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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 27, Number 8
BKCSDE 27(8)
August 20, 2006 

Stereospecific Synthesis of the (2R,3S)- and (2R,3R)-3-Amino-2-hydroxy-4-phenylbutanoic Acids from D-Glucono-δ-lactone
Jin Hwan Lee, Jin Hyo Kim, Byong Won Lee, Woo Duck Seo, Min Suk Yang, Ki Hun Park*
α-Hydroxy-β-amino acid, (2R,3S)-AHPBA, BACE 1, Bestatin stereoisomer, D-Glucono-δ-lactone.
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-δ-lactone. Both AHPBAs are the structural key units of KMI derivatives which are the potent inhibitors of BACE 1 (β-secretase) and HIV protease. Additionally, the obtained AHPBAs 1 and 3 are converted to dipeptides of bestatin stereoisomers 2 and 4.
1211 - 1218
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