The sulfonimidamide as a novel transition state analog for aspartic acid and metallo proteases.

Source:http://linkedlifedata.com/resource/pubmed/id/10386929

Bioorg. Med. Chem. Lett. 1999 Jun 7 9 11 1527-32

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Authors

Schloss JV, Cathers BE

Affiliation

The Department of Medicinal Chemistry, The University of Kansas, Lawrence 66045, USA.

Abstract

We have developed a novel strategy for the preparation of tetrahedral transition state analogs for aspartic acid and metallo-proteases based upon the sulfonimidamide functional group. Our best alpha-des-amino dipeptide analog binds at least 100-fold tighter than the corresponding ground state structure (i.e., amide). A previously unpublished five-membered cyclic sulfonimidamide was also synthesized.

PMID
10386929