Teaching an old scaffold new recognition tricks: oligopyrrolamide antagonists of IAPP aggregation


Sunil Kumar, Maria C. Vogel and Andrew D. Hamilton
Org. Biomol. Chem., 2018,16, 733-741
From themed collection: Chemical biology in OBC

Abstract

An oligopyrrolamide was identified as a potent antagonist of the aggregation of IAPP, a process associated with type 2 diabetes.


Synthesis and characterization of water-soluble macrocyclic peptides stabilizing protein α-turn


Lei Wang, Pascale Coric, Kexin Zhu, Wang-Qing Liu, Michel Vidal, Serge Bouaziz and Sylvain Broussy
Org. Biomol. Chem., 2018,16, 459-471
From themed collection: Chemical biology in OBC

Abstract

Macrocyclic peptides mimic tight “non-classical” α-turn type II-αLS found in proteins, as shown by spectroscopic and computational analysis of their equilibrating conformations.


Stereocontrolled glycoside synthesis by activation of glycosyl sulfone donors with scandium(III) triflate


Amandine Xolin, Romain Losa, Aicha Kaid, Cédric Tresse, Jean-Marie Beau, François-Didier Boyer and Stéphanie Norsikian
Org. Biomol. Chem., 2018,16, 325-335
From themed collection: Chemical biology in OBC

Abstract

Activation of armed glycosyl sulfone donors, using scandium(III) triflate under microwave irradiation, provides a selective preparation of α-mannosides.


Synthesis and structural investigation of a series of mannose-containing oligosaccharides using mass spectrometry


S. Daikoku, R. Pendrill, Y. Kanie, Y. Ito, G. Widmalm and O. Kanie
Org. Biomol. Chem., 2018,16, 228-238
From themed collection: Chemical biology in OBC

Abstract

Gas-phase collision-induced dissociation and acid hydrolysis of mannose-containing oligosaccharides were performed, which revealed the reactivity order of linkage isomers.


Side chain-specific 11/9-helix propensity of α/β-peptides with alternating residue types


Jaeyeon Lee, Jihyun Shim, Philjae Kang, Moon-Gun Choi and Soo Hyuk Choi
Org. Biomol. Chem., 2018,16, 433-438
From themed collection: Chemical biology in OBC

Abstract

The 11/9-helix propensity of α/β-peptides is dependent on a specific side chain group of α- or β3-residue.


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Macrocyclization of an all-D linear α-helical peptide imparts cellular permeability


Srinivasaraghavan Kannan, Pietro G. A. Aronica, Simon Ng, Dawn Thean Gek Lian, Yuri Frosi, Sharon Chee, Jiang Shimin, Tsz Ying Yuen, Ahmad Sadruddin, Hung Yi Kristal Kaan, Arun Chandramohan, Jin Huei Wong, Yaw Sing Tan, Zi Wei Chang, Fernando J. Ferrer-Gago, Prakash Arumugam, Yi Han, Shiying Chen, Laurent Rénia, Christopher J. Brown, Charles W. Johannes, Brian Henry, David P. Lane, Tomi K. Sawyer, Chandra S. Verma and Anthony W. Partridge
Chem. Sci., 2020,11, 5577-5591

Abstract

Peptide-based molecules hold great potential as targeted inhibitors of intracellular protein–protein interactions (PPIs).


General dual functionalisation of biomacromolecules via a cysteine bridging strategy


Stephen J. Walsh, Jessica Iegre, Hikaru Seki, Jonathan D. Bargh, Hannah F. Sore, Jeremy S. Parker, Jason S. Carroll and David R. Spring
Org. Biomol. Chem., 2020,18, 4224-4230
From themed collection: Methodology development for protein modifications

Abstract

A general method that facilitates the modular dual functionalisation of a range of peptides and proteins is reported.


Gs protein peptidomimetics as allosteric modulators of the β2-adrenergic receptor


Lotte-Emilie Boyhus, Mia Danielsen, Nina Smidt Bengtson, Micha Ben Achim Kunze, Xavier Kubiak, Tjerk J. Sminia, Jacob Hartvig Løper, Phuong Thu Tran, Kresten Lindorff-Larsen, Søren G. F. Rasmussen, Jesper Mosolff Mathiesen and Daniel Sejer Pedersen
RSC Adv., 2018,8, 2219-2228
From themed collection: Editors' collection: Chemical Biology

Abstract

A series of Gs protein peptidomimetics were designed and synthesised based on the published X-ray crystal structure of the active state β2-adrenergic receptor (β2AR) in complex with the Gs protein (PDB 3SN6).


Construction of histidine-containing hydrocarbon stapled cell penetrating peptides for in vitro and in vivo delivery of siRNAs


Soonsil Hyun, Yoonhwa Choi, Ha Neul Lee, Changki Lee, Donghoon Oh, Dong-Ki Lee, Changjin Lee, Yan Lee and Jaehoon Yu
Chem. Sci., 2018,9, 3820-3827

Abstract

A hydrocarbon stapled peptide, LKH-stEK, promotes delivery of nanomolar siRNAs leading to efficient gene silencing in mouse skin.


Structural insights reveal a recognition feature for tailoring hydrocarbon stapled-peptides against the eukaryotic translation initiation factor 4E protein


Dilraj Lama, Anne-Marie Liberatore, Yuri Frosi, Jessica Nakhle, Natia Tsomaia, Tarig Bashir, David P. Lane, Christopher J. Brown, Chandra S. Verma and Serge Auvin
Chem. Sci., 2019,10, 2489-2500

Abstract

We have revealed a non-canonical recognition feature that can modulate the binding kinetics of hydrocarbon stapled-peptides interactions with the eIF4E protein.


CHAPTER 11
Development of Peptide-Based Diagnostic and Therapeutic Agents in Oncology


Kamala Kesavan
Peptide-based Drug Discovery: Challenges and New Therapeutics, 2017, 326-363

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