Optimized selective N-methylation of peptides on solid support.

PubWeight™: 1.18‹?› | Rank: Top 10%

🔗 View Article (PMID 16189816)

Published in J Pept Sci on March 01, 2006

Authors

Eric Biron1, Jayanta Chatterjee, Horst Kessler

Author Affiliations

1: Department Chemie, Lehrstuhl II für Organische Chemie, Technische Universität München, Germany.

Articles citing this

Peptidomimetics, a synthetic tool of drug discovery. Curr Opin Chem Biol (2008) 1.37

Multiple N-methylation of MT-II backbone amide bonds leads to melanocortin receptor subtype hMC1R selectivity: pharmacological and conformational studies. J Am Chem Soc (2010) 1.20

Novel analogues of the therapeutic complement inhibitor compstatin with significantly improved affinity and potency. Mol Immunol (2010) 1.18

Macrocyclic β-sheet peptides that inhibit the aggregation of a tau-protein-derived hexapeptide. J Am Chem Soc (2011) 1.10

Highly specific, bisubstrate-competitive Src inhibitors from DNA-templated macrocycles. Nat Chem Biol (2012) 0.90

Synthesis of N-methylated cyclic peptides. Nat Protoc (2012) 0.90

Structure-activity relationship and metabolic stability studies of backbone cyclization and N-methylation of melanocortin peptides. Biopolymers (2008) 0.89

Photochemically-activated probes of protein-protein interactions. Org Lett (2007) 0.87

Optimization of peptide-based inhibitors of prostate-specific antigen (PSA) as targeted imaging agents for prostate cancer. Bioorg Med Chem (2009) 0.85

Chaperone-like N-methyl peptide inhibitors of polyglutamine aggregation. Biochemistry (2010) 0.82

Kinetic mechanism of protein N-terminal methyltransferase 1. J Biol Chem (2015) 0.80

The synthesis of methylated, phosphorylated, and phosphonated 3'-aminoacyl-tRNA(Sec) mimics. Chemistry (2013) 0.80

Generation of Multiple Reporter Ions from a Single Isobaric Reagent Increases Multiplexing Capacity for Quantitative Proteomics. Anal Chem (2015) 0.78

Novel synthon for incorporating 1,3-dimethyl imidazolium group into molecular architecture. Tetrahedron Lett (2007) 0.78

A convenient approach to synthesizing peptide C-terminal N-alkyl amides. Biopolymers (2011) 0.75

Cyclic Dipeptide Shuttles as a Novel Skin Penetration Enhancement Approach: Preliminary Evaluation with Diclofenac. PLoS One (2016) 0.75

Deletion of Ac-NMePhe(1) from [NMePhe(1) ]arodyn under acidic conditions, part 1: effects of cleavage conditions and N-terminal functionality. Biopolymers (2011) 0.75

Articles by these authors

RGD modified polymers: biomaterials for stimulated cell adhesion and beyond. Biomaterials (2003) 5.34

Activation of integrin function by nanopatterned adhesive interfaces. Chemphyschem (2004) 4.66

Cell spreading and focal adhesion dynamics are regulated by spacing of integrin ligands. Biophys J (2007) 3.57

Noninvasive visualization of the activated alphavbeta3 integrin in cancer patients by positron emission tomography and [18F]Galacto-RGD. PLoS Med (2005) 3.12

The RETINOBLASTOMA-RELATED gene regulates stem cell maintenance in Arabidopsis roots. Cell (2005) 2.77

[18F]Galacto-RGD: synthesis, radiolabeling, metabolic stability, and radiation dose estimates. Bioconjug Chem (2004) 2.20

Two-step methodology for high-yield routine radiohalogenation of peptides: (18)F-labeled RGD and octreotide analogs. J Nucl Med (2004) 2.14

N-methylation of peptides: a new perspective in medicinal chemistry. Acc Chem Res (2008) 2.02

