Amine-bearing hydrocarbon cross-links: Tailoring helix stability, hydrophilicity, and synthetic adaptability in peptides

Duc V.H. Tran; Thanh K. Pham; Young Woo Kim

doi:10.1016/j.bmc.2024.117893

Amine-bearing hydrocarbon cross-links: Tailoring helix stability, hydrophilicity, and synthetic adaptability in peptides

Duc V.H. Tran
, Thanh K. Pham
, Young Woo Kim

Department of Pharmacy

Dongguk University

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

This study comprehensively explored the helix-stabilizing effects of amine-bearing hydrocarbon cross-links (ABXs), revealing their context-dependent nature influenced by various structural parameters. Notably, we identified a 9-atom ABX as a robust helix stabilizer, showcasing versatile synthetic adaptability while preserving peptide water solubility. Future investigations are imperative to fully exploit this system's potential and enrich our chemical toolkit for designing innovative peptide-based biomolecules.

Original language	English
Article number	117893
Journal	Bioorganic and Medicinal Chemistry
Volume	112
DOIs	https://doi.org/10.1016/j.bmc.2024.117893
State	Published - 1 Oct 2024

Keywords

Amine cross-link
Peptide drugs
Peptide stapling
Ring-closing metathesis
α-Helix

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10.1016/j.bmc.2024.117893

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title = "Amine-bearing hydrocarbon cross-links: Tailoring helix stability, hydrophilicity, and synthetic adaptability in peptides",

abstract = "This study comprehensively explored the helix-stabilizing effects of amine-bearing hydrocarbon cross-links (ABXs), revealing their context-dependent nature influenced by various structural parameters. Notably, we identified a 9-atom ABX as a robust helix stabilizer, showcasing versatile synthetic adaptability while preserving peptide water solubility. Future investigations are imperative to fully exploit this system's potential and enrich our chemical toolkit for designing innovative peptide-based biomolecules.",

keywords = "Amine cross-link, Peptide drugs, Peptide stapling, Ring-closing metathesis, α-Helix",

author = "Tran, \{Duc V.H.\} and Pham, \{Thanh K.\} and Kim, \{Young Woo\}",

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AU - Kim, Young Woo

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KW - Amine cross-link

KW - Peptide drugs

KW - Peptide stapling

KW - Ring-closing metathesis

KW - α-Helix

UR - https://www.scopus.com/pages/publications/85202078298

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Amine-bearing hydrocarbon cross-links: Tailoring helix stability, hydrophilicity, and synthetic adaptability in peptides

Abstract

Keywords

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