Synthesis and bio-assay of RCM-derived Bowman-Birk inhibitor analogues.
Bowman-Birk inhibitor analogues containing 2, 3 and 4-carbon analogues of the natural disulfide were synthesised via solid phase microwave-assisted RCM and found to have K(i) values against chymotrypsin in the low to sub-micromolar range, the best replacement for the disulfide arising from the linkage by RCM of two l-homoallylglycine residues.
Miles
Steven M
SM
Department of Chemistry, Imperial College London, South Kensington Campus, London, UKSW7 2AZ.
Leatherbarrow
Robin J
RJ
Marsden
Stephen P
SP
Coates
William J
WJ
D000818:Animals; D002417:Cattle; D002918:Chymotrypsin / Q000037:antagonists & inhibitors / Q000378:metabolism; D004220:Disulfides / Q000737:chemistry; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014358:Trypsin Inhibitor, Bowman-Birk Soybean / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D004220:Disulfides; D010456:Peptides, Cyclic; D014358:Trypsin Inhibitor, Bowman-Birk Soybean; D002918:Chymotrypsin