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Hydrazone- and hydrazide-containing N-substituted glycines as peptoid surrogates for expedited library synthesis: Application to the preparation of Tsg101-directed HIV-1 budding antagonists

  1. Author:
    Liu, F.
    Stephen, A. G.
    Adamson, C. S.
    Gousset, K.
    Aman, M. J.
    Freed, E. O.
    Fisher, R. J.
    Burke, T. R.

  2. Author Address

    NCI Frederick, Med Chem Lab, CCR, NIH, Frederick, MD 21702 USA. SAIC Frederick Inc, Prot Chem Lab, Frederick, MD 21702 USA. NCI Frederick, Hiv Drug Resistance Program, CCR, Frederick, MD 21702 USA. USA, Med Res Inst Infect Dis, Frederick, MD 21702 USA.;Burke, TR, NCI Frederick, Med Chem Lab, CCR, NIH, Bldg 376,Boyles St, Frederick, MD 21702 USA.;tburke@helix.nih.gov
    1. Year: 2006
    2. Date: Oct
  2. Journal: Organic Letters
    1. 8
    2. 22
    3. Pages: 5165-5168
  4. Type of Article: Article
  5. ISSN: 1523-7060
  1. Abstract:

    Replacing the Pro6 in the p6(Gag)-derived 9-mer "P-E-P-T-A-(P) under bar -P-E-E" with N-substituted glycine (NSG) residues is problematic. However, incorporation of hydrazone amides ("peptoid hydrazones") can be readily achieved in library fashion. Furthermore, reduction of these hydrazones to N-substituted "peptoid hydrazides" affords a facile route to library diversification. This approach is demonstrated by application to Tsg101-binding compounds designed as potential HIV budding antagonists.

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External Sources

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  2. DOI: 10.1021/ol0622211
  3. View record in Web of Science®
  4. WOS: 000241381800046

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