Understanding Biology Using Peptides (eBook)

Dr. Sylvie Blondelle is an Associate Member in Microbiology/Biochemistry at Mixture Science, Inc., San Diego, CA and Head of the Biosafety Department at the Burnham Institute for Medical Research. Her research focuses on strategies toward the development an HIV vaccine through optimization of peptide immunogens. Dr. Blondelle received her Ph.D. in organic chemistry from the University of Montpellier, France, in 1988.

Preface 2
Message from the President of the American Peptide Society 3
19th American Peptide Symposium 5
List of the 19th American Peptide Symposium Sponsors 7
List of the 19th American Peptide Symposium Exhibitors 8
The American Peptide Society 9
American Peptide Symposia 10
The Merrifield Award 12
The Makineni Lecture Award 14
Achievement Award for Scientific and Administrative Excellence 15
Peptide Society Travel Grants 16
Bert Schram Young Investigators’ Mini-Symposium 18
Young Investigators’ Poster Competition 19
Abbreviations 21
Contents 31
Merrifield Award Lecture Dr. Richard A. Houghten 55
From Tens to Trillions - Advances in Synthetic Combinatorial Chemistry of Peptides, Peptidomimetics and Heterocyclic Compounds Derived from Peptides 56
Goodman Memorial 67
Peptides in the Days of Photonics 68
It All Started in Brooklyn, NY, Forty-five Years Ago! 73
Short Transmembrane Peptide Sequences as Nucleation Sites for Globular Protein Folding 77
Synthesis and In Vitro Opioid Activity Profiles of Novel Cyclic Enkephalin Analogs 82
A Photo-Controlled ß Hairpin 87
Structure-Function Relationship Studies of Analogs of PTH( 1- 11) Fragment Containing Combinations of Aib and ( aMe) Nle 89
Membrane Associated Structure of a Ghrelin Agonist as Determined by NMR 91
Scaffold, Dendritic and Metal-Assisted Assembly of Collagen-Like Biomaterials 93
Peptide and Protein Synthesis Strategies 95
Positional Scanning for Peptide Secondary Structure by Solid Phase Synthesis with Aza- Amino Acids and Freidinger Lactams 96
Synthesis of Cyclic Peptides via Transition Metal Catalyzed C-C Bond Formation 99
Solid Phase Synthesis of Phosphorylated Cis and Trans 3- Peptidyl- 4-( 4'- hydroxyphenyl)- ß Lactams 102
Switch on Amyloid ß Peptide Self- Assembly by Enzyme- Triggered Acyl Migration 105
ROMP of Norbornyl Oligopeptides: A Versatile Synthetic Method for Exploring Receptor Topology 108
Native Chemical Ligation at Aromatic Residues 110
Robotic Synthesis of Soluble Peptide Arrays 113
Covalent Capture: Application to Peptides Possessing Auxiliary Groups for Extended Chemical Ligation 115
Asymmetric Induction on a Racemic Amine by Chiral Dipeptide 5( 4H)- Oxazolones from Ca- Methyl Phenylglycine 117
Poly(ethylene glycol) (PEG) Modifications and Conformational Analysis of Thymosin a 1 119
Suppression of Side Reactions Associated with Use of the Benzyloxymethyl Group on Histidine 121
Peptide Synthesis in Water: 2-(4-Sulfophenyl-sulfonyl) ethoxycarbonyl Group and Coupling Reagents 123
Efficient Synthesis in Solid-Phase of Freidinger-like Lactams by Microwave Irradiation 125
Synthesis of Monocyte Chemoattractant Protein 1 (MCP-1) Analogs via Native Chemical Ligation 127
NMR Analysis of a Multi-domain Peptide of the Saccharomyces cerevisiae Alpha Factor Receptor 129
Further Studies on an Alternative Approach to Prepare Esterified Protected Peptides under Mild Conditions 131
A Long Range S,N-Acyl Migration by Silver Ion Assistance in Thioester Ligation 133
The C-Terminal Fragment of Acanthoscurrin is a Difficult Sequence 135
A Novel Approach to Resin-based Cysteine Alkylation 137
Deprotection of the p- Methoxybenzyl Group of Selenocysteine by Neighboring Group Participation 139
Overcoming Challenges in Automated Long Peptide Synthesis – A Multi- pronged Approach 141
Synthesis and Biological Evaluation of Antagonist Analogs of the Peptide Hormone Oxytocin 143
Development of Wang Resin Supported Evans-type Oxazolidinone for Asymmetric Reaction 145
A Convenient Synthetic Method for Monodehydro-2,5- diketopiperazines 147
Solid-Phase Synthesis of Azole-Based Peptides and Peptidomimetics 149
Efficient Synthesis of N- Methylamino Acids Compatible with Fmoc Solid- Phase Peptide Synthesis 151
The “ O- Acyl Isopeptide Method” for the Synthesis of Alzheimer’s Disease- Related Amyloid ß Peptide ( Aß) 1– 42 153
