Peptide and Peptide Mimicking Tools: Methods, Synthesis, Design & Applications

1st Edition, Volume 698 - June 18, 2024
Editor: David M. Chenoweth
Language: English
Hardback ISBN:
9 7 8 - 0 - 4 4 3 - 2 1 8 1 4 - 9
eBook ISBN:
9 7 8 - 0 - 4 4 3 - 2 1 8 1 5 - 6

Peptide Chemical Tools for Modulating Biology, Volume 698 in the esteemed Methods in Enzymology series, highlights new advances in the field, with this new volume presenting in… Read more

Peptide and Peptide Mimicking Tools: Methods, Synthesis, Design & Applications

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Peptide Chemical Tools for Modulating Biology, Volume 698 in the esteemed Methods in Enzymology series, highlights new advances in the field, with this new volume presenting interesting topics on Peptide tools that target telomere maintenance, Molecular Design of Peptide Therapeutics, Sulfonyl peptide tools for modulating biology, Peptide tools for targeting the Crk/CrkL-p130Cas axis, Quorum sensing peptide tools, In vivo stability and BBB penetration of peptide tools, and Oligo-benzamide-based peptide mimicking tools for modulating biology.

Cover image
Title page
Table of Contents
Series Page
Copyright
Contributors
Chapter One: Synthesis, derivatization, and conformational scanning of peptides containing N-Aminoglycine
Abstract
1 Introduction
2 Protocols for the synthesis of aGly-containing peptides
3 Tips and troubleshooting
4 Applications to conformational scanning
5 Summary
Acknowledgements
References
Chapter Two: Thioimidates provide general access to thioamide, amidine, and imidazolone peptide-bond isosteres
Abstract
1 Introduction
2 Thioamide peptide-bond isosteres
3 Amidine peptide-bond isosteres
4 (4H)-Imidazolone peptide-bond isosteres
5 Materials
6 Protocol for synthesis of protected thionopeptides
7 Protocol for cleavage & deprotection of protected thionopeptides
8 Protocol for amidinopeptide synthesis via thioimidates
9 Protocol for backbone imidazolone peptide synthesis via thioimidates
10 Summary and conclusions
Acknowledgements
References
Chapter Three: A single backbone amide modification method to achieve single site-specific chemical protein conjugation
Abstract
1 Introduction
2 Developing CAST for a single peptide backbone amide modification
3 Protein labeling using CAST
4 Antibody modification using CAST
5 Developing plasma-stable CASTi
6 Tra-CASTi-MMAE preparation
7 Antitumor activity evaluation of Tra-CASTi-MMAE in vitro and in vivo
8 Summary and conclusions
Acknowledgments
References
Chapter Four: Chemical cyclization of tyrosine-containing peptides via in situ generated triazolinedione peptides
Abstract
1 Introduction
2 Chemoselective cyclization of tyrosine-containing peptides
3 Protocol
4 Summary and conclusions
Acknowledgements
References
Chapter Five: Highly selective chemical modification of poly-His tagged peptides and proteins
Abstract
Abbreviations
1 Introduction
2 Safety considerations
3 Gram scale synthesis of the azidoacetate ester
4 Synthesis of the biotin functionalized ester
5 Recombinant protein expression
6 Preparation of stock solutions
7 Peptide and protein modifications
8 Summary
Acknowledgments
References
Chapter Six: Tetrazine cyclized peptides for one-bead-one-compound library: Synthesis and sequencing
Abstract
1 Introduction
2 Protocols
3 Optimization and troubleshooting
4 Future directions
Acknowledgements
References
Chapter Seven: One-pot ligation of multiple peptide segments via N-terminal thiazolidine deprotection chemistry
Abstract
1 Introduction
2 C-to-N one-pot ligation of multiple peptide segments
3 General protocol for peptide segment synthesis
4 General protocol for one-pot peptide ligation with repetitive Thz deprotection by 2-aminobenzamide type aldehyde scavenger
5 Summary
Acknowledgement
References
Chapter Eight: Molecular design of peptide therapeutics via N-terminal modification
Abstract
1 Introduction
2 N-terminal alkylation using trifluoroethyl iodonium salts
3 N-terminal alkylation by reductive amination
4 Luciferase based cell assay
5 Summary
References
Chapter Nine: Oligo-benzamide-based peptide mimicking tools for modulating biology
Abstract
1 Introduction
2 Design and application of oligo-benzamides as α-helix mimetics
3 Synthetic strategies for producing oligo-benzamides
4 Materials
5 Reagents
6 Synthetic procedural details
7 Summary
Acknowledgements
References
Chapter Ten: Sulfonyl γ-AApeptide tools for modulating biology
Abstract
1 Introduction
2 Crystal structures and rational design
3 Synthesis of sulfonyl-γ-AApeptides
4 Biomedical applications
5 Summary and future directions
Acknowledgements
References
Chapter Eleven: Designing and synthesizing peptide-based quorum sensing modulators
Abstract
Abbreviations
1 Introduction
2 General methodology and design strategy
3 Synthesis of linear quorum sensing peptides
4 Purification & analysis of linear quorum sensing peptides
5 Synthesis of cyclic quorum sensing peptides
6 Conclusion
Acknowledgement
References
Chapter Twelve: Use of phosphotyrosine-containing peptides to target SH2 domains: Antagonist peptides of the Crk/CrkL-p130Cas axis
Abstract
1 Introduction
2 Peptide design and synthesis
3 Protein expression and purification
4 Modeling of peptide–protein complexes
5 Characterization of peptide-protein interaction
6 Modulation of protein-protein interactions by peptides (GST pulldown)
7 Outlook
Acknowledgments
References
Chapter Thirteen: Design and synthesis of oxytocin glycosides for the treatment of pain and substance use disorder
Abstract
1 Introduction
2 Materials
3 Equipment
4 Synthesis of serine lactoside (SerLact)
5 Synthesis of the oxytocin lactoside analogue
6 Discussion
7 Conclusion
References
Chapter Fourteen: Fluorescence polarization assay for screening FANCM-RMI inhibitors to target the alternative lengthening of telomeres
Abstract
1 Introduction
2 Expression and purification of RMI1-RMI2 heterodimer
3 TAMRA fluorescent tracer
4 RMI1-RMI2 fluorescence polarization assay
5 Conclusions
Acknowledgments
References

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David M. Chenoweth