(E)-alkene and ethylene isosteres substantially alter the hydrogen-bonding network in class II MHC A(q)/glycopeptide complexes and affect T-cell recognition.

No abstract is available for this paper.

• Publication year

  2011

• Venue

  Journal of the American Chemical Society

• Publication date

  2011-08-19

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/ja2038722PMID 21766871
• 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.

• Design of Glycopeptides Used to Investigate Class II MHC Binding and T-Cell Responses Associated with Autoimmune Arthritis

  2011cited by this paper
• Non-additivity of functional group contributions in protein-ligand binding: a comprehensive study by crystallography and isothermal titration calorimetry.

  2010cited by this paper
• Protein Flexibility and Conformational Entropy in Ligand Design Targeting the Carbohydrate Recognition Domain of Galectin-3

  2010cited by this paper
• A Comparative Approach Linking Molecular Dynamics of Altered Peptide Ligands and MHC with In Vivo Immune Responses

  2010cited by this paper
• Constraining binding hot spots: NMR and molecular dynamics simulations provide a structural explanation for enthalpy-entropy compensation in SH2-ligand binding.

  2010cited by this paper
• Modeling the Ternary Complex TCR-Vβ/CollagenII(261–273)/HLA-DR4 Associated with Rheumatoid Arthritis

  2010cited by this paper
• Enhancement of hydrophobic interactions and hydrogen bond strength by cooperativity: synthesis, modeling, and molecular dynamics simulations of a congeneric series of thrombin inhibitors.

  2010cited by this paper
• Oxazole-modified glycopeptides that target arthritis-associated class II MHC A(q) and DR4 proteins.

  2010cited by this paper
• Flexibility of the MHC class II peptide binding cleft in the bound, partially filled, and empty states: a molecular dynamics simulation study.

  2009cited by this paper
• Thermodynamic and structural effects of conformational constraints in protein-ligand interactions. Entropic paradoxy associated with ligand preorganization.

  2009cited by this paper
• 3-Layer-based analysis of peptide-MHC interaction: in silico prediction, peptide binding affinity and T cell activation in a relevant allergen-specific model.

  2009cited by this paper
• Toward an atomistic understanding of the immune synapse: large-scale molecular dynamics simulation of a membrane-embedded TCR-pMHC-CD4 complex.

  2008cited by this paper
• Synthesis of C13-C25 fragment of 24-demethylbafilomycin C(1) via diastereoselective aldol reactions of a ketone boron enolate as the key step.

  2007cited by this paper
• Synthesis of the ABC- and D-ring systems of the indole alkaloid ambiguine G.

  2007cited by this paper
• Identification of an altered peptide ligand based on the endogenously presented, rheumatoid arthritis-associated, human cartilage glycoprotein-39(263–275) epitope: an MHC anchor variant peptide for immune modulation

  2007cited by this paper
• Taking control of P1, P1' and double bond stereochemistry in the synthesis of Phe-Phe (E)-alkene amide isostere dipeptidomimetics.

  2007cited by this paper
• Probing molecular interactions within class II MHC Aq/glycopeptide/T-cell receptor complexes associated with collagen-induced arthritis.

  2007cited by this paper
• Side-chain and backbone amide bond requirements for glycopeptide stimulation of T-cells obtained in a mouse model for rheumatoid arthritis.

  2006cited by this paper
• Therapeutic Vaccination of Active Arthritis with a Glycosylated Collagen Type II Peptide in Complex with MHC Class II Molecules1

  2006cited by this paper
• Second-generation peptidomimetic inhibitors of antigen presentation effectively treat autoimmune diseases in HLA-DR-transgenic mouse models.

  2006cited by this paper
• E-olefin dipeptide isostere incorporation into a polypeptide backbone enables hydrogen bond perturbation: probing the requirements for Alzheimer's amyloidogenesis.

  2005cited by this paper
• Energetics and cooperativity of the hydrogen bonding and anchor interactions that bind peptides to MHC class II protein.

  2005cited by this paper
• Identification of the minimal glycopeptide core recognized by T cells in a model for rheumatoid arthritis.

