Water-Based Dynamic Depsipeptide Chemistry: Building Block Recycling and Oligomer Distribution Control Using Hydration-Dehydration Cycles.


Journal

JACS Au
ISSN: 2691-3704
Titre abrégé: JACS Au
Pays: United States
ID NLM: 101775714

Informations de publication

Date de publication:
27 Jun 2022
Historique:
received: 11 02 2022
revised: 31 03 2022
accepted: 27 04 2022
entrez: 5 7 2022
pubmed: 6 7 2022
medline: 6 7 2022
Statut: epublish

Résumé

The high kinetic barrier to amide bond formation has historically placed narrow constraints on its utility in reversible chemistry applications. Slow kinetics has limited the use of amides for the generation of diverse combinatorial libraries and selection of target molecules. Current strategies for peptide-based dynamic chemistries require the use of nonpolar co-solvents or catalysts or the incorporation of functional groups that facilitate dynamic chemistry between peptides. In light of these limitations, we explored the use of depsipeptides: biorelevant copolymers of amino and hydroxy acids that would circumvent the challenges associated with dynamic peptide chemistry. Here, we describe a model system of

Identifiants

pubmed: 35783166
doi: 10.1021/jacsau.2c00087
pmc: PMC9241005
doi:

Types de publication

Journal Article

Langues

eng

Pagination

1395-1404

Informations de copyright

© 2022 The Authors. Published by American Chemical Society.

Déclaration de conflit d'intérêts

The authors declare no competing financial interest.

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Auteurs

Martin C (M)

School of Chemistry & Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.
NSF/NASA Center for Chemical Evolution, Atlanta, Georgia 30332, United States.

Moran Frenkel-Pinter (M)

School of Chemistry & Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.
NSF/NASA Center for Chemical Evolution, Atlanta, Georgia 30332, United States.

Kelvin H Smith (KH)

NSF/NASA Center for Chemical Evolution, Atlanta, Georgia 30332, United States.
School of Chemical & Biomolecular Engineering, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.

Victor F Rivera-Santana (VF)

Department of Chemistry, University of Puerto Rico, Mayagüez, Puerto Rico 00681, United States.

Alyssa B Sargon (AB)

NSF/NASA Center for Chemical Evolution, Atlanta, Georgia 30332, United States.
School of Chemical & Biomolecular Engineering, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.

Kaitlin C Jacobson (KC)

NSF/NASA Center for Chemical Evolution, Atlanta, Georgia 30332, United States.
School of Chemical & Biomolecular Engineering, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.

Aikomari Guzman-Martinez (A)

Department of Chemistry, University of Puerto Rico, Mayagüez, Puerto Rico 00681, United States.

Loren Dean Williams (LD)

NSF/NASA Center for Chemical Evolution, Atlanta, Georgia 30332, United States.
School of Chemistry & Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.

Luke J Leman (LJ)

NSF/NASA Center for Chemical Evolution, Atlanta, Georgia 30332, United States.
Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, United States.

Charles L Liotta (CL)

NSF/NASA Center for Chemical Evolution, Atlanta, Georgia 30332, United States.
School of Chemistry & Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.

Martha A Grover (MA)

NSF/NASA Center for Chemical Evolution, Atlanta, Georgia 30332, United States.
School of Chemical & Biomolecular Engineering, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.

Nicholas V Hud (NV)

NSF/NASA Center for Chemical Evolution, Atlanta, Georgia 30332, United States.
School of Chemistry & Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.

Classifications MeSH