4.6 Article

Introducing Aliphatic Fluoropeptides: Perspectives on Folding Properties, Membrane Partition and Proteolytic Stability

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Biochemistry & Molecular Biology

pH-induced insertion of pHLIP into a lipid bilayer: In-situ SEIRAS characterization of a folding intermediate at neutral pH

Kenichi Ataka et al.

Summary: The pH low insertion peptide (pHLIP) is a pH-sensitive cell penetrating peptide that undergoes conformational changes from a coil to an alpha-helix in response to pH. It has potential applications in drug delivery and visualization of acidic tissues. In this study, the pH-induced insertion and folding processes of pHLIP into a lipid bilayer were examined using surface-enhanced infrared absorption spectroscopy. The results showed that the peptide forms a partially helical structure at slightly acidic pH and undergoes further reorientation and insertion into the membrane at lower pH. The formation of alpha-helical structure and complete secondary structure occurs at pH 5.3. Analysis of the vibrational bands suggests the involvement of specific amino acid groups in the conformational changes of pHLIP in different pH states.

BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES (2022)

Article Chemistry, Organic

Gram-Scale Asymmetric Synthesis of Fluorinated Amino Acids Using a Chiral Nickel(II) Complex

Thomas Hohmann et al.

Summary: Fluorinated amino acids play an important role in peptide and protein engineering. However, strategies for their synthesis have been poorly described, and a uniform approach using similar starting materials is needed. This study presents a strategy based on chiral Ni(II) complexes to synthesize enantiopure fluorinated amino acids on a gram-scale. The hydrophobicity and alpha-helix propensity of the synthesized fluorinated amino acids were also characterized.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Review Biotechnology & Applied Microbiology

Strategies employed in the design of antimicrobial peptides with enhanced proteolytic stability

Zhenheng Lai et al.

Summary: Due to the fast development of multidrug-resistant bacterial pathogens, the development and modification of antimicrobial peptides (AMPs) are highly active. However, the clinical translation of peptide antibiotics is still inadequate despite considerable efforts. Improving the proteolytic stability of AMPs is crucial and various design strategies have been explored.

BIOTECHNOLOGY ADVANCES (2022)

Article Chemistry, Multidisciplinary

Highly Fluorinated Peptide Probes with Enhanced In Vivo Stability for 19F-MRI

Beibei Meng et al.

Summary: A labeling strategy for in vivo F-19-MRI based on highly fluorinated, short hydrophilic peptide probes, is developed. These probes are functionalized further by a fluorophore and an alkyne moiety for bioconjugation. The design of the peptide probes ensures low cytotoxicity and high serum stability. The performance of these probes in F-19-MRI is demonstrated and they are found to exhibit high stability and long circulation times in living zebrafish embryos. Overall, these peptide probes are suitable for in vivo F-19-MRI applications.
Article Biochemistry & Molecular Biology

Fluorine-induced polarity increases inhibitory activity of BPTI towards chymotrypsin

Jakob Leppkes et al.

Summary: This study systematically investigated the site-specific incorporation of non-canonical amino acids into BPTI using microwave-assisted solid-phase peptide synthesis. It was found that fluorinated BPTI showed enhanced inhibitory activity towards serine protease, and the complex structures were further analyzed using X-ray analysis. These findings highlight the potential of fluorine as a tool in protein engineering to beneficially alter protein-protein interactions.

RSC CHEMICAL BIOLOGY (2022)

Article Chemistry, Physical

Remarkably high solvatochromism in the circular dichroism spectra of the polyproline-II conformation: limitations or new opportunities?

Vladimir Kubyshkin et al.

Summary: Circular dichroism is a conventional method for studying the secondary structures of peptides and proteins. The polyproline-II helix, while not exhibiting strictly conserved spectroscopic appearance, is significantly influenced by the surrounding solvent environment. Changes in solvation can lead to shifts and variations in the circular dichroism spectra, with new features potentially emerging in nonpolar environments. Additionally, the transition to a transmembrane state in isotropic liposomes is correlated with specific spectral changes, indicating the importance of considering the solvent environment in assessing circular dichroism spectra.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2021)

Review Chemistry, Multidisciplinary

Fluoropolymers in biomedical applications: state-of-the-art and future perspectives

Jia Lv et al.

Summary: Fluoropolymers possess unique physicochemical properties and have been widely used in biomedical applications, especially in gene delivery, drug delivery, magnetic resonance imaging, etc. They exhibit distinct mechanisms and features in these specific applications, but also face challenges in utilizing their full potential in the biomedical field.

CHEMICAL SOCIETY REVIEWS (2021)

Article Chemistry, Inorganic & Nuclear

Improved enantioselective gram scale synthesis route to N-Fmoc-protected monofluoroethylglycine

Jakob Leppkes et al.

JOURNAL OF FLUORINE CHEMISTRY (2020)

Article Multidisciplinary Sciences

Fluoroalkylation promotes cytosolic peptide delivery

Guangyu Rong et al.

SCIENCE ADVANCES (2020)

Review Chemistry, Inorganic & Nuclear

Next generation organofluorine containing blockbuster drugs

Jianlin Han et al.

