Noncovalent Peptide Stapling Using Alpha-Methyl-l-Phenylalanine for α-Helical Peptidomimetics.

Humans Relaxin / chemistry Peptidomimetics Receptors, G-Protein-Coupled / chemistry Protein Conformation, alpha-Helical Phenylalanine

Journal

Journal of the American Chemical Society
ISSN: 1520-5126
Titre abrégé: J Am Chem Soc
Pays: United States
ID NLM: 7503056

Informations de publication

Date de publication:
20 09 2023
Historique:
medline: 21 9 2023
pubmed: 13 7 2023
entrez: 13 7 2023
Statut: ppublish

Résumé

Peptides and peptidomimetics are attractive drug candidates because of their high target specificity and low-toxicity profiles. Developing peptidomimetics using hydrocarbon (HC)-stapling or other stapling strategies has gained momentum because of their high stability and resistance to proteases; however, they have limitations. Here, we take advantage of the α-methyl group and an aromatic phenyl ring in a unique unnatural amino acid, α-methyl-l-phenylalanine (αF), and propose a novel, noncovalent stapling strategy to stabilize peptides. We utilized this strategy to create an α-helical B-chain mimetic of a complex insulin-like peptide, human relaxin-3 (H3 relaxin). Our comprehensive data set (

Identifiants

DOI: 10.1021/jacs.3c02743 PMID: 37439676
pubmed: 37439676
doi: 10.1021/jacs.3c02743
doi:

Substances chimiques

Relaxin 9002-69-1
Peptidomimetics 0
Receptors, G-Protein-Coupled 0
Phenylalanine 47E5O17Y3R
RXFP3 protein, human 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

20242-20247

Auteurs

Ross A D Bathgate (RAD)

The Florey, The University of Melbourne, Parkville, VIC 3052, Australia.
Department of Biochemistry and Pharmacology, The University of Melbourne, Parkville, VIC 3052, Australia.

Praveen Praveen (P)

The Florey, The University of Melbourne, Parkville, VIC 3052, Australia.

Ashish Sethi (A)

Department of Biochemistry and Pharmacology, The University of Melbourne, Parkville, VIC 3052, Australia.
Australian Nuclear Science Technology Organisation, The Australian Synchrotron, Clayton, VIC 3168, Australia.

Werner I Furuya (WI)

The Florey, The University of Melbourne, Parkville, VIC 3052, Australia.

Rishi R Dhingra (RR)

The Florey, The University of Melbourne, Parkville, VIC 3052, Australia.
Florey Department of Neuroscience and Mental Health, The University of Melbourne, Parkville, VIC 3052, Australia.

Martina Kocan (M)

The Florey, The University of Melbourne, Parkville, VIC 3052, Australia.

Qinghao Ou (Q)

The Florey, The University of Melbourne, Parkville, VIC 3052, Australia.
ORCID: 0000-0002-0701-5323

Adam L Valkovic (AL)

The Florey, The University of Melbourne, Parkville, VIC 3052, Australia.

Isis Gil-Miravet (I)

Predepartmental Unit of Medicine, Faculty of Health Sciences, Universitat Jaume I, Avenida de Vicent Sos Baynat, s/n, 12071 Castelló de La Plana, Spain.

Mónica Navarro-Sánchez (M)

Predepartmental Unit of Medicine, Faculty of Health Sciences, Universitat Jaume I, Avenida de Vicent Sos Baynat, s/n, 12071 Castelló de La Plana, Spain.

Francisco E Olucha-Bordonau (FE)

Predepartmental Unit of Medicine, Faculty of Health Sciences, Universitat Jaume I, Avenida de Vicent Sos Baynat, s/n, 12071 Castelló de La Plana, Spain.

Andrew L Gundlach (AL)

The Florey, The University of Melbourne, Parkville, VIC 3052, Australia.
Florey Department of Neuroscience and Mental Health, The University of Melbourne, Parkville, VIC 3052, Australia.
Department of Anatomy and Physiology, The University of Melbourne, Parkville, VIC 3052, Australia.

K Johan Rosengren (KJ)

School of Biomedical Sciences, The University of Queensland, St Lucia, QLD 4072, Australia.
ORCID: 0000-0002-5007-8434

Paul R Gooley (PR)

Department of Biochemistry and Pharmacology, The University of Melbourne, Parkville, VIC 3052, Australia.
Bio21 Molecular Science and Biotechnology, The University of Melbourne, Parkville, VIC 3052, Australia.
ORCID: 0000-0002-0323-449X

Mathias Dutschmann (M)

The Florey, The University of Melbourne, Parkville, VIC 3052, Australia.
Florey Department of Neuroscience and Mental Health, The University of Melbourne, Parkville, VIC 3052, Australia.

Mohammed Akhter Hossain (MA)

The Florey, The University of Melbourne, Parkville, VIC 3052, Australia.
Florey Department of Neuroscience and Mental Health, The University of Melbourne, Parkville, VIC 3052, Australia.
School of Chemistry, The University of Melbourne, Parkville, VIC 3052, Australia.
ORCID: 0000-0002-9961-0006

Articles similaires

[Redispensing of expensive oral anticancer medicines: a practical application].

Lisanne N van Merendonk, Kübra Akgöl, Bastiaan Nuijen
1.00
Humans Antineoplastic Agents Administration, Oral Drug Costs Counterfeit Drugs

Smoking Cessation and Incident Cardiovascular Disease.

Jun Hwan Cho, Seung Yong Shin, Hoseob Kim et al.
1.00
Humans Male Smoking Cessation Cardiovascular Diseases Female

Evaluation of Low-Value Services Across Major Medicare Advantage Insurers and Traditional Medicare.

Ciara Duggan, Adam L Beckman, Ishani Ganguli et al.
1.00
Humans United States Aged Cross-Sectional Studies Medicare Part C

Effectiveness of Virtual Yoga for Chronic Low Back Pain: A Randomized Clinical Trial.

Hallie Tankha, Devyn Gaskins, Amanda Shallcross et al.
1.00
Humans Yoga Low Back Pain Female Male

Classifications MeSH

questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Primates › Haplorhini › Catarrhini › Hominidae › Humains › Noncovalent Peptide Stapling Using...
questionsmedicales.fr › Acides aminés, peptides et protéines › Peptides › Hormones peptidiques › Relaxine › Noncovalent Peptide Stapling Using...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Mécanismes moléculaires de l'action pharmacologique › Peptidomimétiques › Noncovalent Peptide Stapling Using...
questionsmedicales.fr › Acides aminés, peptides et protéines › Protéines › Protéines membranaires › Récepteurs de surface cellulaire › Récepteurs couplés aux protéines G › Noncovalent Peptide Stapling Using...
questionsmedicales.fr › Phénomènes chimiques › Phénomènes biochimiques › Conformation moléculaire › Conformation des protéines › Structure secondaire des protéines › Structure en hélice alpha › Noncovalent Peptide Stapling Using...
questionsmedicales.fr › Acides aminés, peptides et protéines › Acides aminés › Acides aminés essentiels › Phénylalanine › Noncovalent Peptide Stapling Using...