title: Stability and cleavage conditions of (2-furyl)-L-alanine-containing peptides.
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.
authors.affiliation: IPF PharmaCeuticals GmbH, Feodor-Lynen Strasse 31, 30625 Hannover, Germany. a.schulz@ipf-pharmaceuticals.de
authors.forename: Axel
authors.initials: A
authors.lastname: Schulz
authors.forename: Annette
authors.initials: A
authors.lastname: Busmann
authors.forename: Enno
authors.initials: E
authors.lastname: Klüver
authors.forename: Matthias
authors.initials: M
authors.lastname: Schnebel
authors.forename: Knut
authors.initials: K
authors.lastname: Adermann
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives*; D002851:Chromatography, High Pressure Liquid; D005019:Ethyl Ethers / Q000378:metabolism; D010446:Peptide Fragments / Q000378:metabolism*; D012821:Silanes / Q000378:metabolism; D013438:Sulfhydryl Compounds / Q000378:metabolism; D014269:Trifluoroacetic Acid
chemical_list: C471080:3,6-dioxa-1,8-octanedithiol; D005019:Ethyl Ethers; D010446:Peptide Fragments; D012821:Silanes; D013438:Sulfhydryl Compounds; D014269:Trifluoroacetic Acid; D000409:Alanine