p-Chloropropynyl Phenylalanine, a Versatile Non-Canonical Amino Acid for Co-Translational Peptide Macrocyclization and Side Chain Diversification.

Amino Acids / chemistry Phenylalanine / metabolism Amino Acyl-tRNA Synthetases / metabolism Peptides / chemistry RNA, Transfer / metabolism
aminoacyl-tRNA synthetases in vitro translation non-canonical amino acids peptide macrocycles thiol reactivity

Journal

Chembiochem : a European journal of chemical biology
ISSN: 1439-7633
Titre abrégé: Chembiochem
Pays: Germany
ID NLM: 100937360

Informations de publication

Date de publication:
01 06 2023
Historique:
revised: 07 04 2023
received: 11 01 2023
medline: 2 6 2023
pubmed: 9 5 2023
entrez: 8 5 2023
Statut: ppublish

Résumé

Macrocyclization has proven to be a beneficial strategy to improve upon some of the disadvantages of peptides as therapeutics. Nevertheless, many peptide cyclization strategies are not compatible with in vitro display technologies like mRNA display. Here we describe the novel amino acid p-chloropropynyl phenylalanine (pCPF). pCPF is a substrate for a mutant phenylalanyl-tRNA synthetase and its introduction into peptides via in vitro translation leads to spontaneous peptide macrocyclization in the presence of peptides containing cysteine. Macrocyclization occurs efficiently with a wide variety of ring sizes. Moreover, pCPF can be reacted with thiols after charging onto tRNA, enabling the testing of diverse ncAAs in translation. The versatility of pCPF should facilitate downstream studies of translation and enable the creation of novel macrocyclic peptide libraries.

Identifiants

DOI: 10.1002/cbic.202300020 PMID: 37156744
pubmed: 37156744
doi: 10.1002/cbic.202300020
doi:

Substances chimiques

Amino Acids 0
Phenylalanine 47E5O17Y3R
Amino Acyl-tRNA Synthetases EC 6.1.1.-
Peptides 0
RNA, Transfer 9014-25-9

Types de publication

Journal Article Research Support, U.S. Gov't, Non-P.H.S. Research Support, N.I.H., Extramural

Langues

eng

Sous-ensembles de citation

IM

Pagination

e202300020

Subventions

Organisme : NCI NIH HHS
ID : R03 CA259876
Pays : United States

Informations de copyright

© 2023 The Authors. ChemBioChem published by Wiley-VCH GmbH.

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Auteurs

H Estheban Osorio Franco (HE)

Chemistry, Virginia Commonwealth University, 1001 W Main St, Richmond, VA-23284, USA.
Massey Cancer Center, Virginia Commonwealth University, 1001 W Main St, Richmond, VA-23284, USA.

Anthony V Le (AV)

Chemistry, Virginia Commonwealth University, 1001 W Main St, Richmond, VA-23284, USA.
Massey Cancer Center, Virginia Commonwealth University, 1001 W Main St, Richmond, VA-23284, USA.

Nathan Y Chang (NY)

Chemistry, Virginia Commonwealth University, 1001 W Main St, Richmond, VA-23284, USA.
Massey Cancer Center, Virginia Commonwealth University, 1001 W Main St, Richmond, VA-23284, USA.

Matthew C T Hartman (MCT)

Chemistry, Virginia Commonwealth University, 1001 W Main St, Richmond, VA-23284, USA.
Massey Cancer Center, Virginia Commonwealth University, 1001 W Main St, Richmond, VA-23284, USA.
ORCID: 0000-0003-0210-1422

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Classifications MeSH

questionsmedicales.fr › Acides aminés, peptides et protéines › Acides aminés › p-Chloropropynyl Phenylalanine, a Versatile...
questionsmedicales.fr › Acides aminés, peptides et protéines › Acides aminés › Acides aminés essentiels › Phénylalanine › p-Chloropropynyl Phenylalanine, a Versatile...
questionsmedicales.fr › Enzymes et coenzymes › Enzymes › Ligases › Carbon-oxygen ligases › Amino acyl-tRNA synthetases › p-Chloropropynyl Phenylalanine, a Versatile...
questionsmedicales.fr › Acides aminés, peptides et protéines › Peptides › p-Chloropropynyl Phenylalanine, a Versatile...
questionsmedicales.fr › Acides nucléiques, nucléotides et nucléosides › Acides nucléiques › ARN › ARN de transfert › p-Chloropropynyl Phenylalanine, a Versatile...