The “ O- Acyl Isopeptide Method” for the Synthesis of Difficult Sequence- Containing Peptides: Application to the Synthesis of Alzheimer’s Disease- Related Amyloid ß Peptide ( Aß) 1– 42 Mutants 155
Enhancing Atom Economy of SPS: Recoverable and Reusable Building Blocks for Depsipeptide Synthesis 157
1-N-Methyl-Histidine as a Side-Product in Backbone N- Methylated PTH Analogs 159
Combinatorial Approach in the Synthesis of a Small Library of ß Turn Structures Based on Thiazolidine Moiety 161
Solid-Phase Peptide Synthesis Using ChemMatrix®, a Polyethylenglycol (PEG)-based Solid 163
p- Nitrobenzyloxycarbonyl (pNZ) as an Alternative to Fmoc for the Protection of Amines in Solid- Phase Peptide Synthesis 165
Synthesis and NMR Analysis of CCR5 and CXCR4 Peptides Containing Tyrosine Sulfate 167
Steroid-Peptide Conjugates 169
Influence of Natural Loop Residues or Oligolysines on the Biophysical Properties of Transmembrane Domains of a G Protein- Coupled Receptor 171
Design, Synthesis and Analysis of Constrained B-Cell Epitope from HER- 2 Protein 173
Synthesis of the Four Stereoisomers of N-Fmoc-O-t-Bu-4,4,4- trifluorothreonine 175
Synthesis of Na- Fmoc-Ne-[( 2- nitrophenyl) acetyl]- lysine ( Fmoc- Lys( Npa)- OH) and its Applications in Solid- Phase Peptide Synthesis 177
A MS-based Encoding Method for OBOC Combinatorial Branched Peptide Libraries 179
Sequential Chemical Ligation for Polypeptide Synthesis by the Combination of the Thioester Method and the Extended Chemical Ligation Using a Photoremovable Auxiliary 181
Solid-Phase Synthesis of a Mucin Glycopeptide Segment from CD43 for NMR and Crystallization Studies 183
SPPS of Bacterial Addressed Peptides and PNAs Overcoming the Resistance against Antibiotics 185
Convergent Synthesis of the Cysteine-rich Mdm2 RING Finger Domain 187
Evaluation of Polyamide-Polystyrene Block Polymers in Peptide Synthesis and Biochemistry 189
New Nomenclature for Complex Cyclopeptides 191
New Approaches for Native Chemical Ligation 193
Microwave-Assisted Solid-Phase Peptide Synthesis (MW-SPPS) on CLEAR Supports 195
Microwave Assisted Peptide Synthesis – A Tool to Replace Classical SPPS? 197
Fast and Versatile Peptide Backbone Modifications Using Microwave Energy 199
Microwave-Assisted Synthesis of Multivalent Dendrimeric Peptides using Cycloaddition Reaction (‘ Click’) Chemistry 201
Efficient Synthesis of Disulfide Bridge Containing Peptides: Melanin Concentrating Hormone ( MCH) and Brain Natriuretic Peptide ( BNP) 203
Rapid Solution-phase Synthesis of a 20-mer Peptide According to the DioRaSSP® Method 205
A New Efficient Post-Assembly Strategy for the Synthesis of Sulfated Peptides 207
Auxiliary Group-Assisted Peptide Thioester Preparation Based on On- resin N- S Acyl Shift Triggered by TFA Treatment 209
Determination of an Optimal Solid Support for Use with Microwave- Assisted Solid- Phase Peptide Synthesis 211
Efficient Recombinant Production of the 16 Amino Acid Peptide AOD9604 213
Chemical Synthesis of the Gsti Protein by a NCL Method on a X-Met Site 215
N,O-Acyl Shifts: Unexpected Side-Reaction and Beneficial Tool in Fmoc- Chemistry 217
Magnetic CLEAR Beads for Solid-Phase Synthesis of Peptides and Affinity Ligands 219
An Efficient and Facile Synthesis of Tyrosine-Sulfate-Containing Peptides: Synthesis of the N- Terminal Peptide of CCR5 and Its Analog 221
Interaction of DPH with the Local Anesthetic Receptor Site in D1- S6 of the Na+ Channel by NMR and Molecular Modeling 223
The Structural Determinants of GPCR Binding and Activation: Insights from Mutagenesis and Molecular Modeling Studies of the Human Angiotensin II Type 1 ( hAT1) Receptor 225
Protein Epitope Mimetics A New Approach to Target Protein- Protein Interactions 227
Application of Phenylphosphate Mimetics to the Design and Synthesis of Olefin Metathesis- Derived Grb2 SH2 Domain- Binding Macrocycles 229
Radiolabeled Peptides as CXCR4 Ligands 231
Aza-peptides with Multiple Aza-amino Acids, Synthesis and Preliminary Conformational Analysis of Glu- azaAla- Ala- azaAla- Leu- azaAla- Lys- azaAla- NH2 233
Design and Synthesis of Bicyclic Internal Internal -Turn Mimetics and their Applications toward Biologically Interesting Ligands 235
