Abstract
The furyl group of (2-furyl)-L-alanine-containing peptides obtained from Fmoc solid-phase synthesis is partially degraded to several by-products during the final TFA-mediated deprotection in the presence of cation scavengers such as ethanedithiol and propanedithiol. The major by-product corresponds to a bis-dithioacetale formed after acidic hydrolysis of the furyl group. We examined several cleavage conditions and found that cleavage cocktails containing water and triisopropylsilane or 3,6-dioxa-1,8- octanedithiol (DODT) in trifluoroacetic acid are sufficient to minimize the side reaction.
Keywords: peptide synthesis, scavenger, thiol, (2-furyl)-l-alanine, cleavage, dithioacetale
Protein & Peptide Letters
Title: Stability and Cleavage Conditions of (2-Furyl)-L-Alanine-Containing Peptides
Volume: 11 Issue: 6
Author(s): Axel Schulz, Annette Busmann, Enno Kluver, Matthias Schnebel and Knut Adermann
Affiliation:
Keywords: peptide synthesis, scavenger, thiol, (2-furyl)-l-alanine, cleavage, dithioacetale
Abstract: The furyl group of (2-furyl)-L-alanine-containing peptides obtained from Fmoc solid-phase synthesis is partially degraded to several by-products during the final TFA-mediated deprotection in the presence of cation scavengers such as ethanedithiol and propanedithiol. The major by-product corresponds to a bis-dithioacetale formed after acidic hydrolysis of the furyl group. We examined several cleavage conditions and found that cleavage cocktails containing water and triisopropylsilane or 3,6-dioxa-1,8- octanedithiol (DODT) in trifluoroacetic acid are sufficient to minimize the side reaction.
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Cite this article as:
Schulz Axel, Busmann Annette, Kluver Enno, Schnebel Matthias and Adermann Knut, Stability and Cleavage Conditions of (2-Furyl)-L-Alanine-Containing Peptides, Protein & Peptide Letters 2004; 11 (6) . https://dx.doi.org/10.2174/0929866043406238
DOI https://dx.doi.org/10.2174/0929866043406238 |
Print ISSN 0929-8665 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5305 |
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