Chiral synthesis of alpha-aminophosponic acids

Details Chiral synthesis of alpha-aminophosponic acids Chiral synthesis of alpha-aminophosponic acids

1993-09-09

1994-11-08

Morris, Patricia L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Phosphorus esters

558122, 558124, 558166, 558170, 558172, 558173, C07F 940

Patent

active

053628993

ABSTRACT:
A stereospecific method of preparing alpha-aminophosphonic acids and derivatives thereof is provided. A protected amino acid is converted to a acyl aroyl or diacyl peroxide which spontaneously rearranges to form an alpha-amino ester. This rearrangement occurs stereospecifically with retention of configuration. The ester is subsequently converted to an appropriate leaving group and displaced with a phosphite yielding a chiral alpha-aminophosphonic acid or derivative.
Alpha-aminophosphonic acids are useful for the synthesis of peptide analogs that possess a phosphonate linkage in the place of an amide linkage. This substitution can impart protease resistance in therapeutic peptides thereby increasing the serum half-life.

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