R-1-Acetamido-2-phenylethaneboronic acid. A specific transition-state analog for chymotrypsin

Design of serine protease inhibitors with conformation restricted by amino acid side-chain-side-chain CH/? interaction

“…For example, Ac-Pro-Ala-Pro-phenylalaninal and boroPhe derivatives were found to be effective inhibitors of chymotrypsin. 6,7 In addition to the substrate structure for chymotrypsin, these inhibitors contain the aldehyde group and boric acid, respectively, as a key functional element for inhibition. However, these are not always favorable as therapeutics because of their toxicity, and to date only a few synthetic inhibitors are available clinically.…”

Aminophosphonic and Aminoboronic Acids as Key Elements of a Transition State Analogue Inhibitor of Enzymes

“…Matteson et al developed a stereoselective homologation of pinanediol boronic esters with (dichloromethyl)lithium to chiral a-chloro boronic esters 51) and expanded this reaction to the synthesis of (R)-lacetamido-2-phenylethanebofonic acid (30), a boronic acid analogue of N-acetyl-L-phenylalanine. 52 ) Compound 30 competitively inhibited chymotrypsin with an inhibition constant of 2.1 fJM. The affinity was 14,000 times higher than that for the corresponding substrate N-acetyl-Lphenylalanine amide, suggesting that 30 served as a transition state analogue inhibitor.…”

Synthesis of Novel α‐Aminoboronate Complexes of Aminoboranes and Aminocyanoboranes

“…[4][5][6] In this context, new effective methods to prepare amino and related boron compounds will have a tremendous impact on synthetic, bioinorganic, and pharmaceutical chemistry. [7][8][9][10][11][12] The first synthesis of an α-amidoboronic ester was reported by Matteson et al, [13] and remains the standard method for synthesis of α-aminoboronic acids; however, it is a multistep method and is time consuming.…”