Synthesis and Incorporation of Freidinger Lactam Analogs in GHRP- 6 237
Microwave-assisted Synthesis of N- glycosylated Building Blocks 239
Parallel Solid-Phase Synthesis of Mucin-Like Glycopeptides from an an - GalN3 O- Linked Threonine Building Block 241
Synthesis of Silyl Ether Linkers for Solid-Phase Peptide Synthesis 243
Synthetic Routes to, and Mechanistic Understanding of, Dithiasuccinoyl ( Dts)- Amines and Chlorocarbonyl Carbamoyl Disulfanes 245
Peptide-Derived (Sulfonyl)Azides as Versatile Synthons in Chemoselective Bioconjugations 247
Chemically Synthesized Annexin-A5-Based Probes for Molecular Imaging 249
Unequivocal Synthesis of ( Z)- Alkene or (E)- Fluoroalkene Dipeptide Isosteres via DKP Mimetics to Probe Structural Requirements of Peptide Transporter 251
Development of New Photoremovable Amino Protecting Group and its Application toward Chemical Synthesis of 7TM- GPCR 253
Multivalent Peptide Dendrimers: Native Chemical Ligation as a Synthetic Tool 255
Synthesis and Use of C-terminally Biotinylated Peptidomimetics with High Grb2 SH2 Domain- binding Affinity 257
Total Solid Phase Synthesis of a Marine Cyclodepsipeptide IB- 01212 259
Interference with Protein-Protein Interactions Involved in Protease Inhibitor Complex Formation 261
Sequence-Enabled Reassembly (SEER) Peptides for the Detection of DNA Sequences 263
A Mild Acidic Method for the Selective Deprotection of N1- trityl- 3a- hydroxypyrrolo[ 2,3- b] indole Derivatives 265
Enantiomerically Pure H-Arg(Z)2-aldehyde Diethylacetal: A Useful Building Block in the Synthesis of Peptide Aldehydes 267
Chlorotrityl Chloride (CTC) Resin as a Convenient Reusable Protecting Group 269
Synthesis and Purification of Multiphosphorylated Peptides 271
Dealing with the Aggregation Problem of Polyglutamine Peptides: Synthesis Strategies 274
Biosynthesis of Bioactive Peptides 276
Synthesis and Biological Assessment of Insulin-Like Analogs with Differential Activity at the Insulin and IGF- 1 Receptors 277
Biosynthesis of the Cyclotide Kalata B1 using Protein Splicing Tools 283
Exploration and Elaboration of Reported Insulin Superagonism through Site- Selective Replacement at TyrB26 285
Synthesis of an RNase B 30-124 Glycoform by Native Chemical Ligation 287
New Themes in Anti-Microbials and Quorum Sensing 289
Threaded Rings and Complex Topologies in Antimicrobial Peptides: Nature’s Engineering Templates 290
A Minimalist Approach to Antimicrobial Proteins with Thionin as a Template 295
Discovering Additional Chemical and Biological Functions for 3- Oxo- N- Acylhomoserine Lactones 299
Comparing Antimicrobial and Membrane Permeabilizing Activity of Peptides Derived from Human Cationic Proteins 302
Preliminary NMR Analysis of ProP440-500 the C-Terminal Cytoplasmic Domain of Bacterial Osmosensory Protein ProP 305
Synthesis and Conformation of Analogs of the Antiviral Peptide Halovir A 308
Total Synthesis in Solution and Preliminary Conformational Analysis of TOAC- Labeled Alamethicin F50/ 5 Analogs 310
A Lipid Monolayer Made Permeable to Tl(I) Ions by the Lipopeptaibol Trichogin GA IV 312
A Universal Influenza B Peptide Vaccine 314
Design, Synthesis and Analysis of a Cysteine-Deleted Analog of the Antimicrobial Peptide Tachyplesin- I 316
Progress toward Total Solid-Phase Synthesis of Cyclic Lipodepsipeptide Antibiotic Fusaricidin A 318
Biological and Structural Characterization of a New Linear Gomesin Analog 320
Monomeric Analogs of Halocidin 322
Fragment of Human Lysozyme Conjugated on the N-terminus and Displaying Antibacterial Properties 324
Synthesis and Raman Spectroscopy Studies of the Antimicrobial Peptide Cecropin B2 326
Alamethicin Interaction with Lipid Membranes: A Spectroscopic Study on Synthetic Analogs 328
Design of Bactericidal Self-Assembling Cyclic D,L-a-Glycopeptides 330
Designer Multifunctional Antimicrobial Peptides Kill Fluoroquinolone- Resistant Clinical Isolates 334
Solution Structures of Stomoxyn and Spinigerin, Two Antimicrobial Peptides from Insects 336
Rational Design of a Helical Antimicrobial Peptides 338
Dimer Formation of Novel Cationic Antimicrobial Peptides in Membrane Environments 340
Post-Translational Modifications of Peptides and Proteins 342
Enzymatic Incorporation of Prenyl Azides into Peptides and Proteins: Tools for Selective Protein Labeling 343
