A hyperstable collagen mimic.

No abstract is available for this paper.

• Publication year

  1999

• Venue

  Chemistry and Biology

• Publication date

  1999-02-01

• Fields of study

  Medicine, Materials Science, Chemistry

• Identifiers
  DOI 10.1016/S1074-5521(99)80003-9PMID 10021421
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Inductive effects on the structure of proline residues.

  2009influential reference
• 2-Chlorotrityl chloride resin. Studies on anchoring of Fmoc-amino acids and peptide cleavage.

  2009cited by this paper
• Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids.

  2009cited by this paper
• ガーデニング完全ガイド : Practical handbook

  1999cited by this paper
• Collagen mimetics.

  1998cited by this paper
• Code for collagen's stability deciphered

  1998cited by this paper
• A thymidine triphosphate shape analog lacking Watson-Crick pairing ability is replicated with high sequence selectivity.

  1997cited by this paper
• Resonance in Formamide and Its Chalcogen Replacement Analogues: A Natural Population Analysis/Natural Resonance Theory Viewpoint

  1997cited by this paper
• Organic Fluorine Hardly Ever Accepts Hydrogen Bonds

  1997cited by this paper
• Some influences of fluorine in bioorganic chemistry

  1997cited by this paper
• Rotational Barriers of cis/trans Isomerization of Proline Analogues and Their Catalysis by Cyclophilin§

  1997cited by this paper
• The Energetics of Hydrogen Bonds in Model Systems: Implications for Enzymatic Catalysis

  1996cited by this paper
• Biomedical Frontiers of Fluorine Chemistry

  1996cited by this paper
• How good is fluorine as a hydrogen bond acceptor

  1996cited by this paper
• Inductive Effects on the Energetics of Prolyl Peptide Bond Isomerization: Implications for Collagen Folding and Stability.

  1996influential reference
• Grafting on nude mice of living skin equivalents produced using human collagens.

  1996cited by this paper
• Collagen-based biomaterials.

  1996cited by this paper
• Cell adhesion to collagenous matrices.

  1996cited by this paper
• Conformational Analysis of Molecules with Five-Membered Rings through NMR Determination of the Continuous Probability Distribution (CUPID) for Pseudorotation

  1996cited by this paper
• The collagen triple-helix: correlation of conformation with biological activities.

  1995cited by this paper
• The triple‐lielix motif in proteins

  1995cited by this paper
• The practice of peptide synthesis, 2nd ed., by M. Bodansky and A. Bodansky, Springer‐Verlag, New York. XVIII + 217 pp. price: $49.00

  1995cited by this paper
• Hydration structure of a collagen peptide.

  1995cited by this paper
• Intermolecular Effects in Crystals of 11-(Trifluoromethyl)-15,16-dihydrocyclopenta[a]phenanthren-17-one

  1994cited by this paper
• The Practice of Peptide Synthesis

  1994cited by this paper
• The conformation of 2-fluoroethanol — is intramolecular hydrogen bonding important?

  1994cited by this paper
• Crystal and molecular structure of a collagen-like peptide at 1.9 A resolution.

  1994influential reference
• How Does the 2'-Hydroxy Group Drive the Pseudorotational Equilibrium in Nucleoside and Nucleotide by the Tuning of the 3'-Gauche Effect?

  1994cited by this paper
• The geometry of intermolecular interactions in some crystalline fluorine-containing organic compounds

  1994cited by this paper
• Characterization of collagen-like peptides containing interruptions in the repeating Gly-X-Y sequence.

  1993cited by this paper
• Two-dimensional NMR assignments and conformation of (Pro-Hyp-Gly)10 and a designed collagen triple-helical peptide.

  1993cited by this paper
• Bioartificial polymeric materials: a new method to design biomaterials by using both biological and synthetic polymers

  1993cited by this paper
• Mutations in Collagen Genes as a Cause of Connective-Tissue Diseases

  1992cited by this paper
• Kinetics and thermodynamics of cis-trans isomerization of captopril and related compounds

  1992cited by this paper
• Seminars in medicine of the Beth Israel Hospital, Boston. Mutations in collagen genes as a cause of connective-tissue diseases.