  2005cited by this paper
• Stereoselective terminal functionalization of small peptides for catalytic asymmetric synthesis of unnatural peptides.

  2004cited by this paper
• Structure-based discovery of nonpeptidic small organic compounds to block the T cell response to myelin basic protein.

  2004cited by this paper
• Development of highly diastereo- and enantioselective direct asymmetric aldol reaction of a glycinate Schiff base with aldehydes catalyzed by chiral quaternary ammonium salts.

  2004cited by this paper
• Binding affinities of host-guest, protein-ligand, and protein-transition-state complexes.

  2003cited by this paper
• Binding interactions between peptides and proteins of the class II Major Histocompatibility Complex

  2002cited by this paper
• Predominant selection of T cells specific for the glycosylated collagen type II epitope (263–270) in humanized transgenic mice and in rheumatoid arthritis

  2002cited by this paper
• Major histocompatibility complex class II binding characteristics of peptoid-peptide hybrids.

  2002cited by this paper
• Glycosylation of type II collagen is of major importance for T cell tolerance and pathology in collagen‐induced arthritis

  2002cited by this paper
• Synthesis and enzyme inhibitory activities of novel peptide isosteres.

  2002cited by this paper
• Glycopeptide Specificity of Helper T Cells Obtained in Mouse Models for Rheumatoid Arthritis

  2002cited by this paper
• Structural and Functional Consequences of Altering a Peptide MHC Anchor Residue1

  2001cited by this paper
• Energetic asymmetry among hydrogen bonds in MHC class II⋅peptide complexes

  2001cited by this paper
• Utility of azapeptides as major histocompatibility complex class II protein ligands for T-cell activation.

  2001cited by this paper
• Peptide and peptide mimetic inhibitors of antigen presentation by HLA-DR class II MHC molecules. Design, structure-activity relationships, and X-ray crystal structures.

  2000cited by this paper
• Magnitude of structural changes of the T-cell receptor binding regions determine the strength of T-cell antagonism: molecular dynamics simulations of HLA-DR4 (DRB1*0405) complexed with analogue peptide.

  2000cited by this paper
• Cutting edge: a single, essential hydrogen bond controls the stability of peptide-MHC class II complexes.

  1999cited by this paper
• Design and Synthesis of a Competent Pyrrolinone−Peptide Hybrid Ligand for the Class II Major Histocompatibility Complex Protein HLA-DR1

  1999cited by this paper
• Preparation of a Diglycosylated Hydroxylysine Building Block Used in Solid-Phase Synthesis of a Glycopeptide from Type II Collagen.

  1999cited by this paper
• Pseudopeptide ligands for MHC II-restricted T cells.

  1998cited by this paper
• The structural basis of MHC control of collagen‐induced arthritis; binding of the immunodominant type II collagen 256 – 270 glycopeptide to H‐2Aq and H‐2Ap molecules

  1998cited by this paper
• Molecular dynamics simulations of HLA-DR4 (DRB1*0405) complexed with analogue peptide: conformational changes in the putative T-cell receptor binding regions.

  1998cited by this paper
• Molecular modeling of hen egg lysozyme HEL[52-61] peptide binding to I-Ak MHC class II molecule.

  1998cited by this paper
• Synthesis, Biological Activity and Molecular Modelling of the 53-54 Ketomethylene Analogue ofHEL(52-61) . .

  1998cited by this paper
• High- and low-potency ligands with similar affinities for the TCR: the importance of kinetics in TCR signaling.

  1998cited by this paper
• Epitope glycosylation plays a critical role for T cell recognition of type II collagen in collagen‐induced arthritis

  1998cited by this paper
• In vivo T helper cell response to retro-inverso peptidomimetics.

  1997cited by this paper
• Fine specificity of antigen binding to two class I major histocompatibility proteins (B*2705 and B*2703) differing in a single amino acid residue

  1997cited by this paper
• On the immunogenic properties of retro-inverso peptides. Total retro-inversion of T-cell epitopes causes a loss of binding to MHC II molecules.

