Development of an isotope-coded activity-based probe for the quantitative profiling of cysteine proteases

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 12, 2004, Pages 3131-3134

  Van Swieten, Paul F ^a   Maehr, Rene ^b   Van Den Nieuwendijk, Adrianus M C H ^a   Kessler, Benedikt M ^b   Reich, Michael ^c   Wong, Chung Sing ^a   Kalbacher, Hubert ^c   Leeuwenburgh, Michiel A ^a   Driessen, Christoph ^c   Van Der Marel, Gijsbert A ^a   Ploegh, Hidde L ^b   Overkleeft, Herman S ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b HARVARD MEDICAL SCHOOL   (United States)

^c UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Active site directed probe; Chemical proteomics; Cysteine proteases; Isotopic labeling; Suicide inhibitor; Synthesis

Indexed keywords

CATHEPSIN; CELL EXTRACT;

ARTICLE; MOLECULAR PROBE; PROTEIN ANALYSIS; PROTEOMICS; QUANTITATIVE ANALYSIS; SYNTHESIS;

CYSTEINE ENDOPEPTIDASES; ISOTOPE LABELING; ISOTOPES; PROTEOMICS;

EID: 2442551640     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.04.046     Document Type: Article

References (23)

1. Henzel W.J., Billeci T.M., Stults J.T., Wong S.C., Grimley C., Watanabe C. Proc. Natl. Acad. Sci. U.S.A. 90:1993;5011
2. Speers A.E., Cravatt B.F. ChemBioChem. 5:2004;41
3. Jeffery D.A., Bogyo M. Curr. Opin. Biotechnol. 14:2003;87
4. Campbell D.A., Szardenings A.K. Curr. Opin. Chem. Biol. 7:2003;296
5. Kozarich J.W. Curr. Opin. Chem. Biol. 7:2003;78
6. Liu Y., Patricelli M.P., Cravatt B.F. Proc. Natl. Acad. Sci. U.S.A. 96:1999;14694
7. Greenbaum D., Medzihradsky K.F., Burlingame A., Bogyo M. Chem. Biol. 7:2000;569
8. Bogyo M., McMaster J.S., Gaczynska M., Tortorella D., Goldberg A.L., Ploegh H.L. Proc. Natl. Acad. Sci. U.S.A. 94:1997;6629
9. Kessler B.M., Tortorella D., Altun M., Kisselev A., Fiebinger E., Hekking B.G., Ploegh H.L., Overkleeft H.S. Chem. Biol. 8:2001;913
10. Lennon-Duménil A.M., Bakker A.H., Maehr R., Fiebiger E., Overkleeft H.S., Rosemblatt M., Ploegh H.L., Lagaudrière-Gesbert C. J. Exp. Med. 196:2002;529
11. Kocks C., Maehr R., Overkleeft H.S., Wang E.W., Iyer L.K., Lennon-Duménil A.M., Ploegh H.L., Kessler B.M. Mol. Cell. Proteomics. 2:2003;1188
12. Gygi S.P., Rist B., Gerber S.A., Turecek F., Gelb M.H., Aebersold R. Nat. Biotechnol. 17:1999;994
13. Recently an efficient synthesis of an ICAT reagent was published: Patel A., Perrin D.M. Bioconjugate Chem. 15:2004;224
14. Tao W.A., Aebersold R. Curr. Opin. Biotechnol. 14:2003;110
15. Gygi S.P., Rist B., Griffin T.J., Eng J., Aebersold R. J. Prot. Res. 1:2002;47
16. Grunidin A.L., Koshika I.M., Domnin I.N. Russ. J. Org. Chem. 29:1993;340
17. Tong G., Lawlor J.M., Tregear G.W., Haralambidis J. J. Org. Chem. 58:1993;2223
18. Bowie J.H., Williams D.H. Tetrahedron. 23:1967;305
19. The reduction of 6-(Fmoc-amino)-hexa-2, 4-diyn-1-ol, 6-(Fmoc-amino)-hexa- 2, 4-diyn-1-tetrahydropyranyl ether and 6-(Fmoc-amino)-hexa-2, 4-diynoic acid methyl ester, prepared via Glaser oxidative couplings of Fmoc-protected propargylamine with propargyl alcohol, 2-(prop-2-yn-1-yloxy)tetrahydro-2H-pyran and methyl propiolate, respectively, under the same conditions resulted in substantial amounts of hexa-, hepta-, and nonadeuterated products
20. Lange M., Undheim K. Tetrahedron. 54:1998;5337
21. Alewood P.F., Benn M., Reinfried R. Can. J. Chem. 52:1974;4083
22. Ovaa H., van Swieten P.F., Kessler B.M., Leeuwenburgh M.A., Fiebiger E., van den Nieuwendijk A.M.C.H., Galardy P.J., van der Marel G.A., Ploegh H.L., Overkleeft H.S. Angew. Chem., Int. Ed. 42:2003;3626
23. Mori K., Iwasawa H. Tetrahedron. 36:1980;87