  1992cited by this paper
• Study of the “molten globule” intermediate state in protein folding by a hydrophobic fluorescent probe

  1991cited by this paper
• Analysis of structural design features in collagen.

  1991cited by this paper
• Matrix metalloproteinases and their inhibitors in connective tissue remodeling

  1991cited by this paper
• The World of Peptides: A Brief History of Peptide Chemistry

  1991cited by this paper
• Practical Handbook of Biochemistry and Molecular Biology

  1989cited by this paper
• Protein stability curves

  1987cited by this paper
• Laser-induced alteration of collagen substructure allows microsurgical tissue welding.

  1986cited by this paper
• Hydrogen bonding and biological specificity analysed by protein engineering

  1985cited by this paper
• Peptide conformations. 20. Conformational analysis of proline rings from proton spin-spin coupling constants and force-field calculations: application to three cyclic tripeptides

  1983cited by this paper
• Intermolecular interactions of the carbon-fluorine bond: the crystallographic environment of fluorinated carboxylic acids and related structures

  1983cited by this paper
• Conformational implications of enzymatic proline hydroxylation in collagen.

  1982cited by this paper
• Anilinonaphthalene sulfonate as a probe of membrane composition and function.

  1982cited by this paper
• Crystal and molecular structure of a collagen-like polypeptide (Pro-Pro-Gly)10.

  1981cited by this paper
• Role of hydroxyproline in the stabilization of the collagen molecule via water molecules

  1980cited by this paper
• Nucleoside conformation is determined by the electronegativity of the sugar substituent.

  1980cited by this paper
• X-ray and NMR studies of L-4-hydroxyproline conformation in oligopeptides related to collagen

  1980cited by this paper
• Quantum-mechanical studies on the origin of barriers to internal rotation about single bonds

  1979cited by this paper
• CONFORMATIONS OF PROLINE

  1977cited by this paper
• The triple helix ⇌ coil conversion of collagen‐like polytripeptides in aqueous and nonaqueous solvents. Comparison of the thermodynamic parameters and the binding of water to (L‐Pro‐L‐Pro‐Gly)n and (L‐Pro‐L‐Hyp‐Gly)n

  1977cited by this paper
• Conformations of proline.

  1977cited by this paper
• The structure of water absorbed in collagen

  1976cited by this paper
• Conformations of glycyl-trans-4-fluoro-L-prolyl-L-tryptophan in aqueous solution.

  1976cited by this paper
• Information contained in the amino acid sequence of theα1(I)-chain of collagen and its consequences upon the formation of the triple helix, of fibrils and crosslinks

  1975cited by this paper
• Synthesis of (Pro-Hyp-Gly) n of defined molecular weights. Evidence for the stabilization of collagen triple helix by hydroxypyroline.

  1973cited by this paper
• Conformations of cis- and trans-4-fluoro-L-proline in aqueous solution.

  1973cited by this paper
• The thermal transition of a non-hydroxylated form of collagen. Evidence for a role for hydroxyproline in stabilizing the triple-helix of collagen.

  1973cited by this paper
• Gauche effect. Stereochemical consequences of adjacent electron pairs and polar bonds

  1972cited by this paper
• Fluorescence probes for structure.

  1972influential reference
• The origin of the inductive effect

  1972cited by this paper
• Thermal stability of tropocollagens--are hydrogen bonds really important?

  1971cited by this paper
• Characterization of the product formed by renaturation of alpha 1-CB2, a small peptide from collagen.

  1970cited by this paper
• Equilibrium and kinetic studies of the helix-coil transition in alpha 1-CB2, a small peptide from collagen.

  1970cited by this paper
• Biosynthesis of abnormal collagens with amino acid analogues. I. Incorporation of L-azetidine-2-carboxylic acid and cis-4-fluoro-L-proline into protocollagen and collagen.

