Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Stereospecific Synthesis of the (2R,3S)- and (2R,3R)-3-Amino-2-hydroxy-4-phenylbutanoic Acids from D-Glucono-δ-lactone

  • Lee, Jin Hwan (Division of Applied Life Science (BK21 Program), Department of Agricultural Chemistry, Research Institute of Life Science, Gyeongsang National University) ;
  • Kim, Jin Hyo (Division of Applied Life Science (BK21 Program), Department of Agricultural Chemistry, Research Institute of Life Science, Gyeongsang National University) ;
  • Lee, Byong Won (Division of Applied Life Science (BK21 Program), Department of Agricultural Chemistry, Research Institute of Life Science, Gyeongsang National University) ;
  • Seo, Woo Duck (Division of Applied Life Science (BK21 Program), Department of Agricultural Chemistry, Research Institute of Life Science, Gyeongsang National University) ;
  • Yang, Min Suk (Division of Applied Life Science (BK21 Program), Department of Agricultural Chemistry, Research Institute of Life Science, Gyeongsang National University) ;
  • Park, Ki Hun (Division of Applied Life Science (BK21 Program), Department of Agricultural Chemistry, Research Institute of Life Science, Gyeongsang National University)
  • Published : 2006.08.20
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Abstract

The enantiomerically pure (2R,3S)- and (2R,3R)-3-amino-2-hydroxy-4-phenylbutanoic acids (AHPBA) 1 and 3 are readily obtained from D-glucono-a-lactone. Both AHPBAs are the structural key units of KMI derivatives which are the potent inhibitors of BACE 1 ($\beta$-secretase) and HIV protease. Additionally, the obtained AHPBAs 1 and 3 are converted to dipeptides of bestatin stereoisomers 2 and 4.

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References

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