4.8 Review

Fluorinated amino acids: compatibility with native protein structures and effects on protein-protein interactions

Related references

Note: Only part of the references are listed.
Review Chemistry, Multidisciplinary

Organic fluorine compounds: a great opportunity for enhanced materials properties

Ricarda Berger et al.

CHEMICAL SOCIETY REVIEWS (2011)

Article Biochemistry & Molecular Biology

Probing aromatic, hydrophobic, and steric effects on the self-assembly of an amyloid-beta fragment peptide

F. Timur Senguen et al.

MOLECULAR BIOSYSTEMS (2011)

Article Chemistry, Multidisciplinary

A Highly Active DNA Polymerase with a Fluorous Core

Bastian Holzberger et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Article Chemistry, Multidisciplinary

Highly Specific Heterodimerization Mediated by Quadrupole Interactions

Hong Zheng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Editorial Material Chemistry, Multidisciplinary

Introducing Quadrupole Interactions into the Peptide Design Toolkit

Hana Robson Marsden et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Article Biochemistry & Molecular Biology

Evidence That Histidine Protonation of Receptor-Bound Anthrax Protective Antigen Is a Trigger for Pore Formation

D. Shyamali Wimalasena et al.

BIOCHEMISTRY (2010)

Article Biochemistry & Molecular Biology

Site-Specific Incorporation of Fluorotyrosines into Proteins in Escherichia coli by Photochemical Disguise

Bryan J. Wilkins et al.

BIOCHEMISTRY (2010)

Article Biochemistry & Molecular Biology

Thermodynamic Consequences of Incorporating 4-Substituted Proline Derivatives into a Small Helical Protein

Tong-Yuan Zheng et al.

BIOCHEMISTRY (2010)

Review Biochemistry & Molecular Biology

Beyond the Canonical 20 Amino Acids: Expanding the Genetic Lexicon

Travis S. Young et al.

JOURNAL OF BIOLOGICAL CHEMISTRY (2010)

Article Chemistry, Multidisciplinary

Replacing 32 Proline Residues by a Noncanonical Amino Acid Results in a Highly Active DNA Polymerase

Bastian Holzberger et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Biochemistry & Molecular Biology

Residue-specific global fluorination of Candida antarctica lipase B in Pichia pastoris

Nediljko Budisa et al.

MOLECULAR BIOSYSTEMS (2010)

Article Chemistry, Organic

Crystal structure of the insect neuropeptide proctolin

Judith A. K. Howard et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2010)

Review Chemistry, Physical

Collagen-Based Biomaterials for Tissue Engineering Applications

Remi Parenteau-Bareil et al.

MATERIALS (2010)

Article Biochemical Research Methods

Direct and continuous assay for prolyl 4-hydroxylase

Kelly L. Gorres et al.

ANALYTICAL BIOCHEMISTRY (2009)

Review Biochemistry & Molecular Biology

Collagen Structure and Stability

Matthew D. Shoulders et al.

ANNUAL REVIEW OF BIOCHEMISTRY (2009)

Article Biochemistry & Molecular Biology

Fluorine substitutions in an antigenic peptide selectively modulate T-cell receptor binding in a minimally perturbing manner

Kurt H. Piepenbrink et al.

BIOCHEMICAL JOURNAL (2009)

Article Biochemistry & Molecular Biology

Engineering Protein Stability and Specificity Using Fluorous Amino Acids: The Importance of Packing Effects

Benjamin C. Buer et al.

BIOCHEMISTRY (2009)

Article Chemistry, Medicinal

Origin of the stability conferred upon collagen by fluorination

Matthew D. Shoulders et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2009)

Article Chemistry, Medicinal

Positional effects of monofluorinated phenylalanines on histone acetyltransferase stability and activity

Natalya Voloshchuk et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2009)

Review Biotechnology & Applied Microbiology

Incorporation of non-natural modules into proteins: structural features beyond the genetic code

Ulrich Arnold

BIOTECHNOLOGY LETTERS (2009)

Article Biochemistry & Molecular Biology

Effects of Fluorination on the Folding Kinetics of a Heterodimeric Coiled Coil

Mario Salwiczek et al.