N- Alkylaminooxy Amino Acids as Versatile Derivatives for " Post- Translational" Modifications of Synthetic Peptides 346
Improved Synthesis of 5-hydroxylysine (Hyl) Derivatives 349
Synthesis and Biological Assessment of Sulfonic Acid-Based Glucagon Antagonists 351
Thioester Bond Liability: Study on Natural Influenza and Model Acylpeptides 353
Chemical Synthesis of MUC2 Tandem Repeat Model Carrying Multiple O- GalNAc Moieties 355
Site Specific Introduction of Unnatural Amino Acids at Sites Critical to Insulin Receptor Recognition and Biological Activity 357
Towards Peptides as Potential Therapeutics 359
Target-Based Proteolytic Profiling for Characterizing Cancer Progression 360
From Simple Consensus Peptides to High Affinity Ligands: A Stepwise Diversity Oriented Strategy for the Acquisition of Potent Signaling Inhibitors 365
Cyclic Modular ß Sheets 370
Apolipoprotein A-I Mimetic Peptides 374
Understanding BBB Transport using Glycosylated Enkephalins and Endorphins 377
Design and Study of Novel Peptide Inhibitors against the SARS-Coronavirus Spike Protein 380
Screening Biosynthetic Peptide Libraries for Antimicrobial Activity 383
Cellular Delivery and Design of Proprotein Convertase Inhibitors 386
Mechanism of Interaction between the (17-31) Binding Domain of PTH and the PTH Receptor 389
[3,3]-Sigmatropic Rearrangments, and Chiral Aziridines for the Asymmetric Synthesis of Novel Amino Acids 392
A Library of Cysteine-Biotine Derivatives Useful for Pretargeting Avidin- Biotin Radioimmunoscintigraphy 394
A Methionine Scan of Region [168-176] of the Parathyroid Hormone Receptor 1 – The “ Magnet Effect” 396
A New Approach to the Synthesis of Policyclic Dipeptide Derivatives as Potential Antitumoral Agents 398
A Purification Strategy for Synthetic Peptides that Utilizes pH to Optimize Selectivity 400
Agonist Activation of the Angiotensin II Type 1 Receptor Alters the Spatial Proximity of Transmembrane Domain 7 to the Ligand Binding Pocket 402
An Asymmetric Synthesis of ( R)- and (S)-o- cyano- phenylalanine Leading to Chiral Constrained Phenylalanine Dipeptide Mimetics 404
Analogs of Multifunctional Ligands for Opioid and CCK Receptors 406
Antigen Effects of Peptide Nucleic Acids on HIF-1 1 Expression 408
Novel Glyco-lipid-arsenicals (III) with Anti-proliferative Effects on MCF- 7 Human Breast Cancer Cells 410
Antisense PNA and PNA-peptide Conjugates for the Modulation of ß globin Gene Splicing 412
ß-Amino Acid Analogs of an Insect Neuropeptide 414
Branched Neurotensin for Tumor Targeting 416
CCK/MSH Analogs and Derivatives for Imaging and Incorporation in Multimeric Ligands 418
Cellular Uptake of Pyrrolidine-Based Oxy-Peptide Nucleic Acid 420
Chemical Biology and Biomedical Application of Synthetic Molecules Targeted to Apoptosis Regulated by the Bcl- 2 Family 422
Comparative Immunogenicity of Common and Rare HIV Mutant Peptides 424
Conformational Studies of Agouti-Related Protein (AGRP)- Melanocortin Chimeric Peptides 426
C-Terminal Ether Analogs of NN703 428
Cyclic Statine-based Peptides as Inhibitors of ß Secretase 430
Design and Structure Determination of a Selenium Labeled Antimicrobial Peptide 432
Design and Synthesis of Encoded One-bead One-compound Peptidomimetic Libraries for Identification of a4ß1 Integrin Ligands 434
Design and Synthesis of Histone Deacetylase Inhibitors by Side Chain Modification of 2- Amino-( n- 1)- alkenoic Acids 436
Design of a Library of Histone Deacetylase Inhibitors Based on Chlamydocin 438
Design of an Antibody for Early Detection of Ovarian Cancer 440
Design, Synthesis and Applications of Cell-penetrant Peptides as Signal Transduction Modulators 442
Novel MTII/AGRP Hybrid Analogs that Lead to Selective Ligands for the Human Melanocortin Receptors 444
Design, Synthesis, and Evaluation of Gluten Peptide Analogs as Selective Inhibitors of Human TG2 446
Novel Blue- and Red-Shifted Internally Quenched Fluorogenic Substrates for Continuous Monitoring of SARS- CoV 3CLpro 448
Discovery and Optimization of a TRAIL R2 Agonist for Cancer Therapy 450
Development of Peptide Vaccines against HPV-16 Associated Cervical Cancer and Group A Streptococci 452
Disulfide as a Constraint to Build Super Potent and Selective Melanocortin- 4 Receptor ( MC4R) Agonists 454
