Singlet oxygen-mediated one-pot chemoselective peptide–peptide ligation

2017 ◽  
Vol 15 (38) ◽  
pp. 8140-8144 ◽  
Author(s):  
Eirini Antonatou ◽  
Yentl Verleysen ◽  
Annemieke Madder
Keyword(s):  
Singlet Oxygen ◽  
One Pot ◽  
Specific Chemical ◽  
Chemical Ligation ◽  
Site Specific ◽  
Peptide Segments ◽  
Peptide Ligation

We here describe a furan oxidation based site-specific chemical ligation approach using unprotected peptide segments.

scholarly journals Singlet Oxygen-Induced Furan Oxidation for Site-Specific and Chemoselective Peptide Ligation

2016 ◽  
Vol 22 (25) ◽  
pp. 8457-8461 ◽  
Author(s):  
Eirini Antonatou ◽  
Kurt Hoogewijs ◽  
Dimitris Kalaitzakis ◽  
Andreas Baudot ◽  
Georgios Vassilikogiannakis ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Site Specific ◽  
Peptide Ligation

scholarly journals Thiazolidine Deprotection by 2-Aminobenzamide-Based Aldehyde Scavenger for One-Pot Multiple Peptide Ligation

2021 ◽  
Author(s):  
Koki Nakatsu ◽  
Hitoshi Murakami ◽  
Gosuke Hayashi ◽  
Akimitsu Okamoto
Keyword(s):  
Native Chemical Ligation ◽  
High Yield ◽  
Side Reactions ◽  
Model Peptide ◽  
One Pot ◽  
Chemical Ligation ◽  
Good Ability ◽  
Synthetic Proteins ◽  
Short Time ◽  
Peptide Ligation

Strategies for one-pot peptide ligation enable chemists to access synthetic proteins at a high yield in a short time. Herein, we report a new one-pot multi-segments ligation strategy using N-terminal thiazolidine (Thz) peptide and a formaldehyde scavenger. Among our designed 2-aminobenzamide-based aldehyde scavengers, 2-amino-5-methoxy-N’,N’-dimethylbenzohydrazide showed a good ability to capture formaldehyde from Thz at pH 4.0. This scavenger had compatibility with the conditions of native chemical ligation at pH 7.5. Using this scavenger for a model peptide ligation system, we performed one-pot four-segment ligation at a high yield without significant side reactions.

One-pot native chemical ligation by combination of two orthogonal thioester precursors

2017 ◽  
Vol 53 (13) ◽  
pp. 2114-2117 ◽  
Author(s):  
Yuya Asahina ◽  
Toru Kawakami ◽  
Hironobu Hojo
Keyword(s):  
Native Chemical Ligation ◽  
Protecting Group ◽  
One Pot ◽  
Chemical Ligation ◽  
Ligation Reaction ◽  
Ligation Method ◽  
Peptide Ligation

We developed a one-pot peptide ligation method using two orthogonal thioester precursors and a protecting group for the ligation reaction between Asp and Cys.

scholarly journals Thiazolidine Deprotection by 2-Aminobenzamide-Based Aldehyde Scavenger for One-Pot Multiple Peptide Ligation

2021 ◽  
Author(s):  
Koki Nakatsu ◽  
Hitoshi Murakami ◽  
Gosuke Hayashi ◽  
Akimitsu Okamoto
Keyword(s):  
Native Chemical Ligation ◽  
High Yield ◽  
Side Reactions ◽  
Model Peptide ◽  
One Pot ◽  
Chemical Ligation ◽  
Good Ability ◽  
Synthetic Proteins ◽  
Short Time ◽  
Peptide Ligation

Strategies for one-pot peptide ligation enable chemists to access synthetic proteins at a high yield in a short time. Herein, we report a new one-pot multi-segments ligation strategy using N-terminal thiazolidine (Thz) peptide and a formaldehyde scavenger. Among our designed 2-aminobenzamide-based aldehyde scavengers, 2-amino-5-methoxy-N’,N’-dimethylbenzohydrazide showed a good ability to capture formaldehyde from Thz at pH 4.0. This scavenger had compatibility with the conditions of native chemical ligation at pH 7.5. Using this scavenger for a model peptide ligation system, we performed one-pot four-segment ligation at a high yield without significant side reactions.

Reactive Nanopattern in a Triple Structured Bio-Inspired Honeycomb Film as a Clickable Platform

2018 ◽  
Author(s):  
Pierre Marcasuzaa ◽  
Samuel Pearson ◽  
Karell Bosson ◽  
Laurence Pessoni ◽  
Jean-Charles Dupin ◽  
...  
Keyword(s):  
Self Assembly ◽  
Double Porosity ◽  
Surface Groups ◽  
Specific Chemical ◽  
Site Specific ◽  
Surface Functionality ◽  
Wenzel State ◽  
Breath Figure ◽  
Responsive Surfaces ◽  
Secondary Population

A hierarchically structured platform was obtained from spontaneous self-assembly of a poly(styrene)-<i>b</i>-poly(vinylbenzylchloride) (PS-<i>b</i>-PVBC) block copolymer (BCP) during breath figure (BF) templating. The BF process using a water/ethanol atmosphere gave a unique double porosity in which hexagonally arranged micron-sized pores were encircled by a secondary population of smaller, nano-sized pores. A third level of structuration was simultaneously introduced between the pores by directed BCP self-assembly to form out-of-the-plane nano-cylinders, offering very rapid bottom-up access to a film with unprecedented triple structure which could be used as a reactive platform for introducing further surface functionality. The surface nano-domains of VBC were exploited as reactive nano-patterns for site-specific chemical functionalization by firstly substituting the exposed chlorine moiety with azide, then “clicking” an alkyne by copper (I) catalyzed azide-alkyne Huisgen cycloaddition (CuAAC). Successful chemical modification was verified by NMR spectroscopy, FTIR spectroscopy, and XPS, with retention of the micro- and nanostructuration confirmed by SEM and AFM respectively. Protonation of the cyclotriazole surface groups triggered a switch in macroscopic behavior from a Cassie-Baxter state to a Wenzel state, highlighting the possibility of producing responsive surfaces with hierarchical structure.

IL-4 Analogues with Site-Specific Chemical Modification at Position 121 Inhibit IL-4 and IL-13 Biological Activities

2013 ◽  
Vol 25 (1) ◽  
pp. 52-62 ◽  
Author(s):  
Viswanadham Duppatla ◽  
Maja Gjorgjevikj ◽  
Werner Schmitz ◽  
Heike M. Hermanns ◽  
Carmen M. Schäfer ◽  
...  
Keyword(s):  
Chemical Modification ◽  
Biological Activities ◽  
Specific Chemical ◽  
Site Specific ◽  
Specific Chemical Modification

scholarly journals Controlling activation of the RNA-dependent protein kinase by siRNAs using site-specific chemical modification

2006 ◽  
Vol 34 (17) ◽  
pp. 4900-4911 ◽  
Author(s):  
Sujiet Puthenveetil ◽  
Landon Whitby ◽  
Jin Ren ◽  
Kevin Kelnar ◽  
Joseph F. Krebs ◽  
...  
Keyword(s):  
Protein Kinase ◽  
Chemical Modification ◽  
Dependent Protein Kinase ◽  
Specific Chemical ◽  
Site Specific ◽  
Specific Chemical Modification ◽  
Dependent Protein
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