  1997cited by this paper
• A TCR binds to antagonist ligands with lower affinities and faster dissociation rates than to agonists.

  1996cited by this paper
• Kinetic discrimination in T-cell activation.

  1996cited by this paper
• Substitution of peptide bond 53-54 of HEL(52-61) with an ethylene bond rather than reduced peptide bond is tolerated by an MHC-II restricted T cell.

  1996cited by this paper
• Identification of MHC class II and TCR binding residues in the type II collagen immunodominant determinant mediating collagen-induced arthritis.

  1996cited by this paper
• VMD: visual molecular dynamics.

  1996cited by this paper
• Kinetic proofreading in T-cell receptor signal transduction.

  1995cited by this paper
• Kinetics of T-cell receptor binding to peptide/I-Ek complexes: correlation of the dissociation rate with T-cell responsiveness.

  1994cited by this paper
• Crystal structure of the human class II MHC protein HLA-DR1 complexed with an influenza virus peptide

  1994cited by this paper
• Minimum structural requirements for peptide presentation by major histocompatibility complex class II molecules: implications in induction of autoimmunity.

  1994cited by this paper
• A single amino acid change in a myelin basic protein peptide confers the capacity to prevent rather than induce experimental autoimmune encephalomyelitis.

  1991cited by this paper
• A highly convergent total synthesis of the spiroacetal macrolide (+)-milbemycinβ1

  1989cited by this paper
• Acidities of glycine Schiff bases and alkylation of their conjugate bases

  1988cited by this paper
• Synthesis of drimane sesquiterpenes an intramolecular diels-alder approach

  1988cited by this paper
• Synthesis of optically active 10,11-dihydro-5h-dibenzo[a,d]cycloheptenes

  1987cited by this paper
• Preorganization—From Solvents to Spherands

  1986cited by this paper
• Synthesis of Analogues of GABA. XIV. Synthesis and Activity of Unsaturated Derivatives of 5-Aminopentanoic Acid (d-Aminovaleric Acid)

  1985cited by this paper

• Clonally expanded HSP-specific T cells contribute to glaucomatous neurodegeneration via the mTORC1 pathway.

  2026cites this paper
• Chemical synthesis and functional evaluation of glycopeptides and glycoproteins containing rare glycosyl amino acid linkages.

  2024cites this paper
• Glycoconjugates for Adjuvants and Self-Adjuvanting Vaccines

  2021cites this paper
• Recognition of Class II MHC Peptide Ligands That Contain β-Amino Acids

  2019cites this paper
• Syntheses and applications of enantiopure δ-amino acids and their precursors

  2018cites this paper
• Dynamics Determine Signaling in a Multicomponent System Associated with Rheumatoid Arthritis.

  2018cites this paper
• Design strategies for new drugs targeting multicomponent systems : focusing on class II MHC proteins and acetylcholinesterase

  2017cites this paper
• Residue dependent hydrogen-bonding preferences in orthanilic acid-based short peptide β-turn motifs

  2016cites this paper
• Mild Oxidative Cleavage of 9‐BBN‐Protected Amino Acid Derivatives

  2015cites this paper
• Collagenolytic Matrix Metalloproteinase Activities toward Peptomeric Triple-Helical Substrates.

  2015cites this paper
• Consequences of Periodic α-to-β3 Residue Replacement for Immunological Recognition of Peptide Epitopes

  2015cites this paper
• Hydroxyethylene isosteres introduced in type II collagen fragments substantially alter the structure and dynamics of class II MHC A(q)/glycopeptide complexes.

  2015cites this paper
• Synthesis and structure of oxetane containing tripeptide motifs.

  2014cites this paper
• Facile synthesis of 5-hydroxy-L-lysine from D-galactose as a chiral-precursor.

  2014cites this paper
• The Ant‐Pro Reverse‐Turn Motif. Structural Features and Conformational Characteristics

  2013cites this paper
• Functional and genetic analyses of the MHC and its impact on autoimmunity in the rat

  2013cites this paper
• An unusual conformational similarity of two peptide folds featuring sulfonamide and carboxamide on the backbone.

  2012cites this paper