Receptor-templated stapling of intrinsically disordered peptide ligands

Organic & Biomolecular Chemistry
Conor M Haney, W Seth Horne

Abstract

We report here a chemoselective peptide "stapling" method that can be performed on ligand-receptor complexes in situ. An appropriately structured macrocyclic bis-oxime linkage is shown to improve the affinity of a peptide ligand for its native protein receptor. The presence of the receptor as a template to preorganize the ligand into its bioactive conformation is found to bias reaction outcomes, suggesting the potential application of the method for receptor-assisted selection of stapled peptides.

References

Nov 1, 1989·Analytical Biochemistry·S C Gill, P H von Hippel
May 22, 1997·Nature·W WeissenhornD C Wiley
Nov 14, 1997·Proceedings of the National Academy of Sciences of the United States of America·K TanM Lu
Feb 12, 1998·Proceedings of the National Academy of Sciences of the United States of America·J K JudiceR S McDowell
Dec 23, 1998·Proceedings of the National Academy of Sciences of the United States of America·D C ChanP S Kim
Nov 6, 2002·Proceedings of the National Academy of Sciences of the United States of America·Samuel K SiaPeter S Kim
Jul 23, 2003·Biochimica Et Biophysica Acta·Stephen A GalloRobert Blumenthal
Sep 10, 2003·Proceedings of the National Academy of Sciences of the United States of America·John P Moore, Robert W Doms
Mar 20, 2004·Nature Reviews. Drug Discovery·Tom MatthewsDani Bolognesi
May 19, 2005·Chemical Communications : Chem Comm·Florence M Brunel, Philip E Dawson
Sep 12, 2006·Proceedings of the National Academy of Sciences of the United States of America·Gary FreyStephen C Harrison
Feb 8, 2007·Journal of the American Chemical Society·Federico BernalGregory L Verdine
Jul 21, 2007·Proceedings of the National Academy of Sciences of the United States of America·John J DwyerMary K Delmedico
Oct 27, 2007·Journal of the American Chemical Society·Fuzhong ZhangG Andrew Woolley
Jan 29, 2008·Angewandte Chemie·Deyun WangParamjit S Arora
Feb 24, 2009·Nature Methods·Ying ZengJames C Paulson
Aug 27, 2009·Proceedings of the National Academy of Sciences of the United States of America·W Seth HorneSamuel H Gellman
Jul 28, 2010·Proceedings of the National Academy of Sciences of the United States of America·Gregory H BirdLoren D Walensky
Dec 23, 2010·Journal of the American Chemical Society·Masaoki KajinoMasahiko Inouye
Jun 22, 2011·Chemical Communications : Chem Comm·Conor M HaneyW Seth Horne
Jun 24, 2011·Nature Chemistry·Christopher J White, Andrei K Yudin
Sep 24, 2011·Expert Opinion on Biological Therapy·Glenn F King
Jan 11, 2012·Methods in Enzymology·Gregory L Verdine, Gerard J Hilinski
Jan 11, 2012·Methods in Enzymology·Richard J Clark, David J Craik
Aug 28, 2012·Journal of the American Chemical Society·Avinash MuppidiQing Lin
Sep 25, 2012·Journal of the American Chemical Society·Hyunil JoDoron C Greenbaum
Dec 12, 2012·ACS Chemical Biology·Christopher J BrownDavid P Lane
Feb 21, 2013·Nature Chemistry·Valeria AzzaritoAndrew J Wilson
Apr 9, 2013·Journal of the American Chemical Society·Alexander M SpokoynyBradley L Pentelute
Dec 7, 2013·Organic & Biomolecular Chemistry·Yekui ZouBradley L Pentelute
Jan 10, 2014·Journal of Peptide Science : an Official Publication of the European Peptide Society·Conor M Haney, W Seth Horne
Dec 17, 1998·Angewandte Chemie·Helen E Blackwell, Robert H Grubbs

❮ Previous
Next ❯

Citations

Jun 1, 2016·Chemical Science·Jennifer A MilesAndrew J Wilson

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.