CHEMBIOCHEM (2009)

Article Chemistry, Multidisciplinary

Position-Dependent Effects of Fluorinated Amino Acids on the Hydrophobic Core Formation of a Heterodimeric Coiled Coil

Mario Salwiczek et al.

CHEMISTRY-A EUROPEAN JOURNAL (2009)

Review Chemistry, Inorganic & Nuclear

19F NMR applications in chemical biology

Steven L. Cobb et al.

JOURNAL OF FLUORINE CHEMISTRY (2009)

Article Chemistry, Physical

Fluorine in Protein Environments: A QM and MD Study

Sergey A. Samsonov et al.

JOURNAL OF PHYSICAL CHEMISTRY B (2009)

Article Chemistry, Multidisciplinary

Probing the Coupling between Proton and Electron Transfer in Photosystem II Core Complexes Containing a 3-Fluorotyrosine

Fabrice Rappaport et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Chemistry, Multidisciplinary

Effect of Highly Fluorinated Amino Acids on Protein Stability at a Solvent-Exposed Position on an Internal Strand of Protein G B1 Domain

Hsien-Po Chiu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Chemistry, Multidisciplinary

Expanding the Fluorous Arsenal: Tetrafluorinated Phenylalanines for Protein Design

Hong Zheng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Biochemistry & Molecular Biology

Stereoelectronic effects on the transition barrier of polyproline conformational interconversion

Yi-Chun Chiang et al.

PROTEIN SCIENCE (2009)

Review Biochemistry & Molecular Biology

Molecular dynamics guided study of salt bridge length dependence in both fluorinated and non-fluorinated parallel dimeric coiled-coils

Scott S. Pendley et al.

PROTEINS-STRUCTURE FUNCTION AND BIOINFORMATICS (2009)

Review Chemistry, Multidisciplinary

Chemoselective Ligation and Modification Strategies for Peptides and Proteins

Christian P. R. Hackenberger et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

Review Biophysics

Protein design by directed evolution

Christian Jaeckel et al.

ANNUAL REVIEW OF BIOPHYSICS (2008)

Article Biochemistry & Molecular Biology

Conformational preferences of substrates for human prolyl 4-hydroxylase

Kelly L. Gorres et al.

BIOCHEMISTRY (2008)

Article Biochemistry & Molecular Biology

The fluorous effect in proteins:: Properties of α4F6, a 4-α-helix bundle protein with a fluorocarbon core

Lindsey M. Gottler et al.

BIOCHEMISTRY (2008)

Article Biophysics

Singlet oxygen photosensitization by EGFP and its chromophore HBDI

Ana Jimenez-Banzo et al.

BIOPHYSICAL JOURNAL (2008)

Article Biochemistry & Molecular Biology

Using fluorous amino acids to modulate the biological activity of an antimicrobial peptide

Lindsey M. Gottler et al.

CHEMBIOCHEM (2008)

Review Chemistry, Multidisciplinary

Synthetic strategies to alpha-trifluoromethyl and alpha-difluoromethyl substituted alpha-amino acids

Rene Smits et al.

CHEMICAL SOCIETY REVIEWS (2008)

Review Chemistry, Multidisciplinary

Understanding organofluorine chemistry. An introduction to the C-F bond

David O'Hagan

CHEMICAL SOCIETY REVIEWS (2008)

Review Chemistry, Multidisciplinary

Fluorine in medicinal chemistry

Sophie Purser et al.

CHEMICAL SOCIETY REVIEWS (2008)

Article Chemistry, Inorganic & Nuclear

Incorporation of fluoroprolines to proctolin: Study on the effect of a fluorine atom toward peptidic conformation

Takamasa Kitamoto et al.

