Peptide Macrocycles: Methods and Protocols

Preface...
Table of Contents...
Contributing Authors...

Part I Peptide Macrocycle Synthesis

1. Three Methods for Peptide Cyclization via Lactamization
Laura Posada and Gloria Serra

2.Solid-Phase Peptide Cyclization with Two Disulfide Bridges
Da'san M. M. Jaradat

3.Peptide Macrocyclization through Palladium-Catalyzed Late-Stage C-H Activation
Chuangxu Cai, Shu Liu, and Huan Wang

4.Three Methods for the Solution Phase Synthesis of Cyclic Peptides
Angelika Ullrich, Lukas Junk, and Uli Kazmaier

5.Computational Design of Structured and Functional Peptide Macrocycles
Stephanie Berger and Parisa Hosseinzadeh

6.On-Resin Peptide Cyclization Using the 3-4-Amino-(Methylamino)Benzoic Acid (MeDbz) Linker
Bengt H. Gless and Christian A. Olsen

7.Scalable and Efficient in planta Biosynthesis of Sunflower Trypsin Inhibitor-1 (SFTI) Peptide Therapeutics
Thomas N. G. Handley, Mark A. Jackson, and David J. Craik

8.Ligation, Macrocyclization, and Simultaneous Functionalization of Peptides by Multicomponent Reactions (MCR)
Aldrin V. Vasco, Manuel G. Ricardo, Daniel G. Rivera, and Ludger A. Wessjohann

9.Diels-Alder Cycloadditions for Peptide Macrocycle Formation
Jeffrey E. Montgomery and Raymond E. Moellering

Part II Peptide Macrocycle Combinatorial Library Synthesis and Screening

10.Protein Catalyzed Capture (PCC) Agents for Antigen Targeting
Matthew N. Idso, Bert T. Lai, Heather D. Agnew, and James R. Heath

11.Preparation of Bacterial Cell-Surface Displayed Semisynthetic Cyclic Peptides
Shubhendu Palei, Joachim Jose, and Henning D. Mootz

12.The Discovery of Peptide Macrocycle Rescuers of Pathogenic Protein Misfolding and Aggregation by Integrating SICLOPPS Technology and Ultra-Throughput Screening in Bacteria
Dafni C. Delivoria and Georgios Skretas

13.In Vitro Selection of Thioether-Closed Macrocycle Peptide Ligands by Means of the RaPID System
Takayuki Katoh, Yuki Goto, and Hiroaki Suga

14.MOrPH-PhD: A Phage Display System for the Functional Selection of Genetically Encoded Macrocyclic Peptides
Yu Gu, Jacob A. Iannuzzelli, and Rudi Fasan

15.Discovery of Antimicrobial Peptide Macrocycles Through Bacterial Display
Justin R. Randall, Cory D. DuPai, and Bryan W. Davies

Part III Peptide Macrocycle Characterization

16.Assessing the Cellular Uptake, Endosomal Escape, and Cytosolic Entry Efficiencies of Cyclic Peptides
Heba Salim and Dehua Pei

17.In silico Analysis of Peptide Macrocycle-Protein Interactions
Margaret M. Hurley and Meagan C. Small

18.Binding Characterization of Cyclic Peptide Ligands to Target Proteins and Chemical Epitopes using ELISA and Fluorescence Polarization Assays
Ariane Borges, Iryna Onasenko, and Arundhati Nag

19.Determining the Binding Kinetics of Peptide Macrocycles using Bio-Layer Interferometry (BLI)
Katherine Rhea

Part IV Unique Applications of Peptide Macrocycles

20.Different Approaches to Cyclize a Cell-Penetrating Peptide and to Tether Bioactive Payloads
Lucia Feni and Innes Neundorf

21.Helical Stabilization of Peptide Macrocycles by Stapled Architectures
Fenfang Yang, Feng Yin, and Zigang Li

22.Development and Characterization of Light Responsive Peptide Macrocycles
Lena Sobze and Ratmir Derda

23.Hydrogel Formation with Enzyme-Responsive Cyclic Peptides
Andrea S. Carlini, Mary F. Cassidy, and Nathan C. Gianneschi

24.Cyclization and Self-Assembly of Cyclic Peptides
Alejandro Méndez-Ardoy, Ignacio Insua, Juan R. Granja, and Javier Montenegro

Subject Index List...