Orthogonal coupling of unprotected peptide segments through histidyl amino terminus

Tetrahedron Letters

Volumn 38, Issue 1, 1997, Pages 3-6

  Zhang, Lianshan ^a   Tam, James P ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; PEPTIDE SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0031013619     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02260-5     Document Type: Article

References (11)

1. Tam, J.P.; Lu, Y.-A.; Liu, C.F.; Shao, J. Proc. Natl. Acad. Sci. USA 1995, 92, 12485-12489.
2. (a) Kemp D.S.; Corey, R.I.; Dewan, J.C.; Galakatos, N.G.; Kerkman, D.; Leung, S.-L. J. Org. Chem. 1989, 54, 1589-1603.
3. (b) Kemp D.S.; Corey, R.I. Tetrahedron Lett. 1991, 32, 2845-2848.
4. (c) Brenner, M.; Zimmermann, J.P.; Wehrmüller, J.; Quitt, P.; Hartmann, A.; Schneider, W.; Beglinger, U. Helv.Chim. Acta 1957, 40, 1497-1517
5. Liu, C.F.; Tam, J.P. J. Am. Chem. Soc. 1994, 116, 4149-4153.
6. (b) Liu, C.F.; Tam, J.P. Proc. Natl. Acad. Sci. USA 1994, 91, 6584-6588.
7. Dawson, P.E.; Muir, T.W.; Clark-Lewis, I.; Kent, S.B.H. Science 1994, 266, 776-779.
8. Liu, C.F.; Rao, C.; Tam, J.P. Tetrahedron Lett. 1996, 37, 933-936.
9. Wieland, T.; Bokelmann, E.; Bauer, L.; Lang, H.U.; Lau, H. Liebigs Ann. Chem. 1953, 583, 129-149.
10. Typically, 0.01 mmol model peptide, His-Gly-Lys-Ala and 0.01-0.02 mmol Ellman's reagent were dissolved in l ml of 0.2 N phosphate buffer (pH 5.7) and added to 0.01 mmol thiocarboxylic acid. After 8 hr, the reaction was monitored by RP-HPLC, the individual peak identified by MALDI-MS and compared with the authentic standard.
11. Yamashiro, D.; Li, C.H. Int. J. Pept. Protein Res. 1988, 31, 322-334.