JOURNAL OF FLUORINE CHEMISTRY (2008)

Review Materials Science, Multidisciplinary

Peptide-based biopolymers in biomedicine and biotechnology

Dominic Chow et al.

MATERIALS SCIENCE & ENGINEERING R-REPORTS (2008)

Article Multidisciplinary Sciences

Synthetic Biology of Proteins: Tuning GFPs Folding and Stability with Fluoroproline

Thomas Steiner et al.

PLOS ONE (2008)

Article Multidisciplinary Sciences

Non-Natural and Photo-Reactive Amino Acids as Biochemical Probes of Immune Function

Marta Gomez-Nunez et al.

PLOS ONE (2008)

Article Multidisciplinary Sciences

Thrombogenic collagen-mimetic peptides: Self-assembly of triple helix-based fibrils driven by hydrophobic interactions

Mabel A. Cejas et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2008)

Article Biochemistry & Molecular Biology

Red fluorescent protein variants with incorporated non-natural amino acid analogues

Ann Goulding et al.

PROTEIN ENGINEERING DESIGN & SELECTION (2008)

Article Chemistry, Organic

Preparation and conformational study of CF3-containing enkephalin-derived oligopeptide

Takamasa Kitamoto et al.

TETRAHEDRON (2008)

Article Biochemistry & Molecular Biology

Effect of 2-fluorohistidine labeling of the anthrax protective antigen on stability, pore formation, and translocation

D. Shyamali Wimalasena et al.

BIOCHEMISTRY (2007)

Article Chemistry, Organic

Chemoenzymatic Synthesis of (S)-Hexafluoroleucine and (S)-Tetrafluoroleucine

Hsien-Po Chiu et al.

ORGANIC LETTERS (2007)

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 Multidisciplinary Sciences

An Expanded Set of Amino Acid Analogs for the Ribosomal Translation of Unnatural Peptides

Matthew C. T. Hartman et al.

PLOS ONE (2007)

Article Multidisciplinary Sciences

Evolution of a fluorinated green fluorescent protein

Tale Hyeon Yoo et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2007)

Article Biochemistry & Molecular Biology

A cation-π interaction discriminates among sodium channels that are either sensitive or resistant to tetrodotoxin block

Vincent P. Santarelli et al.

JOURNAL OF BIOLOGICAL CHEMISTRY (2007)

Article Biochemistry & Molecular Biology

Solution structure of a small protein containing a fluorinated side chain in the core

Gabriel Cornilescu et al.

PROTEIN SCIENCE (2007)

Review Chemistry, Multidisciplinary

20S proteasome and its inhibitors: Crystallographic knowledge for drug development

Ljudmila Borissenko et al.

CHEMICAL REVIEWS (2007)

Article Chemistry, Multidisciplinary

Stabilizing and destabilizing effects of phenylalanine→F5-phenylalanine mutations on the folding of a small protein

Matthew G. Woll et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Multidisciplinary

Helix propensity of highly fluorinated amino acids

Hsien-Po Chiu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Multidisciplinary

Reduction potential tuning of the blue copper center in Pseudomonas aeruginosa azurin by the axial methionine as probed by unnatural amino acids

Dewain K. Garner et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Multidisciplinary

Stereoelectronic tuning of the structure and stability of the trp cage miniprotein

Devan Naduthambi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Biotechnology & Applied Microbiology

Influence of global fluorination on chloramphenicol acetyltransferase activity and stability

Tatyana Panchenko et al.

BIOTECHNOLOGY AND BIOENGINEERING (2006)

Article Biochemistry & Molecular Biology

Stabilization of bzip peptides through incorporation of fluorinated aliphatic residues

Soojin Son et al.

CHEMBIOCHEM (2006)

Article Biochemistry & Molecular Biology

Effects of modification of the active site tyrosine of human DNA topoisomerase I

Rong Gao et al.

