Abstract
Peptide and amino acid conjugates of (4 R)- and (4 S)-4-aminocyclophosphamides (4-NH 2-CPA, 3) were designed as prodrug forms of phosphoramide mustard. Four diastereomers of Boc-Phe-4-NH-CPA ( 6) were synthesized stereospecifically from homoserine ( R or S) and the protection strategy was optimized for the homoserine hydroxyl group during the construction of the 1,3,2-oxazaphosphorinane ring. The Phe-4-NH-CPA isomers of the trans-configuration ((2 S,4 R)- and (2 R,4 S)-) were found to be less stable than the corresponding isomers of the cis-configuration ((2 R,4 R)- and (2 S,4 S)-) and to undergo epimerization of the C-4 chiral center in the presence of 25% TFA used during Boc deprotection. The synthetic route developed should be applicable to the synthesis of a variety of peptide and amino acid conjugates of 4-aminocyclophosphamide.
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