Effect of Dimerization and Tetramerization on the Potency of HIV- 1 Integrase Inhibitory Peptides 456
The Effects of Stable Bradykinin Receptor 2 Agonist B9972 on Pulmonary Vasculature in vitro and vivo 458
Etk/Bmx Tyrosine Kinase Peptide Substrates and Inhibitors Derived from the Autophosphorylation Site of the Enzyme 460
Fluorescence Resonance Energy Transfer Substrates for Determining Cathepsin B pH Specificity 462
Ghrelin Attenuates Burn-induced Cachexia 464
High Affinity High Specificity a4ß1 Integrin Targeting Peptidomimetics for Lymphoid Cancers 466
Highly N- Methylated Somatostatin Analogs: Synthesis, Biological Activity and Structure- Activity Relationship Studies 468
Highly Sensitivity FRET Substrate for Assay of HCV Protease 470
Identification and Characterization of Synthetic Peptide Substrates and Small Molecule Inhibitors of Non Receptor Tyrosine Kinase Etk 472
Identification of High Affinity Anti-MCP-1 Antibodies using Synthetic Proteins 474
Mapping Cell Binding using Collagen III “Toolkit” 476
Modeling of a1 Adrenergic Receptors: the Application in the Design of Selective a1B-Adrenergic Antagonists 478
Characterization of the Interaction of HIP Analog Peptide with Heparin 480
New Urotensin-II Analogs Modified at Position 4 482
New Urotensin-II Analogs with a Constrained Trp-7 Side Chain 484
Novel GnRH Antagonists Derived from Degarelix: Exploration of the GnRH Antagonist Pharmacophore 486
Novel Neuroprotective Neurotrophic NAP Analogs Targeting Iron Toxicity and Oxidative Stress in Neurodegenerative Diseases 488
One-bead One-compound: Different Type of Screening Assays for Anti- bacterial Adhesion 490
Peptide - Mediated Delivery of siRNA via Noncovalent Complexes and Covalent Conjugates 492
Peptides Reproducing the ApoA-I 141-164 Region: Studies on Hpt Recognition 494
Peptidomimetic Inhibitors of Platelet Adhesion as Potential Novel Antiplatelet Agents 496
Peptidyl-based Delivery Systems as a Strategy for the Therapeutic Intervention of Human Astrocytoma and Medulloblastoma 498
Photolabeling with N-Terminal Urotensin II Photoprobes Identifies Methionine 288 of Rat Urotensin Receptor as a Contact Point 500
Protein Kinase C Isoform (PKC) Peptide Activator/Inhibitors Exert Cardioprotective Effects in Polymorphonuclear Leukocyte ( PMN)- induced Ischemia/ Reperfusion ( I/ R) Injury 502
Rational Design of Small Molecules for a Novel Class of Anti- Cancer Drugs using a Phenylalanine Library 504
Repair of Photodamaging Effects on Human Melanocytes by 4- Phenylbutryl-His-D-Phe-Arg-Trp-NH2. A Superpotent Analog of a-Melanocortin 506
RGD Peptide-Labeled Quantum Dots for Integrin avß3 Targeting 508
Rigid Cyclic Tetrapeptides as Probes and Mimics of Reverse Turns 510
Solid-Phase Synthesis and Structure Characterization of N’- Biphenyl- N- 2- Ethylbutyl- Demethylvancomycin 512
Stereo-controlled Synthesis of [L-Arg, L/D-3-(2-Naphthyl)alanine]- type (E)-Alkene Dipeptide Isosteres and its Application to the Preparation and Biological Evaluation of Peptidomimetic Analogs of the CXCR4 Antagonist FC131 514
Stochiometric Inhibition of ß-Amyloid Fibrillogenesis using Ca,a-Disubstituted Amino Acid Containing Peptides 516
Structure Determination of the Human Angiotensin II Receptor Type 1 by the Methionine Proximity Assay 518
Structure-Activity Relationship Studies of a Novel CXCR4 Chemokine Antagonist Reveal Unique Activity Profile 520
Studies on a Mutual Prodrug of Sulfamethoxazole and Nalidixic acid 522
Studies on Interaction of CaM with CaM-Binding Peptides M13 and RS20 in the Presence of Al3+ Ions 524
Studies on the Peroxidase Mimetic Peptide 526
Use of Combinatorial Peptide Libraries and LC/MS/MS to Study TPP I Substrate Specificity 528
Sunflower Derived Trypsin Inhibitors as Anti-Metastatics 530
Surface Plasmon Resonance- and Quartz Crystal Microbalance-based Methods for Detecting GRB2 SH2 / Peptide Interaction 532
Synthesis and Biological Activity of Terlipressin and its Putative Metabolites 534
Synthesis and Evaluation of Neuroprotective a,ß-Unsaturated Aldehyde Scavenger Histidyl-containing Analogs of Carnosine 536
Synthesis, Structural Characterization and Reactivity Study of Humanin, an Alzheimer’s Disease Associated Peptide 538