Positron emission tomography using [18F]Galacto-RGD identifies the level of integrin alpha(v)beta3 expression in man. Clin Cancer Res (2006) 1.96

Perspectives on NMR in drug discovery: a technique comes of age. Nat Rev Drug Discov (2008) 1.95

WT p53, but not tumor-derived mutants, bind to Bcl2 via the DNA binding domain and induce mitochondrial permeabilization. J Biol Chem (2006) 1.94

Lateral spacing of integrin ligands influences cell spreading and focal adhesion assembly. Eur J Cell Biol (2005) 1.93

An unfolded CH1 domain controls the assembly and secretion of IgG antibodies. Mol Cell (2009) 1.90

Cilengitide: the first anti-angiogenic small molecule drug candidate design, synthesis and clinical evaluation. Anticancer Agents Med Chem (2010) 1.87

The RGD motif in fibronectin is essential for development but dispensable for fibril assembly. J Cell Biol (2007) 1.81

Impact of order and disorder in RGD nanopatterns on cell adhesion. Nano Lett (2009) 1.75

Multimeric cyclic RGD peptides as potential tools for tumor targeting: solid-phase peptide synthesis and chemoselective oxime ligation. Chemistry (2003) 1.69

Asymmetric activation of the hsp90 dimer by its cochaperone aha1. Mol Cell (2010) 1.65

A conserved spider silk domain acts as a molecular switch that controls fibre assembly. Nature (2010) 1.65

The N-terminal domain of p53 is natively unfolded. J Mol Biol (2003) 1.62

Ligands for mapping alphavbeta3-integrin expression in vivo. Acc Chem Res (2009) 1.60

Impact of local versus global ligand density on cellular adhesion. Nano Lett (2011) 1.58

Improving oral bioavailability of peptides by multiple N-methylation: somatostatin analogues. Angew Chem Int Ed Engl (2008) 1.48

Carbohydrate-based mimetics in drug design: sugar amino acids and carbohydrate scaffolds. Chem Rev (2002) 1.46

Protein repellent properties of covalently attached PEG coatings on nanostructured SiO(2)-based interfaces. Biomaterials (2007) 1.44

Induction of cell polarization and migration by a gradient of nanoscale variations in adhesive ligand spacing. Nano Lett (2008) 1.43

PET Imaging of Integrin αVβ3 Expression. Theranostics (2011) 1.41

The architecture of functional modules in the Hsp90 co-chaperone Sti1/Hop. EMBO J (2012) 1.36

Nanomolar small molecule inhibitors for alphav(beta)6, alphav(beta)5, and alphav(beta)3 integrins. J Med Chem (2002) 1.31

PET imaging of CXCR4 receptors in cancer by a new optimized ligand. ChemMedChem (2011) 1.28

Imaging of integrin alpha(v)beta(3) expression in patients with malignant glioma by [18F] Galacto-RGD positron emission tomography. Neuro Oncol (2009) 1.27

Hsp90 is regulated by a switch point in the C-terminal domain. EMBO Rep (2009) 1.24

Assessment of alphavbeta3 integrin expression after myocardial infarction by positron emission tomography. Cardiovasc Res (2008) 1.21

Multiple N-methylation of MT-II backbone amide bonds leads to melanocortin receptor subtype hMC1R selectivity: pharmacological and conformational studies. J Am Chem Soc (2010) 1.20

NMR chemical shift perturbation study of the N-terminal domain of Hsp90 upon binding of ADP, AMP-PNP, geldanamycin, and radicicol. Chembiochem (2003) 1.20

Cooperativity in adhesion cluster formation during initial cell adhesion. Biophys J (2008) 1.18

The structures of integrins and integrin-ligand complexes: implications for drug design and signal transduction. Angew Chem Int Ed Engl (2002) 1.17

First (18)F-labeled tracer suitable for routine clinical imaging of sst receptor-expressing tumors using positron emission tomography. Clin Cancer Res (2004) 1.15