  1969cited by this paper
• The hydration structure of collagen

  1969cited by this paper
• Biosynthesis of abnormal collagens with amino acid analogues. II. Inability of cartilage cells to extrude collagen polypeptides containing L-azetidine-2-carboxylic acid or cis-4-fluoro-L-proline.

  1969cited by this paper
• Strong Hydrogen Bonds. II. The Hydrogen Difluoride Ion

  1964cited by this paper
• Structures of Molecules and Crystals of Fluoro-Carbons

  1954cited by this paper
• The Nature Of The Chemical Bond

  1939cited by this paper
• Valence And The Structure Of Atoms And Molecules

  year unknowncited by this paper

• Molecular foundations of collagen triple helical assembly: the central role of prolyl-4-hydroxylation

  2026cites this paper
• Molecular versatility of polyproline II helices: from natural proteins to biomimetic materials.

  2026cites this paper
• A Malleable Collagen-Mimic that Undergoes Moisture-Induced Hardening for Gluing Hydrophilic Surfaces.

  2025cites this paper
• Water and Collagen: A Mystery Yet to Unfold

  2025cites this paper
• Decoding elegant interplay among different stereo-electronic effects due to the ancient prolyl-4-hydroxylation stabilizing collagenous helicity

  2025cites this paper
• Site-selective S-gem-difluoroallylation of unprotected peptides with 3,3-difluoroallyl sulfonium salts

  2024cites this paper
• Spatial polarimetric second harmonic generation evaluation of collagen in a hypophosphatasia mouse model

  2024cites this paper
• Late-stage gem-difluoroallylation of phenol in bioactive molecules and peptides with 3,3-difluoroallyl sulfonium salts

  2024cites this paper
• Investigating the effect of water on collagen triple helix stability

  2024cites this paper
• The Chemistry and Biology of Collagen Hybridization.

  2023cites this paper
• Hollow Octadecameric Self-Assembly of Collagen-like Peptides.

  2023cites this paper
• Design, Synthesis, and Photo-Responsive Properties of a Collagen Model Peptide Bearing an Azobenzene

  2022cites this paper
• A convenient synthetic route to (2S,4S)-methylproline and its exploration for protein engineering of thioredoxin.

  2022cites this paper
• Viscoelastic analysis of mussel threads reveals energy dissipative mechanisms

  2022cites this paper
• Fluorine-Containing Prolines: Synthetic Strategies, Applications, and Opportunities.

  2022cites this paper
• Temperature Distribution of Vessel Tissue by High Frequency Electric Welding with Combination Optical Measure and Simulation

  2022cites this paper
• Predicting the stability of homotrimeric and heterotrimeric collagen helices

  2021cites this paper
• Design, synthesis, and biochemical evaluation of alpha-amanitin derivatives containing analogs of the trans-hydroxyproline residue for potential use in antibody-drug conjugates.

  2021cites this paper
• Collagen- and hyaluronic acid-based hydrogels and their biomedical applications.

  2021cites this paper
• Toward Activatable Collagen Mimics: Combining DEPSI "Switch" Defects and Template-Guided Self-Organization to Control Collagen Mimetic Peptides.

  2021cites this paper
• Biomaterials via peptide assembly: design, characterization, and application in tissue engineering.

  2021cites this paper
• Fluorinated Rings: Conformation and Application.

  2021cites this paper
• Intersecting Xenobiology and Neometabolism To Bring Novel Chemistries to Life

  2020cites this paper
• Crystal structure of a ProM2 containing triple-helical collagen peptide.

  2020cites this paper
• Factors affecting thermal stability of collagen from the aspects of extraction, processing and modification

  2020cites this paper
• Cyclic Peptide Mimetic of Damaged Collagen

  2020cites this paper
• Recent trends in protein and peptide-based biomaterials for advanced drug delivery

  2020cites this paper
• Conformational landscape of substituted prolines

  2020cites this paper
• A solvation induced ring puckering effect in fluorinated prolines and its inclusion in classical force-fields

  2020cites this paper
• Triple‐Helix‐Stabilizing Effects in Collagen Model Peptides Containing PPII‐Helix‐Preorganized Diproline Modules

  2020cites this paper
• Using synthetic peptides and recombinant collagen to understand DDR-collagen interactions.

