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Volumn 1, Issue 5, 1999, Pages 803-806

β-Lactones as a new class of cysteine proteinase inhibitors: inhibition of hepatitis A virus 3C proteinase by N-Cbz-serine β-Lactone

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EID: 0001014188     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990148r     Document Type: Article
Times cited : (36)

References (49)
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    • β-Lactones such as the antibiotic F-244 (1233A) may acylate a cysteine residue of HMG CoA synthase: Romo, D.; Harrison, P. H. M.; Jenkins, S. I.; Riddoch, R. W.; Park, K.; Yang, H. W.; Zhao, C.; Wright, G. D. Bioorg. Med. Chem. 1998, 6, 1255-1272. Mayer, R. J.; Louis-Flamberg, P.; Elliott, J. D.; Fisher, M.; Leber, J. Biochem. Biophys. Res. Commun. 1990. 169, 610-616.
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    • Omuralide, the β-lactone derived from lactacystin, has been shown to inhibit the 20S proteosome by O-acylation of a threonine residue: (a) Corey, E. J.; Li, W. D. Z. Chem. Pharm. Bull. 1999, 47, 1-10.
    • (1999) Chem. Pharm. Bull. , vol.47 , pp. 1-10
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    • Yang, H.W.1    Romo, D.2
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    • note
    • m of 2.1 mM at pH 7.5; see ref 2.
  • 43
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    • (a) For an example of water attack at the γ-position of homoserine lactone, see: Schwab, J. M.; Ray, T.; Ho, C.-K. J. Am. Chem. Soc. 1989, 111, 1057-1063.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 1057-1063
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  • 47
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    • note
    • 13C), (68 ppm); N-(benzyloxycarbonyl)-S-methyl-L-cysteine 10, (37 ppm); N-(benzyloxycarbonyl)-L-serine ethyl thioester 11, (64 ppm); N-(benzyloxycarbonyl)-L-serine methyl ester 12, (62 ppm); N-(benzyloxycarbonyl)-O-methyl-D-serine 13, (73 ppm). An Inova 600 Varian NMR spectrometer was used to obtain HMQC spectra.


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