[Hydrogen peroxide for disulfide bridge formation in the synthesis of peptides with the sequence of the immunodominant epitope of HIV gp41 glycoprotein].

Abstract

A simple, rapid, and highly efficient method for intramolecular disulfide formation in tryptophan-containing peptides using hydrogen peroxide was elaborated. Solid phase synthesis of the peptide fragment corresponding to 601-617 sequence of transmembrane gp41 glycoprotein of HIV-1 was performed by Fmoc-technique. Coupling of Fmoc-Asn-OH by DCC-HOBt method was shown to be accompanied by a side reaction of dehydration of asparagine amide function with the formation of side product (22%) containing 3-cyanoalanine residue. This side reaction was not observed, when Fmoc-Asn-OH was coupled in the form of its p-nitrophenyl ester and with HOBt as a catalyst.

• Authors: M V Sidorova, E V Kudriavtseva, M L Antopol'skiĭ, M E Pal'keeva, M V Ovchinnikov, Zh D Bespalova
• Journal: Bioorganicheskaia khimiia (Bioorg Khim) Vol. 22 Issue 4 Pg. 273-9 (Apr 1996) ISSN: 0132-3423 [Print] Russia (Federation)
• Vernacular Title: Perekis' vodoroda dlia zamykaniia disul'fidnykh sviazeĭ v sinteze peptidov posledovatel'nosti immunodominantnogo epitopa glikoproteina gp41 VICh.
• PMID: 8768265 (Publication Type: English Abstract, Journal Article)

Chemical References

• Disulfides
• HIV Envelope Protein gp41
• Immunodominant Epitopes
• Peptide Fragments
• Hydrogen Peroxide

Topics

• Amino Acid Sequence
• Disulfides (chemistry)
• HIV Envelope Protein gp41 (immunology)
• HIV-1 (chemistry)
• Hydrogen Peroxide (chemistry)
• Immunodominant Epitopes (chemistry, immunology)
• Molecular Sequence Data
• Peptide Fragments (chemical synthesis)