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Silanediol-based inhibitor of thermolysin.

The first silanediol inhibitor of thermolysin is reported, prepared by analogy with the Grobelny/Bartlett phosphinate inhibitor. A Cbz group on nitrogen proved to be unstable to the triflic acid mediated silanediol deprotection and was replaced with a dihydrocinnamoyl group. The silanediol was prepared in high purity by hydrolysis of a difluorosilane intermediate and proved to be an effective inhibitor, differing from the phosphinate by a factor of 4 (K(i)=41nM).[1]

References

  1. Silanediol-based inhibitor of thermolysin. Kim, J., Glekas, A., McN Sieburth, S. Bioorg. Med. Chem. Lett. (2002) [Pubmed]
 
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