Carboxyalkyl Peptide Inhibitors of Kininase II: Chiral Synthesis
Heretofore, carboxyalkyl peptide inhibitors of kininase II (e. g. N-[l-carboxy-3-phenylpropyl]-Ala-Pro, “enalaprilic acid”) have been synthesized by means that yield racemic product. Typically, the secondary amine bond is formed by reacting an amino acid or dipeptide with a 2-keto carboxylic acid ester or imide. The group providing the 2-keto function must be used in excess, and the desired S, S, S isomer must be obtained by resolution procedures. We have developed a procedure whereby enalaprilic acid, RAC-X-64 and related compounds are synthesized stereospecifically and in relatively high yields.
KeywordsSodium Chloride Solution Benzyl Ester Diisopropyl Ether Combine Organic Phasis Isopropyl Ether
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