  2019cites this paper
• Synthesis and applications of backbone-fluorinated amino acids

  2019cites this paper
• A guide to high-efficiency chromium (III)-collagen cross-linking: Synchrotron SAXS and DSC study.

  2019cites this paper
• Bound Water and Hydroxyproline are the essential contributors to collagen molecular stability: A Computational Analysis

  2019cites this paper
• Current Trends in the Analysis of Post-translational Modifications

  2019cites this paper
• Modulating the collagen triple helix formation by switching: Positioning effects of depsi-defects on the assembly of [Gly-Pro-Pro]7 collagen mimetic peptides

  2019cites this paper
• Methods for the Construction of Collagen-Based Triple-Helical Peptides Designed as Matrix Metalloproteinase Inhibitors.

  2019cites this paper
• Temperature-controlled electrospray ionization mass spectrometry as a tool to study collagen homo- and heterotrimers

  2019cites this paper
• The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research

  2018cites this paper
• Collagen degradation in tuberculosis pathogenesis: the biochemical consequences of hosting an undesired guest.

  2018cites this paper
• The Collagen Suprafamily: From Biosynthesis to Advanced Biomaterial Development

  2018cites this paper
• Moisture-triggered actuator and detector with high-performance: interface engineering of graphene oxide/ethyl cellulose

  2018cites this paper
• Cross-Linked Collagen Triple Helices by Oxime Ligation.

  2017cites this paper
• 4-Fluoroprolines: Conformational Analysis and Effects on the Stability and Folding of Peptides and Proteins.

  2017cites this paper
• Method Dependence of Proline Ring Flexibility in the Poly-l-Proline Type II Polymer.

  2017cites this paper
• Akkaretal. (2004) “Solubilizing Poorly Soluble Antimycotic Agents by Emulsification Via a Solvent-Free Process.” AAPS PharmSciTech 5(1). Ashok et al. (2004) “In Vitro Characterization of PEGylated Phospholipid Micelles for Improved Drug Solubilization: Effects of PEG Chain Length and PC Incorporatio

  2017cites this paper
• Production of recombinant collagen: state of the art and challenges

  2017cites this paper
• Effect of N- and C-terminal functional groups on the stability of collagen triple helices.

  2017cites this paper
• Second Generation Triple-Helical Peptide Inhibitors of Matrix Metalloproteinases.

  2017cites this paper
• Peptidyl-Prolyl Model Study: How Does the Electronic Effect Influence the Amide Bond Conformation?

  2017cites this paper
• Collagen-Like Peptide Bioconjugates.

  2017cites this paper
• Future Prospects for Scaffolding Methods and Biomaterials in Skin Tissue Engineering: A Review

  2016cites this paper
• Collagen structure: new tricks from a very old dog.

  2016cites this paper
• A Single Stereodynamic Center Modulates the Rate of Self-Assembly in a Biomolecular System.

  2015cites this paper
• Peptide‐Based Inhibitors of Enzymes

  2015cites this paper
• Biomimetic Self-Templated Hierarchical Structures of Collagen-Like Peptide Amphiphiles.

  2015cites this paper
• In vivo studies of ultrafast near-infrared laser tissue bonding and wound healing

  2015cites this paper
• Advances in Skin Regeneration: Application of Electrospun Scaffolds

  2015cites this paper
• Elastomeric Materials, Protein-Based: Structure–Function Relationships

  2015cites this paper
• Fluorinated Amino Acids, Peptides, and Proteins

  2015cites this paper
• Proline Methanologues: Design, Synthesis, Structural Properties, and Applications in Medicinal Chemistry

  2015cites this paper
• Fluoro amino acids: A rarity in nature, yet a prospect for protein engineering

  2015cites this paper
• Investigation of cis- and trans-4-Fluoroprolines as Enantioselective Catalysts in a Variety of Organic Transformations

  2015cites this paper
• Metal Stabilization of Collagen and de Novo Designed Mimetic Peptides.

