1-Aminocyclopropaneboronic acid: synthesis and incorporation into an inhibitor of hepatitis C virus NS3 protease.
The previously unreported alpha,alpha-disubstituted 1-aminoboronate esters have potential utility in peptidomimetic design, particularly against serine protease targets. A concise synthesis of 1-aminocyclopropaneboronate pinanediol ester is reported, and a peptidyl derivative is shown to have modest affinity (K(i) = 1.6 microM) for hepatitis C NS3 protease.
Priestley
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Department of Chemical and Physical Sciences, DuPont Pharmaceuticals Company, P.O. Box 80500, Wilmington, Delaware 19880, USA. e.scott.priestley@dupontpharma.com
Decicco
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CP
D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D006526:Hepatitis C / Q000201:enzymology*; D009842:Oligopeptides / Q000737:chemistry*; D011480:Protease Inhibitors / Q000138:chemical synthesis*; D017361:Viral Nonstructural Proteins / Q000037:antagonists & inhibitors*; D012697:Serine Endopeptidases; D043583:Nucleoside-Triphosphatase; D053487:DEAD-box RNA Helicases; D000085242:Viral Proteases
D001897:Boronic Acids; D003521:Cyclopropanes; D009842:Oligopeptides; D011480:Protease Inhibitors; D017361:Viral Nonstructural Proteins; C415682:1-aminocyclopropaneboronic acid; C084422:NS3 protein, hepatitis C virus; D012697:Serine Endopeptidases; D043583:Nucleoside-Triphosphatase; D053487:DEAD-box RNA Helicases; D000085242:Viral Proteases