Abstract
The simple model substrate AC-L-Abu(PO3H2)- NHMe was prepared by the use of the protected 4( diethylphosphono ) butanoic acid derivative Boc -Abu(PO3Et2)-OH in the Boc mode of solution phase peptide synthesis. The protected peptide model Ac-Abu(P03Et2)- NHMe was prepared by initial reaction of the isobutoxycarbonyl mixed anhydride of Boc-Abu(PO3Et2)-OH with N-methylamine followed by cleavage of the Boc group from Boc -Abu(PO3Et2)- NHMe with 4 M HCl/dioxan and N- acetylation of H-Abu(PO3Et2)-NHMe.HCl with the isobutoxycarbonyl mixed anhydride of acetic acid. Cleavage of the phosphonate ethyl groups was effected with 33% hydrogen bromidelacetic acid or 10% bromotrimethylsilane/acetonitrile to give AC-L-Abu(PO3H2)-NHMe in near-quantitative yield.
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