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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 23
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Original Articles

Synthesis of (3R)-Amino-(2S)-Hydroxy Amino Acids for Inhibition of Methionine Aminopeptidase-1

Stacy J. Keding Department of Chemistry, School of Pharmacy, University of Wisconsin-Madison, 425 North Charter Street, Madison, WI, 53706
,
Natalie A. Dales Department of Chemistry, School of Pharmacy, University of Wisconsin-Madison, 425 North Charter Street, Madison, WI, 53706
,
Sejin Lim Department of Chemistry, School of Pharmacy, University of Wisconsin-Madison, 425 North Charter Street, Madison, WI, 53706
,
Danielle Beaulieu Bristol-Myers Squibb Pharmaceutical Research Institute, Wallingford, CT, 06492
&
Daniel H. Rich Department of Chemistry, School of Pharmacy, University of Wisconsin-Madison, 425 North Charter Street, Madison, WI, 53706
Pages 4463-4470 | Received 08 Jun 1998, Published online: 23 Aug 2006
 
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Abstract

(3R)-amino-(2S)-hydroxy heptanoic acid (AHHpA) was synthesized via asymmetric aminohydroxylation and coupled with di-and tripeptides to form three compounds that inhibit MetAP-1 with IC50 values in the low micromolar range.

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