Abstract
The stereoselective synthesis of ( S)-2-amino- N α -(9-fluorenylmethoxycarbonyl)-3-( α 4,3- O- bis- tert-butoxycarbonylpyridoxamin-5-yl)propanoic acid ( 4) was accomplished from pyridoxamine dihydrochloride. A key step is the stereoselective alkylation of (−)pseudoephedrine glycinamide with the pyridoxamine bromide 7. Amenability of the amino acid derivative 4 to solid phase methodology was demonstrated by its incorporation into a synthetic hexapeptide. Critical to the orthogonal protection of the pyridoxamine moiety is the in situ acetylation of the C3-hydroxyl group during peptide assembly.
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