Synthesis of 4-amino-1,2,4,5-tetrahydro-2-benzazepine-3-ones and Study of their ß-turn Inducing Properties 540
Synthesis of a RGD Peptide-PEG Hybrid for Carrying Adenovirus Vector into Cells 542
Synthesis of Cyclic Imino Acids from a Amino-w Bromoalkanoic Acids 544
Synthesis of Quantum Dots Labeled Short Peptides and their Application in Imaging the T Cell Surface Receptors 546
Synthesis of Quantum Dot-Signal Peptides Bioconjugates and Targeting in Living Cells 548
Synthesis of Symmetrical Dimeric Dicarboxylic Acid Linked Peptides on Solid Support 550
Systematic Study on the Structure-Activity Relationship of Pyrazinone Ring- Containing Bioactive Opioid Ligands 552
Tetra and Pentapeptide Derivatives of Hemiasterlin. Synthesis and Activity Studies 554
The Chemo-enzymatic Synthesis of Oligosaccharide-linked Peptides Aimed at Improved Drug Delivery 556
Neokyotorphin as Cell Protein Kinase Affector 558
Towards Inhibition of Amyloid ß protein Oligomerization 560
Use of Betidamino Acids in Drug Design 562
Helical Peptide Analogs of gp41 to Develop an HIV Vaccine 564
Structure-Activity Relationship Studies of a Novel AGRP-Melanocortin Chimeric Template 566
Synthesis and Pharmacological Evaluation of a New Generation of TIPP- Derived Dual- Labeled Ligands for Delta Opioid Receptors 568
Synthesis and Pharmacological Evaluation of Dual Labeled Delta Opioid Receptor Peptides 570
Novel Retro-inverso Envelope Peptide Mimetic Fusion Inhibitors as a Potential Therapy for HTLV- 1 Infected Individuals 572
Heteroclitic Analogs Derived from the HTLV-1 Gag Antigen Increase Cytolytic and IFN- IFN- Responses in HLA- A* 0201 Transgenic Mice 574
Development of a Monoclonal Antibody Therapeutic for the Prevention and Treatment of Pseudomonas aeruginosa Infection 576
An Unexpected Side Reaction Involving the Deletion of an Acetylated N- Methyl- Amino Acid from the N- terminus of Peptides 578
Synthesis and Biological Activities of Chimeric Bioactive Peptides Based on Amino Acids Coupled to 4- Anilino- N- Phenethyl- Piperidine 580
Discovery of Potent mMC1R Agonists with Prolonged Activity at Human Melanocytes 582
Peptide and Protein Design 584
ß Hairpin Minimization and Optimization 585
Analogs of Interleukin 8 Containing non Proteinogenic Segments Show High Biological Activity 588
Optimization of the C-terminal Sequence in Glucagon to Maximize Receptor Affinity 591
Design, Synthesis, and Evaluation of Piperazine-Based Small Molecule Peptide Mimetics Targeting the Melanocortin Receptors 594
Structure-Based Design and Structure-Activity Relationships of D-Phe-Pro-D-Arg-P1'-CONH2 Tetrapeptides Inhibitors of Thrombin 597
A Gibberellin Mimetic Peptide Recognized by an Anti-gibberellin Monoclonal Antibody 599
Synthesis of the Spin-labelled ß Amino Acids cis- and trans- ß TOAC, and a Preliminary Conformational Study of trans- ß TOAC/ trans- ACHC Peptides 601
High Affinity Grb2 SH2 Domain-Binding Macrocycles Derived from Ring- Closing Methathesis of Alkenylglyicne Residues with ß Vinyl Phosphotyrosyl Mimetics 603
Towards Photo-Controlled Collagens 605
Template-Assembled Peptide Models of the N-Peptide Helix Bundle from HIV- 1 gp41 607
Alignment of Three Nitroxide Radicals on the Same Face of a Helical Peptide Scaffold 609
Design, Synthesis, and Preferred Conformation of Peptides Based on a Highly Constrained, ß, ß Diphenyl Substituted Cyclopropane a Amino Acid 611
Identification of a Novel HIV-1 Neutralizing Antibody Using Synthetic Peptides that Mimic a GP41 Fusion Intermediate 613
Covalent Trimeric Coiled Coils of the HIV gp41 HR1 Region are Extremely Potent and Broadly Neutralizing Inhibitors of Viral Infection 615
Selective Agonists for the Human Vasopressin V1b Receptor are Potent Antidiuretic Agonists in the Rat 617
Prion Protein Misfolding: Conformational Stability of the a2 Helix 619
Modeling Flexible Loops in the Dark-Adapted and Activated States of Rhodopsin, a Prototypical G- protein- Coupled Receptor 621
Deducing 3D Models of the Activated States for TM Regions of GPCRs by Modeling Constitutively Active Mutants: The Test Case of Opsin 623
Identification of a Unique Stability Propagation Site that Controls Protein Stability of of - Tropomyosin: a Two- Stranded Stranded - Helical Coiled- coil 625
