THAL, a sterically unhindered linker for the solid-phase synthesis of acid-sensitive protected peptide acids.
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.
Isidro-Llobet
Albert
A
Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028-Barcelona, Spain.
Boas
Ulrik
U
Jensen
Knud J
KJ
Alvarez
Mercedes
M
Albericio
Fernando
F
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
C532786:5-(4-hydroxyphenyl)-3,4-ethylenedioxythienyl alcohol; D000143:Acids; D002264:Carboxylic Acids; D006574:Heterocyclic Compounds, 2-Ring; D010455:Peptides; D012117:Resins, Synthetic