Enantiopure Synthesis of Alpha-Aminoboronic Acid Derivatives

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2019-NEGI-68371
Alpha-aminoboronic acids have been shown to possess anti-bacterial, anti-cancer, and anti-viral activity. This has resulted in increasing interest in developing alpha-aminoboronic acid derivatives for pharmaceutical application. However, this is difficult due to the nature of the chemical synthesis pathway. It is often desired to produce a specific enantiomer of alpha-aminoboronic acid because the activity of the molecule can differ between enantiomers. Unfortunately, there are limited number of synthesis pathways to produce enantiospecific derivatives.

Researchers at Purdue University have developed a synthesis pathway to produce enantiopure N-substituted quaternary alpha-aminoboronic esters. This borylation pathway can be used for molecules with multiple chiral centers. Experiments showed that alpha-aminoboronic acid derivatives were able to be produced with 82 to 99 percent yield and over 99 percent enatiopurity.

Advantages:
-Enantiopure synthesis
-High Yield

Potential Applications:
-Synthesis of alpha-aminoboronic acid derivatives
-Borylation of molecules
-Drug development
Sep 7, 2018
Provisional-Patent
United States
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