Solid-phase synthesis of a library based on biphenyl-containing trypsin-like serine protease inhibitors.
The solid-phase synthesis of a library based on an unusual biphenyl-containing trypsin-like serine protease inhibitor is described. Key to this effort was the synthesis of a highly functionalized aryl boronic acid reagent which required the development of a novel and efficient method to convert a triflate to a pinacolboronate in large scale.
Shi
Shuhao
S
Bristol-Myers Squibb Company, 5 Research Parkway, Wallingford, CT 06492, USA. shij@bms.com
Zhu
Shirong
S
Gerritz
Samuel W
SW
Rachwal
Bogumila
B
Ruan
Zheming
Z
Hutchins
Robert
R
Kakarla
Ramesh
R
Sofia
Michael J
MJ
Sutton
James
J
Cheney
Daniel
D
D001224:Aspartic Acid / Q000494:pharmacology; D001713:Biphenyl Compounds / Q000494:pharmacology*; D017320:HIV Protease Inhibitors / Q000494:pharmacology; D008407:Mast Cells; D008969:Molecular Sequence Data; D019151:Peptide Library; D011480:Protease Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D011487:Protein Conformation / Q000187:drug effects; D012694:Serine / Q000494:pharmacology; D012697:Serine Endopeptidases / Q000187:drug effects*; D013329:Structure-Activity Relationship; D013379:Substrate Specificity
D001224:Aspartic Acid; D001713:Biphenyl Compounds; D017320:HIV Protease Inhibitors; D019151:Peptide Library; D011480:Protease Inhibitors; D012694:Serine; D012697:Serine Endopeptidases; C114880:trypsin-like serine protease; C010574:biphenyl