BIOCHEMISTRY (2006)

Article Biochemistry & Molecular Biology

4-Fluoroproline derivative peptides: effect on PPII conformation and SH3 affinity

Paolo Ruzza et al.

JOURNAL OF PEPTIDE SCIENCE (2006)

Article Biochemistry & Molecular Biology

Single proline residues can dictate the oxidative folding pathways of cysteine-rich peptides

C Boulegue et al.

JOURNAL OF MOLECULAR BIOLOGY (2006)

Article Multidisciplinary Sciences

Enzymatic aminoacylation of tRNA with unnatural amino acids

MCT Hartman et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2006)

Article Chemistry, Multidisciplinary

Electronic control of amide cis-trans isomerism via the aromatic-prolyl interaction

KM Thomas et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Multidisciplinary

Mono-, di-, tri-, and tetra-substituted fluorotyrosines: New probes for enzymes that use tyrosyl radicals in catalysis

MR Seyedsayamdost et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (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)

Review Chemistry, Multidisciplinary

Biologically active molecules with a light switch

Guenter Mayer et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

Article Chemistry, Multidisciplinary

Evolving proteins of novel composition

Jin Kim Montclare et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2006)

Article Chemistry, Multidisciplinary

Fluoroproline flip-flop: Regiochemical reversal of a stereoelectronic effect on peptide and protein structures

Wookhyun Kim 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 Biochemistry & Molecular Biology

Stereoelectronic effects on polyproline conformation

JC Horng et al.

PROTEIN SCIENCE (2006)

Article Chemistry, Multidisciplinary

A stereoelectronic effect on turn formation due to proline substitution in elastin-mimetic polypeptides

W Kim et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Article Chemistry, Multidisciplinary

Stereoelectronic and steric effects in the collagen triple helix: Toward a code for strand association

JA Hodges et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Article Multidisciplinary Sciences

High-resolution x-ray crystal structures of the villin headpiece subdomain, an ultrafast folding protein

TK Chiu et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2005)

Review Chemistry, Physical

Solid state 19F NMR methods for studying biomembranes

AS Ulrich

PROGRESS IN NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY (2005)

Article Chemistry, Multidisciplinary

Analogues of vaccinia virus DNA topoisomerase I modified at the active site tyrosine

R Gao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Review Chemistry, Multidisciplinary

Orthogonal multipolar interactions in structural chemistry and biology

R Paulini et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

Review Biotechnology & Applied Microbiology

The molecular properties and applications of Anthozoa fluorescent proteins and chromoproteins

VV Verkhusha et al.

NATURE BIOTECHNOLOGY (2004)

Article Chemistry, Multidisciplinary

Imino acids and collagen triple helix stability: Characterization of collagen-like polypeptides containing Hyp-Hyp-Gly sequence repeats

R Berisio et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

Article Chemistry, Organic

β,β-difluoro analogs of α-oxo-β-phenylpropionic acid and phenylalanine

M Schlosser et al.

TETRAHEDRON (2004)

Review Chemistry, Organic

Synthesis of fluorinated amino acids

XL Qiu et al.

TETRAHEDRON (2004)

Article Biochemistry & Molecular Biology

Aromatic interactions in peptides: Impact on structure and function

ML Waters

BIOPOLYMERS (2004)

Article Biochemical Research Methods

Site- and subunit-specific incorporation of unnatural amino acids into HIV-1 reverse transcriptase

GJ Klarmann et al.

PROTEIN EXPRESSION AND PURIFICATION (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)

Article Biochemistry & Molecular Biology

Evaluation of the molecular interactions of fluorinated amino acids with native polypepticles

C Jäckel et al.

CHEMBIOCHEM (2004)

Article Chemistry, Multidisciplinary

UCSF chimera - A visualization system for exploratory research and analysis

EF Pettersen et al.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2004)

Article Chemistry, Multidisciplinary

Triple-helix propensity of hydroxyproline and fluoroproline: Comparison of host-guest and repeating tripeptide collagen models

AV Persikov et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2003)

Article Chemistry, Multidisciplinary

2,3-difluorotyrosine at position 356 of ribonucleotide reductase R2: A probe of long-range proton-coupled electron transfer

CS Yee et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2003)

Article Biochemistry & Molecular Biology

Stereospecific interactions of proline residues in protein structures and complexes

R Bhattacharyya et al.