JOURNAL OF FLUORINE CHEMISTRY (2020)

Article Biochemistry & Molecular Biology

Lipid membrane interactions of a fluorinated peptide with potential ion channel- forming ability

Maud Auger et al.

PEPTIDE SCIENCE (2019)

Article Chemistry, Multidisciplinary

Perfluoroaryl Bicyclic Cell-Penetrating Peptides for Delivery of Antisense Oligonucleotides

Justin M. Wolfe et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Review Chemistry, Organic

Fine-Tuning the Proteolytic Stability of Peptides with Fluorinated Amino Acids

Susanne Huhmann et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Physical

Transmembrane Polyproline Helix

Vladimir Kubyshkin et al.

JOURNAL OF PHYSICAL CHEMISTRY LETTERS (2018)

Article Multidisciplinary Sciences

The fluorination effect of fluoroamphiphiles in cytosolic protein delivery

Zhenjing Zhang et al.

NATURE COMMUNICATIONS (2018)

Article Multidisciplinary Sciences

Structure formation during translocon-unassisted co-translational membrane protein folding

Nicola J. Harris et al.

SCIENTIFIC REPORTS (2017)

Review Chemistry, Multidisciplinary

Deciphering the Fluorine Code-The Many Hats Fluorine Wears in a Protein Environment

Allison Ann Berger et al.

ACCOUNTS OF CHEMICAL RESEARCH (2017)

Review Chemistry, Multidisciplinary

The road to the synthesis of difficult peptides

Marta Paradis-Bas et al.

CHEMICAL SOCIETY REVIEWS (2016)

Article Multidisciplinary Sciences

In-Situ Observation of Membrane Protein Folding during Cell-Free Expression

Axel Baumann et al.

PLOS ONE (2016)

Article Multidisciplinary Sciences

Membrane Assembly and Ion Transport Ability of a Fluorinated Nanopore

Raphael Godbout et al.

PLOS ONE (2016)

Review Biochemistry & Molecular Biology

Surface-enhanced infrared absorption spectroscopy (SEIRAS) to probe monolayers of membrane proteins

Kenichi Ataka et al.

BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES (2013)

Review Biochemistry & Molecular Biology

Polyproline-II Helix in Proteins: Structure and Function

Alexei A. Adzhubei et al.

JOURNAL OF MOLECULAR BIOLOGY (2013)

Article Environmental Sciences

Toxicology of perfluorinated compounds

Thorsten Stahl et al.

Environmental Sciences Europe (2011)

Review Chemistry, Multidisciplinary

Thinner, Smaller, Faster: IR Techniques To Probe the Functionality of Biological and Biomimetic Systems

Kenichi Ataka et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Review Biochemistry & Molecular Biology

Fluorine-a new element in the design of membrane-active peptides

E. Neil G. Marsh et al.

MOLECULAR BIOSYSTEMS (2009)

Article Chemistry, Multidisciplinary

Antimicrobial activity and protease stability of peptides containing fluorinated amino acids

He Meng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Multidisciplinary

Aggregation of the amphipathic peptides (AAKA)n into antiparallel, β-sheets

Thomas J. Measey et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Review Chemistry, Multidisciplinary

Conformation of the backbone in unfolded proteins

Zhengshuang Shi et al.

CHEMICAL REVIEWS (2006)

Article Chemistry, Multidisciplinary

Fluorinated interfaces drive self-association of transmembrane alpha helices in lipid bilayers

N Naarmann et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

Article Chemistry, Multidisciplinary

Fluorine in a native protein environment - How the spatial demand and polarity of fluoroalkyl groups affect protein folding

Christian Jaeckel et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

Article Chemistry, Organic

Advanced approaches for the characterization of a de novo designed antiparallel coiled coil peptide

K Pagel et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2005)

Article Chemistry, Multidisciplinary

Solvent dependence of PII conformation in model alanine peptides

ZG Liu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

Article Multidisciplinary Sciences

De novo design of defined helical bundles in membrane environments

B Bilgiçer et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2004)

Review Biochemistry & Molecular Biology

Fluorine in medicinal chemistry

HJ Böhm et al.

CHEMBIOCHEM (2004)

Article Chemistry, Multidisciplinary

Stable conformations of tripeptides in aqueous solution studied by UV circular dichroism spectroscopy

F Eker et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2003)

Review Chemistry, Multidisciplinary

Serine protease mechanism and specificity

L Hedstrom

CHEMICAL REVIEWS (2002)

Article Multidisciplinary Sciences

Polyproline II structure in a sequence of seven alanine residues

ZS Shi et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2002)

Correction Biochemistry & Molecular Biology

Free energies of protein decoys provide insight into determinants of protein stability (vol 10, pg 2498, 2001)

YN Vorobjev et al.

PROTEIN SCIENCE (2002)

Article Biochemistry & Molecular Biology

Polyproline II helical structure in protein unfolded states: Lysine peptides revisited

AL Rucker et al.

PROTEIN SCIENCE (2002)

Review Pharmacology & Pharmacy

Fluorocarbons and fluorinated amphiphiles in drug delivery and biomedical research

MP Krafft

ADVANCED DRUG DELIVERY REVIEWS (2001)