title: THAL, a sterically unhindered linker for the solid-phase synthesis of acid-sensitive protected peptide acids.
abstract: The 5-(4-hydroxyphenyl)-3,4-ethylenedioxythienyl alcohol (THAL, Thiophene Acid Labile) is described as a new linker for the solid-phase synthesis of peptide carboxylic acids. It is based on the electron-rich 3,4-ethylenedioxythenyl (EDOTn) moiety and allows the obtention of free and tert-butyl-protected peptides by cleavage with 90% and 0.5% TFA, respectively. This very high acid lability makes it useful for the synthesis of sensitive peptides. Free and tert-butyl-protected Leu-enkephalins have been synthesized as models to demonstrate the utility of the linker.
authors: Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028-Barcelona, Spain.
authors: Albert
authors: A
authors: Isidro-Llobet
authors: Ulrik
authors: U
authors: Boas
authors: Knud J
authors: KJ
authors: Jensen
authors: Mercedes
authors: M
authors: Alvarez
authors: Fernando
authors: F
authors: Albericio
mesh_terms: D000143:Acids / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D012117:Resins, Synthetic / Q000138:chemical synthesis / Q000737:chemistry; D012680:Sensitivity and Specificity; D013237:Stereoisomerism
chemical_list: C532786:5-(4-hydroxyphenyl)-3,4-ethylenedioxythienyl alcohol; D000143:Acids; D002264:Carboxylic Acids; D006574:Heterocyclic Compounds, 2-Ring; D010455:Peptides; D012117:Resins, Synthetic