title: Facile SPS of peptides having C-terminal Asn and Gln.
abstract: Attachment of Fmoc-asparagine or glutamine to p-alkoxybenzyl alcohol type resins has always been difficult and not very effective. A very simple and effective method for the preparation of peptides terminating in asparagine or glutamine is described. The method involves quantitative attachment of Fmoc-Asp-OtBu or Fmoc-Glu-OtBu via their side-chain carboxyl group to a resin functionalized with our TMBPA linker for peptide amides. Peptide synthesis is performed using our standard Fmoc chemistry, and treatment with acid, e.g. TFA/DCM/scavenger mixtures, releases the Asn or Gln peptides.
authors.affiliation: Hoechst AG, Frankfurt am Main.
authors.forename: G
authors.initials: G
authors.lastname: Breipohl
authors.forename: J
authors.initials: J
authors.lastname: Knolle
authors.forename: W
authors.initials: W
authors.lastname: Stüber
mesh_terms: D000596:Amino Acids; D001216:Asparagine; D005449:Fluorenes; D005973:Glutamine; D008752:Methylene Chloride; D010455:Peptides / Q000138:chemical synthesis*; D014269:Trifluoroacetic Acid
chemical_list: D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010455:Peptides; D005973:Glutamine; C064377:N-fluorenylmethyloxycarbonyl-((carboxyethyl-2,4-dimethoxyphenyl)-4'-methoxyphenyl)methylamine; D008752:Methylene Chloride; D001216:Asparagine; D014269:Trifluoroacetic Acid