A Macrocyclic Peptide Library with a Structurally Constrained Cyclopropane-containing Building Block Leads to Thiol-independent Inhibitors of Phosphoglycerate Mutase.
cyclopropane
genetic code reprogramming
mRNA display
macrocyclic peptide
Journal
Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643
Informations de publication
Date de publication:
01 Sep 2020
01 Sep 2020
Historique:
received:
14
06
2020
revised:
04
07
2020
pubmed:
8
7
2020
medline:
17
6
2021
entrez:
8
7
2020
Statut:
ppublish
Résumé
Here we report the construction of an mRNA-encoded library of thioether-closed macrocyclic peptides by using an N-chloroacetyl-cyclopropane-containing exotic initiator whose structure is more constrained than the ordinary N-chloroacetyl-α-amino acid initiators. The use of such an initiator has led to a macrocycle library with significantly suppressed population of lariat-shaped species compared with the conventional libraries. We previously used a conventional library and identified a small lariat thioether-macrocycle with a tail peptide with a C-terminal free Cys whose sidechain plays an essential role in potent inhibitory activity against a parasitic model enzyme, phosphoglycerate mutase. On the other hand, the cyclopropane-containing macrocycle library has yielded a larger thioether-macrocycle lacking a free Cys residue, which exhibits potent inhibitory activity to the same enzyme with a different mode of action. This result indicates that such a cyclopropane-containing macrocycle library would allow us to access mechanistically distinct macrocycles.
Identifiants
pubmed: 32633882
doi: 10.1002/asia.202000700
pmc: PMC9547493
mid: NIHMS1662945
doi:
Substances chimiques
Cyclopropanes
0
Enzyme Inhibitors
0
Macrocyclic Compounds
0
Peptide Library
0
Peptides
0
Sulfhydryl Compounds
0
cyclopropane
99TB643425
Phosphoglycerate Mutase
EC 5.4.2.11
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
2631-2636Subventions
Organisme : NIH HHS
ID : 1ZIATR000247
Pays : United States
Organisme : KAKENHI
ID : JP20H02866
Organisme : KAKENHI
ID : 16H06444
Organisme : Japan Agency for Medical Research and Development
Organisme : KAKENHI
ID : 19H01014
Organisme : NCATS NIH HHS
Pays : United States
Organisme : KAKENHI
ID : JP18H04382
Organisme : KAKENHI
ID : JP17H04762
Organisme : Platform Project for Supporting Drug Discovery and Life Science Research
ID : JP19am0101090
Organisme : Takeda Science Foundation and the Inamori Foundation
Organisme : AMED
ID : 19ae0101047h0002
Organisme : Intramural NIH HHS
ID : ZIA TR000247
Pays : United States
Organisme : KAKENHI
ID : JP19K22243
Organisme : Japan Society for the Promotion of Science
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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