Enantiopure Synthesis of Alpha-Aminoboronic Acid Derivatives

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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.

-Enantiopure synthesis
-High Yield

Potential Applications:
-Synthesis of alpha-aminoboronic acid derivatives
-Borylation of molecules
-Drug development
Sep 7, 2018
United States
Purdue Office of Technology Commercialization
1801 Newman Road
West Lafayette, IN 47906

Phone: (765) 588-3475
Fax: (765) 463-3486
Email: otcip@prf.org