Direct access to side chain N,N′-diaminoalkylated derivatives of basic amino acids suitable for solid-phase peptide synthesis

[1]  R. Liskamp,et al.  Peptides and Proteins as a Continuing Exciting Source of Inspiration for Peptidomimetics , 2011, Chembiochem : a European journal of chemical biology.

[2]  Christopher J. White,et al.  Contemporary strategies for peptide macrocyclization. , 2011, Nature chemistry.

[3]  Jan Jezek,et al.  Peptide and glycopeptide dendrimers and analogous dendrimeric structures and their biomedical applications , 2011, Amino Acids.

[4]  L. Gentilucci,et al.  Chemical modifications designed to improve peptide stability: incorporation of non-natural amino acids, pseudo-peptide bonds, and cyclization. , 2010, Current pharmaceutical design.

[5]  G. Zhanel,et al.  Cationic Amphiphiles, a New Generation of Antimicrobials Inspired by the Natural Antimicrobial Peptide Scaffold , 2010, Antimicrobial Agents and Chemotherapy.

[6]  Kent Kirshenbaum,et al.  Peptoid macrocycles: making the rounds with peptidomimetic oligomers. , 2010, Chemistry.

[7]  H. Aoyagi,et al.  Structure‐activity relationship of indolicidin, a Trp‐rich antibacterial peptide , 2010, Journal of peptide science : an official publication of the European Peptide Society.

[8]  Jennifer A. Prescher,et al.  Copper-free click chemistry in living animals , 2010, Proceedings of the National Academy of Sciences.

[9]  J. Zubieta,et al.  Single Amino Acid Chelates (SAAC): A Strategy for the Design of Technetium and Rhenium Radiopharmaceuticals , 2009 .

[10]  J. Bang,et al.  Design of novel indolicidin-derived antimicrobial peptides with enhanced cell specificity and potent anti-inflammatory activity , 2009, Peptides.

[11]  Helen E Blackwell,et al.  Structure-function relationships in peptoids: recent advances toward deciphering the structural requirements for biological function. , 2009, Organic & biomolecular chemistry.

[12]  K. Hahm,et al.  Investigating the effects of positive charge and hydrophobicity on the cell selectivity, mechanism of action and anti-inflammatory activity of a Trp-rich antimicrobial peptide indolicidin. , 2009, FEMS microbiology letters.

[13]  M. Wolfert,et al.  Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions. , 2008, Angewandte Chemie.

[14]  J. Lutz,et al.  Copper-free azide-alkyne cycloadditions: new insights and perspectives. , 2008, Angewandte Chemie.

[15]  P. Cudic,et al.  Pseudopeptide Synthesis via Fmoc Solid-Phase Synthetic Methodology , 2007 .

[16]  Wei-Chiang Shen,et al.  Cell Penetrating Peptides: Intracellular Pathways and Pharmaceutical Perspectives , 2007, Pharmaceutical Research.

[17]  C. Mant,et al.  Role of Peptide Hydrophobicity in the Mechanism of Action of α-Helical Antimicrobial Peptides , 2006, Antimicrobial Agents and Chemotherapy.

[18]  H. Vogel,et al.  Solvent-dependent structure of two tryptophan-rich antimicrobial peptides and their analogs studied by FTIR and CD spectroscopy. , 2006, Biochimica et biophysica acta.

[19]  Vasso Apostolopoulos,et al.  Round and round we go: cyclic peptides in disease. , 2006, Current medicinal chemistry.

[20]  P. Virta,et al.  Synthesis of Bicyclic Peptides , 2006 .

[21]  R. Hancock,et al.  Peptide Antimicrobial Agents , 2006, Clinical Microbiology Reviews.

[22]  T. Heinrich,et al.  Asymmetric synthesis of highly substituted azapolycyclic compounds via 2-alkenyl sulfoximines: potential scaffolds for peptide mimetics. , 2006, Journal of the American Chemical Society.

