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Volumn 5, Issue 5, 2003, Pages 609-612

Diazotrifluoropropionamido-containing prenylcysteines: Syntheses and applications for studying isoprenoid-protein interactions

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE DERIVATIVE; ISOPRENOID; PROPIONAMIDE DERIVATIVE; PROTEIN; RHODIUM DERIVATIVE; AMIDE; BENZOPHENONE; BENZOPHENONE DERIVATIVE; BIOTIN; CROSS LINKING REAGENT; CYSTEINE; DIAZONIUM COMPOUND; DIAZOTRIFLUOROPROPIONAMIDE; DRUG DERIVATIVE; GUANINE NUCLEOTIDE DISSOCIATION INHIBITOR; RHO GUANINE NUCLEOTIDE DISSOCIATION INHIBITORS; STREPTAVIDIN;

EID: 0037866872     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026752a     Document Type: Article
Times cited : (20)

References (38)
  • 3
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    • (1993) Science , vol.259 , pp. 1865-1866
    • Marshall, C.J.1
  • 12
    • 0141440544 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Minnesota, Minneapolis, Minnesota
    • Edelstein, R. L. Ph.D. Thesis, University of Minnesota, Minneapolis, Minnesota, 1997.
    • (1997)
    • Edelstein, R.L.1
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    • 0141440543 scopus 로고    scopus 로고
    • note
    • 1H NMR.
  • 21
    • 0141552102 scopus 로고    scopus 로고
    • note
    • Both cysteine methyl esters and their free acid counterparts are desirable prenylcysteine analogues, as not all proteins are methylesterified.
  • 24
    • 0141552103 scopus 로고    scopus 로고
    • note
    • Compound 6b and subsequent products therefrom are, in reality, each mixtures of two diastereomers due to the chirality at C-6.
  • 34
    • 0035142179 scopus 로고    scopus 로고
    • Biotinylated prenylated peptides have been prepared via solid-phase synthesis, where biotin-avidin chemistry was utilized in subsequent enzymatic assays (Dolence, E. K.; Dolence, J. M.; Poulter, C. D. Bioconjugate Chem. 2001, 12, 35-43. Liu, L.; Jang, G.-F.; Farnsworth, C.; Yokoyama, K.; Glomset, J. A.; Gelb, M. H. Methods Enzymol. 1995, 250, 189-206).
    • (2001) Bioconjugate Chem. , vol.12 , pp. 35-43
    • Dolence, E.K.1    Dolence, J.M.2    Poulter, C.D.3
  • 35
    • 0029041182 scopus 로고
    • Biotinylated prenylated peptides have been prepared via solid-phase synthesis, where biotin-avidin chemistry was utilized in subsequent enzymatic assays (Dolence, E. K.; Dolence, J. M.; Poulter, C. D. Bioconjugate Chem. 2001, 12, 35-43. Liu, L.; Jang, G.-F.; Farnsworth, C.; Yokoyama, K.; Glomset, J. A.; Gelb, M. H. Methods Enzymol. 1995, 250, 189-206).
    • (1995) Methods Enzymol. , vol.250 , pp. 189-206
    • Liu, L.1    Jang, G.-F.2    Farnsworth, C.3    Yokoyama, K.4    Glomset, J.A.5    Gelb, M.H.6
  • 37
    • 0141775400 scopus 로고    scopus 로고
    • note
    • It should be noted that instead of biotinylation of the amine-containing prenylcysteine compound 12 in Scheme 2, attempts were made to synthesize N-biotinylated cysteine methyl ester and then alkylate its free thiol with bromide 8. This method did not give reproducible results. The potential for oxidation of the cysteinyl sulfhydryl group as well as disulfide formation complicated this reaction. The method shown in Scheme 2 is considerably more reliable.


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