Characterization of synthetic peptide byproducts from cyclization reactions using on-line HPLC-ion spray and tandem mass spectrometry

Letters in Peptide Science

Volumn 3, Issue 6, 1997, Pages 357-370

  Arttamangkul, Seksiri ^a,c   Arbogast, Brian ^a   Barofsky, Douglas ^a   Aldrich, Jane V ^b  

^a OREGON STATE UNIVERSITY   (United States)

^b UNIVERSITY OF MARYLAND SCHOOL OF PHARMACY   (United States)

^c MOLECULAR PROBES INC   (United States)

Author keywords

Aspartimide rearrangement; BOP; Dipyrrolidinylguanidinium; Dynorphin A derivative; HAPyU; HATU; Tetramethylguanidinium

Indexed keywords

EID: 0001013369     PISSN: 09295666     EISSN: None     Source Type: Journal    
DOI: 10.1007/bf00127967     Document Type: Article

References (23)

1. Kim, H.Y., Pilosof, D., Dyckes, D.F. and Vestal, M.L., J. Am. Chem. Soc., 106 (1984) 7304.
2. Krishnamurthy, T., Szafraniec, L., Hunt, D.F., Shabanowitz, J., Yates III, J.R., Hauer, C.R., Carmichael, W.W., Skulberg, O., Codd, G.A. and Missler, S., Proc. Natl. Acad. Sci. USA, 86 (1989) 770.
3. Biemann, K. and Scoble, H., Science, 237 (1987) 992.
4. Tseng, J.-L., Yan, L., Fridland, G.H. and Desiderio, D.M., Rapid Commun. Mass Spectrom., 9 (1995) 264.
5. Metzger, J.W., Wiesmüller, K.-H., Gnau, V., Brünjes, J. and Jung, G., Angew. Chem. Int. Ed. Engl., 32 (1993) 894.
6. Beck-Sickinger, A.G., Schnorrenberg, G., Metzger, J. and Jung, G., Int. J. Pept. Protein Res., 38 (1991) 25.
7. Papayannopoulos, I.A. and Biemann, K., Pept. Res., 5 (1992) 83.
8. Johnson, R.S., Martin, S.A., Biemann, K., Stults, J.T. and Watson, J.T., Anal. Chem., 59 (1987) 2621.
9. Lloyd, J.R., Cotter, M.L., Ohori, D. and Doyle, D.L., Biomed. Environ. Mass Spectrom., 15 (1988) 399.
10. Arttamangkul, S., Murray, T.F., DeLander, G.E. and Aldrich, J.V., J. Med. Chem., 38 (1995) 2410.
11. Arttamangkul, S., Leelasvatanakij, L. and Aldrich, J.V., manuscript in preparation.
12. Castro, B., Dormoy, J.-R., Evin, G. and Selve, C., Tetrahedron Lett., 14 (1975) 1219.
13. Carpino, L.A., J. Am. Chem. Soc., 115 (1993) 4397.
14. Mann, M., Meng, C.K. and Fenn, J.B., Mass Spectrom., 61 (1989) 1702.
15. Biemann, K., Biomed. Environ. Mass Spectrom., 16 (1988) 99.
16. Stewart, J.M. and Young, J.D., Solid Phase Peptide Synthesis, 2nd ed., Pierce Chemical Co., Rockford, IL, U.S.A., 1984, pp. 42-43.
17. Nicolas, E., Pedroso, E. and Giralt, E., Tetrahedron Lett., 30 (1989) 947.
18. Gausepohl, H., Pieles, U. and Frank, R.W., In Smith, J.A. and Rivier, J.E. (Eds.) Peptides: Chemistry and Biology (Proceedings of the 12th American Peptide Symposium), ESCOM, Leiden, The Netherlands, 1992, pp. 523-524.
19. Abdelmoty, I., Albericio, F., Carpino, L.A., Foxman, B.M. and Kates, S.A., Lett. Pept. Sci., 1 (1994) 57.
20. Roepstorff, P. and Fohlman, J., Biomed. Mass Spectrom., 11 (1984) 601.
21. Biemann, K., Methods Enzymol., 193 (1990) 886.
22. Johnson, R.S., Ph.D. Thesis, Massachusetts Institute of Technology, Cambridge, MA, U.S.A., 1988.
23. Johnson, R.S., Martin, S.A., Biemann, K., Stults, J.T. and Watson, J.T., Anal. Chem., 57 (1987) 2621.