- Novel peptide isosteres that were designed to inhibit the binding of the HIV surface glycoprotein (gp120) to the T cell surface glycoprotein CD4
-
The cis- and trans-isomers of (2S)-2-[3′(RS)-3′-benzyl-3′-benzyloxycarbonylprop-1′- enyl]-N-methoxycarbonylcarbonylpyrrolidines have been prepared from a Wittig reaction between (S)-N-Boc-prolinal and the phosphorus ylide from (2RS)-3-iodo-2-benzyl-1-triisopropylsilyloxypropane. In addition, (2S)-N-methoxycarbonylcarbonyl-2-[(3′RS)-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.
- Drew, Michael G. B.,Gorsuch, Stephen,Mann, John,Yoshida, Shimon
-
p. 1627 - 1636
(2007/10/03)
-
- Synthesis and biological activity of acylated and telomerized peptides as potential HIV-fixation inhibitors
-
In order to inhibit the gp 120-CD4 glycoprotein interaction, a key step of the HIV-infection, we have synthesized a series of N-acylated peptides containing sequences identified in both the viral and lymphocytic proteins, (SDFR, SDAR, RFDSAARFDS, DRADSRRS, PSKLNDRADSRRSLWD, ASTTTNYT). An hydrophobic moiety (capryloyl, palmitoyl acrylamidoundecanoyl) was introduced in the last step of interative synthesis, in homogeneous or solid phase. The acryloyl-containing compounds were then telomerized under UV irradiation (DPn observed: 2 to 6). The biological evaluation shown an antiviral effect in vitro for telomerized peptides containing amino diacids such as Glu and Asp.
- Lacoux,Barragan,Dewynter,Leydet,Roque,Montero
-
p. 767 - 773
(2007/10/03)
-