[23]  Stefan Bräse,et al.  Organic azides: an exploding diversity of a unique class of compounds. , 2005, Angewandte Chemie.

[24]  Wei-Ting Huang,et al.  Structural and DNA-binding studies on the bovine antimicrobial peptide, indolicidin: evidence for multiple conformations involved in binding to membranes and DNA , 2005, Nucleic acids research.

[25]  A. Zega.  Azapeptides as pharmacological agents. , 2005, Current medicinal chemistry.

[26]  H. Brückner,et al.  Marfey’s reagent for chiral amino acid analysis: A review , 2004, Amino Acids.

[27]  J. Zubieta,et al.  Direct reductive alkylation of amino acids: Synthesis of bifunctional chelates for nuclear imaging , 2004 .

[28]  M. Meldal,et al.  Synthesis of 3‐Boc‐(1,3)‐oxazinane‐Protected Amino Aldehydes from Amino Acids and Their Conversion into Urea Precursors. Novel Building Blocks for Combinatorial Synthesis , 2004 .

[29]  J. Mascareñas,et al.  A New [5+2] Annulation Method for the Synthesis of 8-Oxabicyclo[3.2.1]octanes from Pyrones , 2004 .

[30]  R. Hodges,et al.  Effects of single D-amino acid substitutions on disruption of beta-sheet structure and hydrophobicity in cyclic 14-residue antimicrobial peptide analogs related to gramicidin S. , 2004, The journal of peptide research : official journal of the American Peptide Society.

[31]  R. Liskamp,et al.  Automated solid-phase synthesis and structural investigation of β-peptidosulfonamides and β-peptidosulfonamide/β-peptide hybrids: β-peptidosulfonamide and β-peptide foldamers are two of a different kind , 2002 .

[32]  A. Mark,et al.  Mechanism by which 2,2,2-trifluoroethanol/water mixtures stabilize secondary-structure formation in peptides: A molecular dynamics study , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[33]  Lu Th,et al.  A New Tri-Orthogonal Strategy for Peptide Cyclization , 2002 .

[34]  Luke G Green,et al.  A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. , 2002, Angewandte Chemie.

[35]  J. Tam,et al.  Peptide dendrimers: applications and synthesis. , 2002, Journal of biotechnology.

[36]  Morten Meldal,et al.  Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. , 2002, The Journal of organic chemistry.

[37]  S. David.  Towards a rational development of anti‐endotoxin agents: novel approaches to sequestration of bacterial endotoxins with small molecules , 2001, Journal of molecular recognition : JMR.

[38]  M. G. Finn,et al.  Click Chemistry: Diverse Chemical Function from a Few Good Reactions. , 2001, Angewandte Chemie.

[39]  S. Futaki,et al.  Arginine-rich Peptides , 2001, The Journal of Biological Chemistry.

[40]  J. Pelletier,et al.  Improved Solid-Phase Peptide Synthesis Method Utilizing α-Azide-Protected Amino Acids , 2001 .

[41]  K. Pattabiraman,et al.  The design, synthesis, and evaluation of molecules that enable or enhance cellular uptake: peptoid molecular transporters. , 2000, Proceedings of the National Academy of Sciences of the United States of America.

[42]  M. Fridkin,et al.  Structure-function studies of polymyxin B nonapeptide: implications to sensitization of gram-negative bacteria. , 2000, Journal of medicinal chemistry.

[43]  Ü. Langel,et al.  Cell-Penetrating Peptides , 2000, Methods in Molecular Biology.

[44]  J. Vilarrasa,et al.  A practical procedure for the preparation of carbamates from azides , 1999 .

[45]  R. Liskamp,et al.  Solid‐Phase Synthesis of Oligourea Peptidomimetics , 1999 .

[46]  S H White,et al.  CD spectra of indolicidin antimicrobial peptides suggest turns, not polyproline helix. , 1999, Biochemistry.

