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Volumn 63, Issue 14, 1998, Pages 4767-4778

Synthesis and Evaluation of Tripeptides Containing Asparagine Analogues as Potential Substrates or Inhibitors of Oligosaccharyltransferase

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EID: 0000098929     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9802123     Document Type: Article
Times cited : (17)

References (67)
  • 7
    • 0003832495 scopus 로고
    • Zabicky, J. Z., Ed.; John Wiley & Sons: London, Chapter 13
    • Challis, B. C.; Challis, J. A. In The Chemistry of Amides; Zabicky, J. Z., Ed.; John Wiley & Sons: London, 1970; Chapter 13.
    • (1970) The Chemistry of Amides
    • Challis, B.C.1    Challis, J.A.2
  • 25
    • 85034474100 scopus 로고    scopus 로고
    • 26,27 However, few synthetic details and minimal spectral data were provided
    • 26,27 However, few synthetic details and minimal spectral data were provided.
  • 33
    • 0029087173 scopus 로고
    • A related tripeptide with a β-aspartyl semialdehyde in position 1 predominates as the cyclic aminal; see: Hendrickson, T. L.; Imperiali, B. Biochemistry 1995, 34, 9444-9450.
    • (1995) Biochemistry , vol.34 , pp. 9444-9450
    • Hendrickson, T.L.1    Imperiali, B.2
  • 44
    • 85034480487 scopus 로고    scopus 로고
    • note
    • 6 over this concentration range. Moreover, the observed NOEs, measured at both 5 and 10 mM for 10, were not concentration dependent. These data indicate that the NOEs were due to intramolecular interactions and not due to intermolecular peptide aggregation.
  • 51
    • 85034459510 scopus 로고    scopus 로고
    • note
    • γNH, in Table 2 of ref 8 were inadvertently transposed. This neccesarily alters the conclusions regarding the solution conformation of the nonsubstrate peptide 10. The NMR data for the other peptides in ref 8 appear correct, and the overall conclusion that substrate peptides can adopt the Asx-turn in solution remains the same. We thank Professor Imperiali for helpful correspondence.
  • 52
    • 85034461996 scopus 로고    scopus 로고
    • note
    • 20 Because of this particular amino acid substitution, this peptide is unlikely to form an Asx-turn structure, yet it still has a strong affinity for binding to OST.
  • 56
    • 85034485079 scopus 로고    scopus 로고
    • note
    • It was repeatedly observed that the diazoketone-containing peptide 7 showed slight activity as an OST acceptor substrate. The apparent ability of the diazoketone-containing peptide 7 to serve as a weak OST substrate is an intriguing but, as yet, unexplained observation.
  • 58
    • 85034461222 scopus 로고    scopus 로고
    • note
    • Boc-DONV-OBn was also synthesized and tested as an inactivator of OST. Interestingly, it also shows slight inhibition toward OST-catalyzed glycosylation. At 10 mM, it shows even more inhibition than the diazoketone 7 (data not shown), suggesting that both 7 and Boc-DONV-OBn may be similar to MMTS and act as nonspecific inactivators of OST. Possibly, they all react with a cysteine that is not in the OST active site, and this cysteine has a structural role rather than a catalytic function.
  • 61


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.