  2015cites this paper
• Structurally defined nanoscale sheets from self-assembly of collagen-mimetic peptides.

  2014cites this paper
• Handedness preference and switching of peptide helices. Part I: Helices based on protein amino acids

  2014cites this paper
• Native peptide folding dominates over stereoelectronic effects of prolyl hydroxylation in loop 5 of the macrocyclic peptide kalata B1

  2014cites this paper
• Development of a fluorescence resonance energy transfer assay for monitoring bacterial collagenase triple-helical peptidase activity

  2014cites this paper
• The Functional Role of Extracellular Matrix

  2014cites this paper
• Designing protein-based biomaterials for medical applications.

  2014cites this paper
• Structurally homogeneous nanosheets from self-assembly of a collagen-mimetic peptide.

  2014cites this paper
• Characterization of BcaA, a Putative Classical Autotransporter Protein in Burkholderia pseudomallei

  2013cites this paper
• Easy chairs: the conformational preferences of polyfluorocyclohexanes

  2013cites this paper
• Stabilization of collagen-model, triple-helical peptides for in vitro and in vivo applications.

  2013cites this paper
• Peptide Modifications to Increase Metabolic Stability and Activity

  2013cites this paper
• Collagen-like peptides and peptide-polymer conjugates in the design of assembled materials.

  2013cites this paper
• (4R)‐ and (4S)‐Fluoroproline in the Conserved cis‐Prolyl Peptide Bond of the Thioredoxin Fold: Tertiary Structure Context Dictates Ring Puckering

  2013cites this paper
• Pharmaceuticals and Other Biomedical Applications

  2013cites this paper
• From azidoproline to functionalizable collagen.

  2013cites this paper
• Recombinant protein polymers in biomaterials.

  2013cites this paper
• Stereoselectively fluorinated N-heterocycles: a brief survey

  2013cites this paper
• Conformational stability of collagen triple helices functionalized in the Yaa position by click chemistry.

  2012cites this paper
• Organic fluorine as a polypeptide building element: in vivo expression of fluorinated peptides, proteins and proteomes.

  2012cites this paper
• Congeneric bio-adhesive mussel foot proteins designed by modified prolines revealed a chiral bias in unnatural translation.

  2012cites this paper
• 4(R/S)-Amino/guanidino-substituted proline peptides: design, synthesis and DNA transfection properties.

  2012cites this paper
• Effect of sterically demanding substituents on the conformational stability of the collagen triple helix.

  2012cites this paper
• Growth factor delivery: how surface interactions modulate release in vitro and in vivo.

  2012cites this paper
• Synthesis and conformation of fluorinated β-peptidic compounds.

  2012cites this paper
• Collagen scaffolds derived from fresh water fish origin and their biocompatibility.

  2012cites this paper
• Fluorinated amino acids: compatibility with native protein structures and effects on protein-protein interactions.

  2012cites this paper
• Synthesis of 3-fluoropyrrolidines and 4-fluoropyrrolidin-2-ones from allylic fluorides.

  2012cites this paper
• Sequence position and side chain length dependence of charge pair interactions in collagen triple helices.

  2012cites this paper
• Peptides that anneal to natural collagen in vitro and ex vivo.

  2012cites this paper
• Three intrinsically unstructured mussel adhesive proteins, mfp‐1, mfp‐2, and mfp‐3: Analysis by circular dichroism

  2012cites this paper
• (2S,4R)-4-Fluoropyrrolidinium-2-carboxylate

  2012cites this paper
• 9.05 – Elastins

  2012cites this paper
• Conformational analysis of fluorinated pyrrolidines using 19F-1H scalar couplings and heteronuclear NOEs.

  2012cites this paper
• Solid phase synthesis of peptides containing backbone-fluorinated amino acids.

  2012cites this paper
• Positive and negative design leads to compositional control in AAB collagen heterotrimers.

  2011cites this paper
• Collagen Mimetic Peptides: Progress Towards Functional Applications.

  2011cites this paper