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http://dx.doi.org/10.5012/bkcs.2006.27.8.1211

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)
Publication Information
Bulletin of the Korean Chemical Society / v.27, no.8, 2006 , pp. 1211-1218 More about this Journal
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.
Keywords
$\alpha$-Hydroxy-$\beta$-amino acid; (2R,3S)-AHPBA; BACE 1; Bestatin stereoisomer; D-Glucono-$\delta$-lactone;
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