STUDIES ON THE ACYLATION OF HYDROXY-FUNCTIONALIZED RESINS USING FMOC AMINO-ACIDS ACTIVATED USING DIISOPROPYLCARBODIIMIDE HOBT OR AS ACID FLUORIDES

The data presented suggests that esterification of hydroxy-functionalized resins with Fmoc-protected amino acids proceeds best in low polarity solvents such as CH2Cl2 and THF and that pyridine, as co-solvent, is a suitable acylation catalyst. This has been demonstrated using DIC/HOBt activation, as well as Fmoc-protected amino acid fluorides which are excellent reagents for rapid, racemization-free acylation of hydroxy-functionalized resins used in solid phase peptide synthesis.