[47]  B. Wiesner,et al.  Cellular uptake of an alpha-helical amphipathic model peptide with the potential to deliver polar compounds into the cell interior non-endocytically. , 1998, Biochimica et biophysica acta.

[48]  R. Hancock,et al.  Mode of Action of the Antimicrobial Peptide Indolicidin* , 1996, The Journal of Biological Chemistry.

[49]  G. Fields,et al.  Promotion of Fibroblast Adhesion by Triple-helical Peptide Models of Type I Collagen-derived Sequences (*) , 1996, The Journal of Biological Chemistry.

[50]  Wentao Zhang,et al.  Efficient solid-phase synthesis of peptides with tripodal side-chain bridges and optimization of the solvent conditions for solid-phase cyclizations , 1996 .

[51]  John W. Taylor,et al.  A new strategy applied to the synthesis of an α-helical bicyclic peptide constrained by two overlapping i, i+7 side-chain bridges of novel design , 1996 .

[52]  M. Krug,et al.  Synthesis and properties of the first all‐aza analogue of a biologically active peptide , 1995, Journal of peptide science : an official publication of the European Peptide Society.

[53]  B. D. Harris,et al.  A Reductive Amination/Lactamization Procedure Using Borohydride Reagents. , 1994 .

[54]  A. Prochiantz,et al.  The third helix of the Antennapedia homeodomain translocates through biological membranes. , 1994, The Journal of biological chemistry.

[55]  G. Fields,et al.  Melanoma cell adhesion and spreading activities of a synthetic 124-residue triple-helical "mini-collagen". , 1993, The Journal of biological chemistry.

[56]  Stephen B. H. Kent,et al.  Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis , 1992 .

[57]  R. Hodges,et al.  Effect of trifluoroethanol on protein secondary structure: an NMR and CD study using a synthetic actin peptide. , 1992, Biochemistry.

[58]  Wayne L. Smith,et al.  Indolicidin, a novel bactericidal tridecapeptide amide from neutrophils. , 1992, The Journal of biological chemistry.

[59]  D. Wyss,et al.  Template-Assembled Synthetic Proteins with 4-Helix-Bundle Topology - Total Chemical Synthesis and Conformational Studies , 1992 .

[60]  J. Stewart,et al.  Design and synthesis of a peptide having chymotrypsin-like esterase activity. , 1990, Science.

[61]  Maurice Green,et al.  Autonomous functional domains of chemically synthesized human immunodeficiency virus tat trans-activator protein , 1988, Cell.

[62]  E. Blout,et al.  Synthesis of a new type of cyclic peptide: a bicyclic nonapeptide , 1982 .

[63]  R. Lee,et al.  Preparation and some biochemical properties of neoglycoproteins produced by reductive amination of thioglycosides containing an omega-aldehydoaglycon. , 1980, Biochemistry.

[64]  B. Ganem,et al.  A new synthesis of amides and macrocyclic lactams , 1978 .

[65]  R. Borch,et al.  Cyanohydridoborate anion as a selective reducing agent , 1971 .

[66]  J. H. Boyer.  Addition of Hydrazoic Acid to Conjugated Systems1 , 1951 .

[67]  C. Stevenson.  Advances in peptide pharmaceuticals. , 2009, Current pharmaceutical biotechnology.

[68]  Giles R. Scuderi,et al.  The Basic Principles , 2006 .

[69]  Clinical,et al.  Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically : Approved standard , 2006 .

[70]  C. Toniolo,et al.  Synthesis of Peptides and Peptidomimetics , 2003 .

[71]  J. Pelletier,et al.  A new tri-orthogonal strategy for peptide cyclization. , 2002, Organic letters.

[72]  L. Otvos.  Use of Circular Dichroism to Determine Secondary Structure of Neuropeptides , 1997 .

[73]  D. Prockop,et al.  Perspectives on the synthesis and application of triple-helical, collagen-model peptides. , 1996, Biopolymers.

[74]  R. Marks,et al.  The acid-catalysed decomposition of some β-azido-carbonyl compounds , 1967 .