The Introduction of Uncharged Uncharged -Hydroxymethyl Amino Acid Residues in Substrate Specificity P1 Position of Trypsin Inhibitor SFTI- 1 from Sunflower Seeds Retains its Activity 627
Molecular Simulation of an an a / e-Peptide Dendrimer 629
A GHS-1a Receptor Agonist that is Highly Effective in Stimulating Body Weight Gain 631
A Non-Competitive Peptide Agonist of GHSR1a Receptor Stimulates Growth Hormone Secretion and Food Intake 633
Development of µ Opioid Receptor Selective 4- Anilinidopiperidine Analogs 635
A Whole-Cell Binding Assay for Testing the Targeting Potential of Cyclic Peptide Ligands 637
Synthesis and Evaluation of Chiral and Achiral a,a Disubstituted Amino Acids as ß Sheet Stabilizing Factors 639
Evaluation of Malarial Protease Plasmepsin Inhibitors Containing Hydroxymethylcarbonyl Isostere 641
Design and Synthesis of ß-Secretase Inhibitors: Optimization at the P4 and P1’ Positions 643
Synthesis of Non-linear Potential Vaccines for HSV-1 645
Intramolecular Triplet Quenching by Nitroxide Radicals as a Tool for Determining Peptide Secondary Structure in Solution 647
A Time-Resolved Spectroscopic Study on Peptide Folding 649
Synthesis and Biological Activities of Proline Rich Cyclic Heptapeptide Hymemanide B Analogs 653
Synthesis and Biomaterials Application of Polymers Containing Pentapeptide and/ or Hexapeptide Sequences Derived from Elastin 655
Synthesis and Biological Activities of fMLP Analogs Containing 2,3- Cyclopropane Amino Acid Derivatives 657
pI- shifted Basal Insulin Analogs with High Selectivity for Insulin vs IGF- 1 Receptor 659
N-Backbone Methylations of Parathyroid Hormone (PTH) C-Terminal Region: Bioactivities and Implications for PTH-Receptor Complex 661
N-Backbone Methylations of Parathyroid Hormone (PTH) C-Terminal Region: Effects on Structure 663
C-Terminal Modified Parathyroid Hormone: Effects on Structure and Activity 665
Spectroscopic Characterization of PEG-Amylin Derivatives 667
Conformational Properties and Functional Role of VDAC N-Terminal Peptide 669
Design of Membrane Active Peptides with Regularly Repeating Glycine or D-amino Acid Residues 671
Design and Synthesis of Novel a -MSH Peptide Analogs Highly Selective for the hMC4R 673
Design, Synthesis and Characterization of Conformational Peptides at the Interface of HER- 2 Dimerization and Pertuzumab Binding 675
Synthesis of a Phosphino Triple Helical Collagen Mimic 677
Steric Hindrance of the HER-2/neu Dimerization Loop by Peptide Mimic Antibodies 679
Hydrogen/Deuterium Exchange Studies on Helical Peptides in a DMSO/ MeOD Solvent System 681
Octapeptide Analogs of Somatostatin Containing a,a Dialkylated Amino Acids with Potent Anticancer Activity 683
Backbone Cyclization Improves the Enzymatic Stability of z - Conotoxin, MrIA, whilst Maintaining its Structure and NET-Modulating Activity 685
De novo Design of Peptide Folds of Stereochemically Rationalized Molecular Architecture 687
Restructuring Artificial Peptide Networks by External Triggering 689
Development of a Stilbene-type Photoswitchable ß Hairpin Mimetic 691
The Guanidinium Group: A Key Player in Molecular Recognition 693
Novel and Highly Selective Antagonist Scaffold for Human Melanocortin 3 Receptor: Computer- Aided Design and Biological Evaluation 695
Transmembrane Peptide Segments of the Uncoupling Protein-1: Chemical Synthesis and Biophysical Properties 697
Discovery and Optimization of ß MSH Derived Melanocortin- 4 Selective Agonists 699
Molecular Mechanisms of Constitutive Activity: Mutations at Position 111 of the Angiotensin AT1 Receptor 701
A Surprise End to 20 Year Search for Selective Agonists for Rat Vasopressin V1b Receptor 703
Furanoid Sugar Amino Acids in Design of Analogs of VIP Receptor Binding Inhibitor 705
Two Residues at the Extracellular Face of TM5 and TM6 Interact in the Active State of a G Protein- coupled Receptor 707
Molecular Probes for Visualizing Angiogenesis 709
The Two Cysteine-rich Head Domains of Minicollagen from Hydra Nematocysts Differ in their Cystine Framework and Overall Fold despite an Identical Cysteine Sequence Pattern 711
Polypeptide Ligands Containing Switchable Flexible Linkers as Retractable Inhibitors of Protein- Protein Interactions 713
Helix Formation in a/ß , a/y , and ß/y Hybrid Peptides 715