Tumor Targeting via Integrin Ligands. Front Oncol (2013) 1.15

Hsp12 is an intrinsically unstructured stress protein that folds upon membrane association and modulates membrane function. Mol Cell (2010) 1.14

PET of CXCR4 expression by a (68)Ga-labeled highly specific targeted contrast agent. J Nucl Med (2011) 1.13

Intrinsic inhibition of the Hsp90 ATPase activity. J Biol Chem (2006) 1.13

BclxL changes conformation upon binding to wild-type but not mutant p53 DNA binding domain. J Biol Chem (2009) 1.12

The effect of multiple N-methylation on intestinal permeability of cyclic hexapeptides. Mol Pharm (2011) 1.10

Transmembrane signal transduction of the alpha(IIb)beta(3) integrin. Protein Sci (2002) 1.10

In support of the BMRB. Nat Struct Mol Biol (2012) 1.09

p53--a natural cancer killer: structural insights and therapeutic concepts. Angew Chem Int Ed Engl (2006) 1.08

Cellular unbinding forces of initial adhesion processes on nanopatterned surfaces probed with magnetic tweezers. Nano Lett (2006) 1.08

A computational model of transmembrane integrin clustering. Structure (2004) 1.08

Telethonin deficiency is associated with maladaptation to biomechanical stress in the mammalian heart. Circ Res (2011) 1.07

Convenient synthesis of N-methylamino acids compatible with Fmoc solid-phase peptide synthesis. J Org Chem (2005) 1.07

Expression of callose synthase genes and its connection with Npr1 signaling pathway during pathogen infection. Planta (2008) 1.06

Structural analysis of the interaction between Hsp90 and the tumor suppressor protein p53. Nat Struct Mol Biol (2011) 1.05

Cell interactions with hierarchically structured nano-patterned adhesive surfaces. Soft Matter (2009) 1.05

Synthesis and stereochemical assignment of DNA spore photoproduct analogues. Chemistry (2006) 1.04

Synthesis of novel 1,4,7,10-tetraazacyclodecane-1,4,7,10-tetraacetic acid (DOTA) derivatives for chemoselective attachment to unprotected polyfunctionalized compounds. Chemistry (2007) 1.03

N-methylation of peptides and proteins: an important element for modulating biological functions. Angew Chem Int Ed Engl (2012) 1.03

Photoswitched cell adhesion on surfaces with RGD peptides. J Am Chem Soc (2005) 1.03

Mimicking cellular environments by nanostructured soft interfaces. Nano Lett (2007) 1.02

3-Substituted indolizine-1-carbonitrile derivatives as phosphatase inhibitors. Bioorg Med Chem Lett (2005) 1.02

Endometrial cancer. BMJ (2011) 1.02

Molecular targeting with peptides or peptide-polymer conjugates: just a question of size? J Nucl Med (2005) 1.02

Characterization of human saposins by NMR spectroscopy. Biochemistry (2006) 1.02

Programmed death ligand-1 over-expression correlates with malignancy and contributes to immune regulation in ovarian cancer. Cancer Immunol Immunother (2013) 1.01

Ovarian cancer cell proliferation and motility is induced by engagement of integrin alpha(v)beta3/Vitronectin interaction. Biol Chem (2003) 1.01

N-methylated cyclic pentaalanine peptides as template structures. J Am Chem Soc (2006) 1.01

Intestinal permeability of cyclic peptides: common key backbone motifs identified. J Am Chem Soc (2012) 1.00

Diffusion NMR spectroscopy: folding and aggregation of domains in p53. Chembiochem (2005) 1.00

FOSL1 controls the assembly of endothelial cells into capillary tubes by direct repression of αv and β3 integrin transcription. Mol Cell Biol (2013) 1.00

