, and the reaction mixture was subjected to HPLC purification.