JOURNAL OF MOLECULAR BIOLOGY (2003)

Article Chemistry, Multidisciplinary

Stereoelectronic effects on collagen stability: The dichotomy of 4-fluoroproline diastereomers

JA Hodges et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2003)

Article Chemistry, Multidisciplinary

Incorporation of trifluoroisoleucine into proteins in vivo

P Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2003)

Article Biochemistry & Molecular Biology

Stabilization mechanism of triple helical structure of collagen molecules

Y Nishi et al.

LETTERS IN PEPTIDE SCIENCE (2003)

Article Chemistry, Inorganic & Nuclear

The C-F bond as a tool in the conformational control of amides

CRS Briggs et al.

JOURNAL OF FLUORINE CHEMISTRY (2003)

Review Biochemistry & Molecular Biology

Aromatic interactions in model systems

ML Waters

CURRENT OPINION IN CHEMICAL BIOLOGY (2002)

Article Multidisciplinary Sciences

Mechanism by which 2,2,2-trifluoroethanol/water mixtures stabilize secondary-structure formation in peptides: A molecular dynamics study

D Roccatano et al.

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

Article Chemistry, Multidisciplinary

Contribution of aromatic interactions to α-helix stability

SM Butterfield et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)

Review Pharmacology & Pharmacy

Cation-π interactions in ligand recognition and catalysis

N Zacharias et al.

TRENDS IN PHARMACOLOGICAL SCIENCES (2002)

Article Biochemistry & Molecular Biology

Designing a 20-residue protein

JW Neidigh et al.

NATURE STRUCTURAL BIOLOGY (2002)

Article Chemistry, Organic

Synthesis and thermodynamic characterization of self-sorting coiled coils

B Bilgiçer et al.

TETRAHEDRON (2002)

Article Chemistry, Multidisciplinary

Programmed self-sorting of coiled coils with leucine and hexafluoroleucine cores

B Bilgiçer et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)

Article Chemistry, Multidisciplinary

Biosynthesis of a highly stable coiled-coil protein containing hexafluoroleucine in an engineered bacterial host

Y Tang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)

Article Chemistry, Multidisciplinary

Protein tyrosine kinase Csk-catalyzed phosphorylation of Src containing unnatural tyrosine analogues

DX Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)

Article Chemistry, Multidisciplinary

Self-association and membrane-binding behavior of melittins containing trifluoroleucine

A Niemz et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)

Article Chemistry, Multidisciplinary

A coiled coil with a fluorous core

B Bilgiçer et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)

Article Biochemistry & Molecular Biology

Stabilization of coiled-coil peptide domains by introduction of trifluoroleucine

Y Tang et al.

BIOCHEMISTRY (2001)

Article Chemistry, Multidisciplinary

Conformational stability of collagen relies on a stereoelectronic effect

LE Bretscher et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)

Article Biochemistry & Molecular Biology

Probing the catalytic mechanism of the insulin receptor kinase with a tetrafluorotyrosine-containing peptide substrate

AJ Ablooglu et al.

JOURNAL OF BIOLOGICAL CHEMISTRY (2000)

Article Biochemical Research Methods

Noninvasive tracing of recombinant proteins with fluorophenylalanine-fingers

C Minks et al.

ANALYTICAL BIOCHEMISTRY (2000)

Article Biochemistry & Molecular Biology

Towards the nonstick egg: designing fluorous proteins

ENG Marsh

CHEMISTRY & BIOLOGY (2000)

Review Biochemistry & Molecular Biology

Synthesis of fluorinated amino acids

A Sutherland et al.

NATURAL PRODUCT REPORTS (2000)