Abstract
Bestatin (ubenimex) is a dipeptide that can treat a variety of diseases. Over the last thirty years synthetic chemists have developed an assortment of routes to optically pure (-)-Bestatin. Many strategies include the use of pure starting materials like sugars and amino acids. In addition, the utilization of chiral auxiliary groups have been implemented to achieve an increase in stereoselectivity and to simplify the purification process. Lastly, asymmetric catalysis using enzymes or inorganic catalysts has also been used to afford the desired stereochemistry. This review will cover 23 synthetic strategies to (-)-Bestatin through the year 2005.
Keywords: 3-amino-2-hydroxy-4-phenylbutanoic acid(AHPBA), Optically Active Amino Acids, Chiral Sugars, Chiral Auxiliary Groups, Catalysis
Current Organic Chemistry
Title: Bestatin: Three Decades of Synthetic Strategies
Volume: 11 Issue: 5
Author(s): Brent D. Feske
Affiliation:
Keywords: 3-amino-2-hydroxy-4-phenylbutanoic acid(AHPBA), Optically Active Amino Acids, Chiral Sugars, Chiral Auxiliary Groups, Catalysis
Abstract: Bestatin (ubenimex) is a dipeptide that can treat a variety of diseases. Over the last thirty years synthetic chemists have developed an assortment of routes to optically pure (-)-Bestatin. Many strategies include the use of pure starting materials like sugars and amino acids. In addition, the utilization of chiral auxiliary groups have been implemented to achieve an increase in stereoselectivity and to simplify the purification process. Lastly, asymmetric catalysis using enzymes or inorganic catalysts has also been used to afford the desired stereochemistry. This review will cover 23 synthetic strategies to (-)-Bestatin through the year 2005.
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Cite this article as:
Feske D. Brent, Bestatin: Three Decades of Synthetic Strategies, Current Organic Chemistry 2007; 11 (5) . https://dx.doi.org/10.2174/138527207780059277
DOI https://dx.doi.org/10.2174/138527207780059277 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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