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DOI: 10.1039/A800756J (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 1627-1636

Novel peptide isosteres that were designed to inhibit the binding of the HIV surface glycoprotein (gp120) to the T cell surface glycoprotein CD4

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Michael G. B. Drew, Stephen Gorsuch, John Mann and Shimon Yoshida

Abstract

The cis- and trans-isomers of (2S[hair space])-2-[3′(RS[hair space])-3′-benzyl-3′-benzyloxycarbonylprop-1′-enyl]-N-methoxycarbonylcarbonylpyrrolidines have been prepared from a Wittig reaction between (S[hair space])-N-Boc-prolinal and the phosphorus ylide from (2RS[hair space])-3-iodo-2-benzyl-1-triisopropylsilyloxypropane. In addition, (2S[hair space])-N-methoxycarbonylcarbonyl-2-[(3′RS[hair space])-1-oxo-3′-benzyl-3′-benzyloxycarbonylpropyl]pyrrolidine was prepared from the cis-alkene produced in the Wittig reaction. These were intended as peptide isosteres of the known inhibitors of HIV-lymphocyte binding N-methoxycarbonylcarbonylprolylphenylalanyl benzyl esters, but did not possess such activity.

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