The Boc/Solid Phase Synthesis of Glu-Abu(P)-Leu

Abstract

The synthesis of the 4-phosphono-2-aminobutanoyl-containing tripeptide , H- Glu -Abu(P)- Leu-OH.CF₃C0₂H was accomplished by the use of Boc-Abu(PO₃Me₂)-OH in Boc /solid phase peptide synthesis. Peptide synthesis was performed by using Boc-Leu-polystyrene as the polymer support with the peptide assembled by the use of 1H-benzotriazol-1-yloxytris(pyrro1idin-1-yl) phosphonium hexafluorophosphate ( PyBOP^R ) for the coupling of Boc amino acids and 50% CF₃C0₂H/CH₂C1₂ for cleavage of the Boc group from the Boc -peptide after each coupling cycle. The protected peptide was cleaved from the polymer support by hydrogen bromide in trifluoroacetic acid and final cleavage of the methyl groups from Glu-Abu(PO₂Me₂)-Leu was effected by silylitic treatment with 30% bromotrimethylsilane in acetonitrile.