Nanometer-Scale Amino Acids for Biomolecular Nanotechnology 717
Design and Synthesis of Target-specific Contrast Agents 719
Design and Synthesis of Novel Chromone Based Peptidomimetics 721
Determination of Intrinsic Hydrophilicity/Hydrophobicity Coefficients of Amino Acid Side- Chains using Synthetic Model Peptides 723
Peptide Structures in Material Science and Disease 725
Peptide Reptation as a Mechanism for Rearrangements within a ß-Sheet Aggregate 726
The HIV-1 Fusion Peptide has Amyloid Properties 729
Self-Assembly of Collagen Mimetic Peptides 731
Engineered Synthetic Peptide Epitopes from the Extracellular Domain of HER- 2/ neu are Recognized by Trastuzumab 733
Mapping Protective Epitopes for Anthrax and Plague Vaccine Antigens by LC- MS/ MS 735
Co-assembling Peptide based Biomaterials 737
Three-Dimensional Solution Structure of the PAS1 Domain of Phytochrome A from Rice 739
Membrane Initiated Gelsolin Amyloid Formation 741
Cooperative Formation, Transformation, and Collapse of Hydrogen- Bonds in Polypeptides 743
Reversible Insulin Self-Assembly under Carbohydrate Control 745
Influence of the Nucleophilic and Electrophilic Properties of Solvents for Peptide Solubilization: CD Monitoring and the Special Effect of the Water Molecule 747
VCD Spectroscopic Analysis of the Exendin-4 Truncated Analog TC5b 749
Type II ß-Turn Formation in Tetrapeptides Evidenced by Vibrational Circular Dichroism Spectroscopy 751
The Conformational Preference of Ca-Centered Protein Radicals 753
Impact of a Single a,a Disubstituted Amino Acid on ß Hairpin Folding 755
RGD-Cy7 Conjugates as Near-Infrared Fluorescence Probes to Image a vß3 Integrin Expression in Brain Tumor Xenografts 757
Parameters Influencing Helix Stability of Oligourea Foldamers 759
The Tertiary Structure of Aß1-40 Determined by Scanning Tunnelling Microscopy 761
Validation of Active-Site Mapping of Enzymes 763
Peptide and Protein Arrays 765
Protein Arrays as Tools for Detection of Protein-Protein Interactions by Mass Spectrometry 766
New Tools for the Site-Specific Attachment of Proteins to Surface 769
Designed Peptide Microarrays for Protein Detection and Characterization 772
Luminescent Cd Te Quantum Dots/Albumin Conjugates: Preparation, Fluorescence, Characterization and Labeling of C. Elegans 775
SC2: A Novel Process for Manufacturing of High Density Multi- Purpose Chemical Micro- Arrays 777
High Throughput Preparation of Peptide Arrays Containing Two Fluorescent Dyes Focusing on Practical Protein Detection Systems Systems 779
Identification of Antioxidant Peptides using SPOT Synthesis 781
Water Channel (Aquaporin 3) Gene Activation Correlates with Substance P in ARDS 783
Proteomics and Emerging Technologies 785
RDC as a New NMR-Parameter for Peptides 786
Examination of the Role of Lipid Rafts in GPCR Signal Transduction Using Plasmon Waveguide Resonance ( PWR) Spectroscopy 789
Switchable Inteins: New Tools to Control Protein Function by using Regulated Protein Splicing 793
Pin1: Inhibitors and Mechanism 798
Discovery and Structural Optimization of High Affinity Co- Agonists at the Glucagon and GLP- 1 Receptors 802
Development of a Lanthanide-based Assay for d Opioid Receptor 804
Interaction between a Minimum Hevein Domain and Chitooligosaccharides Studied by NMR and a Novel Surface Plasmon Resonance Method 806
Cross-Reactivity Studies of rMOGED with Synthetic Putative Autoantigens CSF114( Glc) and [ N31( Glc)] hMOG( 30- 50) in Multiple Sclerosis Patients’ Sera 808
Thiohydantoins – A Technique for Labeling Peptides and Proteins 810
Photodimerization in Substituted di- and Oligopeptides by UV- light for Optical Data Storage 812
Does an Aberrant Glucosylation Trigger Autoimmunity in Multiple Sclerosis? 814
Phosphopeptide Proteomics with On-Bead Chemical Synthesis and Display on PEGA Support 816
Optimization of Multiple Sclerosis Antigenic Probes by a Combinatorial Approach 818
Antiproliferative Effect of Lamprey Gonadotropin-releasing Hormone III on Cancer Cells from Non- reproductive Organs 820
New Cyclotide Precursor Sequences 822
Development of an Efficient Multiple Sclerosis Diagnostic Technology Based on an Optical Glycopeptide Immunosensor 824
Author Index /Subject Index 826
Authors 827
Subject 841