Potential peptidic proteasome inhibitors by incorporation of an electrophilic trap based on amino acid derived α-substituted sulfonyl fluorides

[Display omitted] Peptido sulfonyl fluoride derivatives were designed and synthesized containing a substituent on the alpha position (αPSFs) with respect to the sulfonyl fluoride electrophilic trap. The chemical reactivity of these α-substituted amino sulfonyl fluorides was studied and compared with...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2017-10, Vol.25 (19), p.5055-5063
Main Authors: Herrero Alvarez, Natalia, van de Langemheen, Helmus, Brouwer, Arwin J., Liskamp, Rob M.J.
Format: Article
Language:English
Subjects:
Amino Acids - chemical synthesis
Amino Acids - chemistry
Amino Acids - pharmacology
Drug Design
Humans
Peptido sulfonyl fluoride
Peptidomimetics - chemical synthesis
Peptidomimetics - chemistry
Peptidomimetics - pharmacology
Proteasome
Proteasome Inhibitors - chemical synthesis
Proteasome Inhibitors - chemistry
Proteasome Inhibitors - pharmacology
Solubility
Sulfinic Acids - chemical synthesis
Sulfinic Acids - chemistry
Sulfinic Acids - pharmacology
Sulfonyl fluoride warhead
α-Substituted sulfonyl fluoride
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Summary:[Display omitted] Peptido sulfonyl fluoride derivatives were designed and synthesized containing a substituent on the alpha position (αPSFs) with respect to the sulfonyl fluoride electrophilic trap. The chemical reactivity of these α-substituted amino sulfonyl fluorides was studied and compared with the previously described β-substituted amino sulfonyl fluorides in order to get a deeper insight into the importance of the immediate structural environment of the sulfonyl fluoride moiety. Unfortunately, the poor solubility of the resulting αPSFs precluded a proper evaluation of their biological activity.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2017.07.019