Pseudopeptides with a centrally positioned alkene-based disulphide bridge mimetic stimulate kallikrein-related peptidase 3 activity

Pseudopeptides based on the kallikrein-related peptidase 3 (KLK3) activating bicyclic peptide “C-4” comprising hydrocarbon-based disulphide bridge mimetics have been synthesized. After investigating different synthetic approaches, the pseudopeptides were successfully cyclized from two L-allylglycine side chains via an alkene ring-closing metathesis reaction during the peptide synthesis. The alkene-linker was formed in a 1 : 1 E/Z isomer ratio. The resulting pseudopeptides were almost as potent as the parent peptide, increasing the activity of KLK3 over four-fold at 200 μg ml−1 (130–140 μM) concentrations.

Weisell, J. (author)
Pakkala, M. (author)
Tadd, A. C. (author)
Hekim, C. (author)
Kallionpaa, R. (author)
Widell, K. (author)
Stenman, U. H. (author)
Koistinen, H. (author)
Narvanen, A. (author)
Vepsalainen, J. (author)
Luthman, Kristina,1953Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology(Swepub:gu)xlutkr (author)
Wallén, Erik A A (author)
Göteborgs universitetInstitutionen för kemi och molekylärbiologi (creator_code:org_t)

In:Medchemcomm: Royal Society of Chemistry (RSC)4:3, s. 549-5532040-25032040-2511

By the author/editor: Meinander, K.; Weisell, J.; Pakkala, M.; Tadd, A. C.; Hekim, C.; Kallionpaa, R.; show more...; Widell, K.; Stenman, U. H.; Koistinen, H.; Narvanen, A.; Vepsalainen, J.; Luthman, Kristin ...; Wallén, Erik A A; show less...

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