PMID: 9650718Jul 3, 1998Paper

Characterization of the thiol/disulfide chemistry of peptides corresponding to the 603-609 disulfide loop of the human immunodeficiency virus (HIV) envelope glycoprotein gp41

The Journal of Peptide Research : Official Journal of the American Peptide Society
D L RabensteinJ Gu

Abstract

The redox chemistry of two synthetic model peptides for the 603-609 disulfide loop found in envelope glycoprotein gp41 of the human immunodeficiency virus type 1 (HIV-1) are reported. The two peptides: N-Ac-Trp-Gly-Cys-Ser-Gly-Lys-Leu-Ile-Cys-Thr-Thr-NH2 (I) and N-Ac-Trp-Gly-Cys-Ser-Gly-Arg-His-Ile-Cys-Thr-Thr-NH2 (II) were synthesized by the solid phase method. Peptide I corresponds to amino acids 601-611 of gp41 of the North American/European strain of HIV-1. Peptide II incorporates amino acid replacements frequent in African HIV-1 isolates. The redox chemistry of the disulfide bonds in the two peptides was characterized in aqueous and aqueous/urea solution by studying their thiol-disulfide exchange reactions with the tripeptide glutathione (GSH). GSH reacts with the disulfide bonds to form mixed disulfides, which in turn react with another molecule of GSH to give the dithiol form of the peptide and GSSG. Equilibrium constants were determined for each step and for the overall reduction reactions. Redox potentials of -0.246V and -0.241V were calculated from the equilibrium constants for the disulfide bonds in peptides I and II in aqueous solution at 25 degrees C and pH 7.0. The overall equilibrium constants are less in 8 M ure...Continue Reading

References

Sep 28, 1990·Science·H MitsuyaS Broder
Jan 1, 1991·Annual Review of Biophysics and Biophysical Chemistry·H J Dyson, P E Wright
May 10, 1994·Proceedings of the National Academy of Sciences of the United States of America·H J RyserG J DiSciullo

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