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Facile Synthesis of (2S,3R)-3-Amino-2-hydroxy-4-(4'-hydroxyphenyl)butanoic Acid. Application to the Synthesis of Inhibitors of Aminopeptidases

  • Moon, Byung-Jo (Department of Biochemistry, College of Natural Sciences, Kyungpook National University) ;
  • Huh, Kyung-Lan (Department of Biochemistry, College of Natural Sciences, Kyungpook National University)
  • Published : 1991.02.20

Abstract

Facile methods are reported for the synthesis of optically pure derivatives of (2S,3R)-3-amino-2-hydroxy-4-(4'-hydroxyphenyl)b utanoic acid. To avoid troublesome synthesis of O-benzyl-N-Boc-D-tyrosine, without the protection of phenolic OH group of tyrosine N-Boc-D-tyrosine methyl ester was reduced with DiBAL to the aldehyde. The aldehyde was converted via the cyanohydrin to (2S,3R)-3-amino-2-hydroxy-4-(4'-hydroxyphenyl)butanoic acid (AHpHBA). The mixture of diastereomers was converted to the corresponding Boc-AHpHBA methyl ester derivatives and separated by chromatography over silica gel. Optically active (2S,3R)-AHpHBA was used to synthesize aminopeptidase inhibitors.

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References

  1. J. Antibiot. v.31 T. Aoyagi;H. Tobe;F. Fojuma;M. Hamada;T. Takeuchi;H. Umezawa
  2. J. Antibiot. v.29 H. Umezawa;T. Aoyagi;H. Suda;M. Hamada;T. Takeuchi
  3. J. Cancer Lett. v.11 H. Blomgren;Wasserman
  4. Biochem. Biophys. Res Commun. v.96 R. K. Barclay;M. A. Phillipps
  5. Biochem. Biophys. Acta v.613 H. Tobe;F. Kojima;T. Aoyagi;H. Umezawa
  6. Peptides: Proceedings of the 6th American Peptide Symposium D. H. Rich;A. S. Boparai;S. Harbeson;B. J. Moon;E. Gross(ed.);J. Meinhofer(ed.)
  7. J. Org. Chem. v.45 D. H. Rich;B. J. Moon;A. S. Boparai
  8. Chemistry of The Amino Acids v.2 J. P. Greenstein;M. Winitz
  9. Bull. Chem. Soc. Jap. v.46 S. Futagawa;T. Inui;T. Shiba
  10. J. Med. Chem. v.27 D. H. Rich;B. J. Moon;S. Harbeson