scholarly journals Peptide Stapling with Anion‐π Catalysts

2020 ◽  
Vol 15 (10) ◽  
pp. 1562-1566
Author(s):  
Anh‐Tuan Pham ◽  
Stefan Matile
Keyword(s):  
Peptide Stapling

Diversity-Oriented Peptide Stapling: A Third Generation Copper-Catalysed Azide-Alkyne Cycloaddition Stapling and Functionalisation Strategy

2017 ◽  
Vol 23 (14) ◽  
pp. 3490-3495 ◽  
Author(s):  
Phuong Thu Tran ◽  
Christian Ørnbøl Larsen ◽  
Tobias Røndbjerg ◽  
Martina De Foresta ◽  
Micha B. A. Kunze ◽  
...  
Keyword(s):  
Third Generation ◽  
Peptide Stapling

scholarly journals A Physical Organic Approach to Tuning Reagents for Selective and Stable Methionine Bioconjugation

2019 ◽  
Author(s):  
Alec Christian ◽  
Shang Jia ◽  
Patricia Zhang ◽  
Arismel Tena Meza ◽  
Matthew S. Sigman ◽  
...  
Keyword(s):  
Structural Features ◽  
Data Driven ◽  
Live Cells ◽  
Design And Synthesis ◽  
Use Of Data ◽  
Physical Organic ◽  
Driving Stability ◽  
Peptide Stapling ◽  
Insight Into ◽  
Unique Chemical

We report a data-driven, physical organic approach to the development of new methionine-selective bioconjugation reagents with tunable adduct stabilities. Statistical modeling of structural features described by intrinsic physical organic parameters was applied to the development of a predictive model and to gain insight into features driving stability of adducts formed from the chemoselective coupling of oxaziridine and methionine thioether partners through Redox Activated Chemical Tagging (ReACT). From these analyses, a correlation between sulfimide stabilities and sulfimide  (C=O) stretching frequencies was revealed. We ex-ploited the rational gains in adduct stability exposed by this analysis to achieve the design and synthesis of a bis-oxaziridine reagent for peptide stapling. Indeed, we observed that a macrocyclic peptide formed by ReACT stapling at methionine exhibited improved uptake into live cells compared to an unstapled congener, highlighting the potential utility of this unique chemical tool for thioether modification. This work provides a template for the broader use of data-driven approaches to bioconjugation chemistry and other chemical biology applications.

Direct Synthesis of N-Functionalized Dipropargylamine Linkers as Models for Use in Peptide Stapling

Synlett ◽  
2019 ◽  
Vol 30 (19) ◽  
pp. 2153-2156
Author(s):  
Andrea Renzetti ◽  
Ryan N. Rutherford ◽  
Kozo Fukumoto ◽  
Dominique Kunciw ◽  
Hannah F. Sore ◽  
...  
Keyword(s):  
Direct Synthesis ◽  
Quantitative Yield ◽  
Mild Conditions ◽  
One Step ◽  
Peptide Stapling

N-Substituted dipropargylamines that are suitable as functionalized linkers for peptide stapling can be synthesized in one step under mild conditions from commercially available starting materials (41% to quantitative yield).

Robust asymmetric synthesis of unnatural alkenyl amino acids for conformationally constrained α-helix peptides

2014 ◽  
Vol 12 (43) ◽  
pp. 8775-8782 ◽  
Author(s):  
Boris Aillard ◽  
Naomi S. Robertson ◽  
Adam R. Baldwin ◽  
Siobhan Robins ◽  
Andrew G. Jamieson
Keyword(s):  
Amino Acids ◽  
Schiff Base ◽  
Asymmetric Synthesis ◽  
Schiff Base Complex ◽  
Conformationally Constrained ◽  
Base Complex ◽  
Α Helix ◽  
Peptide Stapling

The efficient asymmetric synthesis of unnatural alkenyl amino acids required for peptide ‘stapling’ has been achieved using alkylation of a fluorine-modified NiII Schiff base complex as the key step.

scholarly journals Variations on peptide stapling using PEG

2020 ◽  
Author(s):  
Dallin Ashton ◽  
Qiang Xiao ◽  
Joshua L Price
Keyword(s):  
Peptide Stapling

scholarly journals Structural optimization of reversible dibromomaleimide peptide stapling

2020 ◽  
pp. e24157 ◽  
Author(s):  
Ayanna Lindsey-Crosthwait ◽  
Diana Rodriguez-Lema ◽  
Martin Walko ◽  
Christopher M. Pask ◽  
Andrew J. Wilson
Keyword(s):  
Structural Optimization ◽  
Peptide Stapling

scholarly journals Development of a Multifunctional Benzophenone Linker for Peptide Stapling and Photoaffinity Labelling

ChemBioChem ◽  
2016 ◽  
Vol 17 (8) ◽  
pp. 689-692 ◽  
Author(s):  
Yuteng Wu ◽  
Lasse B. Olsen ◽  
Yu Heng Lau ◽  
Claus Hatt Jensen ◽  
Maxim Rossmann ◽  
...  
Keyword(s):  
Photoaffinity Labelling ◽  
Peptide Stapling

scholarly journals Bioinspired Nitroalkylation for Selective Protein Modification and Peptide Stapling

2020 ◽  
Vol 59 (7) ◽  
pp. 2793-2801 ◽  
Author(s):  
Sriram Mahesh ◽  
Victor Adebomi ◽  
Zilma P. Muneeswaran ◽  
Monika Raj
Keyword(s):  
Protein Modification ◽  
Peptide Stapling
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