68Ga-NODAGA-RGD is a suitable substitute for (18)F-Galacto-RGD and can be produced with high specific activity in a cGMP/GRP compliant automated process. Nucl Med Biol (2012) 0.99

Design, synthesis, and functionalization of dimeric peptides targeting chemokine receptor CXCR4. J Med Chem (2011) 0.98

Solid-phase synthesis of 1,3-azole-based peptides and peptidomimetics. Org Lett (2006) 0.96

Design of selective peptidomimetic agonists for the human orphan receptor BRS-3. J Med Chem (2003) 0.96

Development and evaluation of peptidic ligands targeting tumour-associated urokinase plasminogen activator receptor (uPAR) for use in alpha-emitter therapy for disseminated ovarian cancer. Eur J Nucl Med Mol Imaging (2007) 0.96

Transcriptional regulation by antitermination. Interaction of RNA with NusB protein and NusB/NusE protein complex of Escherichia coli. J Mol Biol (2002) 0.96

Cooperative binding of p53 to DNA: regulation by protein-protein interactions through a double salt bridge. Angew Chem Int Ed Engl (2005) 0.96

The CLIP/CLAP-HSQC: pure absorptive spectra for the measurement of one-bond couplings. J Magn Reson (2008) 0.95

Evidence for hetero-association of transmembrane helices of integrins. FEBS Lett (2004) 0.95

Polymeric substrates with tunable elasticity and nanoscopically controlled biomolecule presentation. Langmuir (2010) 0.95

NMR studies on the substrate-binding domains of the thermosome: structural plasticity in the protrusion region. J Mol Biol (2004) 0.94

Comparison of cyclic RGD peptides for αvβ3 integrin detection in a rat model of myocardial infarction. EJNMMI Res (2013) 0.94

Design and chemical synthesis of integrin ligands. Methods Enzymol (2007) 0.94

Titanium implant materials with improved biocompatibility through coating with phosphonate-anchored cyclic RGD peptides. Chembiochem (2005) 0.94

Urokinase-type plasminogen activator (uPA) and its receptor (uPAR): development of antagonists of uPA/uPAR interaction and their effects in vitro and in vivo. Curr Pharm Des (2003) 0.93

RGD-peptides for tissue engineering of articular cartilage. Biomaterials (2002) 0.93

Influence of the internal disulfide bridge on the folding pathway of the CL antibody domain. J Mol Biol (2006) 0.92

High-affinity urokinase-derived cyclic peptides inhibiting urokinase/urokinase receptor-interaction: effects on tumor growth and spread. FEBS Lett (2002) 0.92

Cell adhesion and proliferation on RGD-modified recombinant spider silk proteins. Biomaterials (2012) 0.92

The conformation of cyclo(-D-Pro-Ala4-) as a model for cyclic pentapeptides of the DL4 type. J Am Chem Soc (2006) 0.92

Probing integrin selectivity: rational design of highly active and selective ligands for the alpha5beta1 and alphavbeta3 integrin receptor. Angew Chem Int Ed Engl (2007) 0.92

ADAM15 decreases integrin alphavbeta3/vitronectin-mediated ovarian cancer cell adhesion and motility in an RGD-dependent fashion. Int J Biochem Cell Biol (2005) 0.92

Cell adhesion and polarisation on molecularly defined spacing gradient surfaces of cyclic RGDfK peptide patches. Eur J Cell Biol (2008) 0.91

pH-dependent dimerization and salt-dependent stabilization of the N-terminal domain of spider dragline silk--implications for fiber formation. Angew Chem Int Ed Engl (2011) 0.91

Docking studies on alphavbeta3 integrin ligands: pharmacophore refinement and implications for drug design. J Med Chem (2003) 0.90

The solution structure of BMPR-IA reveals a local disorder-to-order transition upon BMP-2 binding. Biochemistry (2008) 0.90

Synthesis of N-methylated cyclic peptides. Nat Protoc (2012) 0.90