scholarly journals Pyrroloindole-Based Dynamic Combinatorial Chemistry

Symmetry ◽  
2020 ◽  
Vol 12 (5) ◽  
pp. 726
Author(s):  
Tiberiu-Marius Gianga ◽  
Dora-Maria Răsădean ◽  
G. Dan Pantoș
Keyword(s):  
Ionic Strength ◽  
Combinatorial Chemistry ◽  
Building Block ◽  
Combinatorial Libraries ◽  
Building Blocks ◽  
Disulfide Exchange ◽  
Dynamic Combinatorial Chemistry ◽  
New Class ◽  
The Core

We report a new class of building blocks for Dynamic Combinatorial Chemistry (DCC) based on the pyrroloindole scaffold. The attachment of l-cysteine on the α, α′ positions of the core makes the molecule suitable for disulfide exchange in aqueous dynamic combinatorial libraries (DCLs). The synthesis of the core follows a modified version of the Knoevenagel–Hemetsberger approach. The new building block (l-PI) is fluorescent (Φ = 48%) and relatively stable towards thermal and photodegradation. The chirality of the cysteine is transferred to the electron-rich pyrroloindole core. Homo- and heterochiral DCLs of l-PI with electron-deficient l- and d-naphthalenediimide (NDI) lead to similar library distributions regardless of the enantiomer used. When no salt is present, the major component is a dimer, while dimers and tetramers are obtained at increased ionic strength.

scholarly journals Adventures in molecular recognition. The ins and outs of templating

2000 ◽  
Vol 72 (12) ◽  
pp. 2265-2274 ◽  
Author(s):  
Jeremy K. M. Sanders
Keyword(s):  
Molecular Recognition ◽  
Combinatorial Chemistry ◽  
Biological Systems ◽  
Design Approach ◽  
Supramolecular Systems ◽  
Disulfide Exchange ◽  
Dynamic Combinatorial Chemistry ◽  
Evolutionary Features ◽  
Selection Approach ◽  
Porphyrin Dimers

Two different approaches are described for the creation of supramolecular systems potentially capable of recognition and catalysis. Using the design approach, we have been able to accelerate and influence two different Diels­Alder reactions within the cavities of porphyrin dimers and trimers; this is templating from the outside inwards. The selection approach is a synthetic chemical attempt to capture some of the key evolutionary features of biological systems: dynamic combinatorial chemistry is used to create equilibrating mixtures of potential receptors, and then a template is used to select and amplify the desired system. Five potential reactions for such dynamic chemistry are discussed: base-catalyzed transesterification, hydrazone exchange, disulfide exchange, alkene metathesis, and Pd-catalyzed allyl exchange, and preliminary templating results (inside outwards) are presented.

scholarly journals The dark side of disulfide-based dynamic combinatorial chemistry

2020 ◽  
Vol 11 (31) ◽  
pp. 8151-8156
Author(s):  
Mélissa Dumartin ◽  
Jean Septavaux ◽  
Marion Donnier-Maréchal ◽  
Emeric Jeamet ◽  
Elise Dumont ◽  
...  
Keyword(s):  
Combinatorial Chemistry ◽  
Combinatorial Libraries ◽  
Dark Side ◽  
Dynamic Combinatorial Chemistry ◽  
Analytical Tools

We show that multiple analytical tools are necessary in order to describe the different phenomena within disulfide-based dynamic combinatorial libraries in terms of size, stereochemistry, affinity and selectivity.

scholarly journals Biomimetic selenocystine based dynamic combinatorial chemistry for thiol-disulfide exchange

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Andrea Canal-Martín ◽  
Ruth Pérez-Fernández
Keyword(s):  
Glucose Oxidase ◽  
Combinatorial Chemistry ◽  
Self Assembly ◽  
Equilibrium Composition ◽  
Competitive Inhibitor ◽  
Rnase A ◽  
Disulfide Exchange ◽  
Dynamic Combinatorial Chemistry ◽  
Physiological Conditions ◽  
Ph Conditions

AbstractDynamic combinatorial chemistry applied to biological environments requires the exchange chemistry of choice to take place under physiological conditions. Thiol-disulfide exchange, one of the most popular dynamic combinatorial chemistries, usually needs long equilibration times to reach the required equilibrium composition. Here we report selenocystine as a catalyst mimicking Nature’s strategy to accelerate thiol-disulfide exchange at physiological pH and low temperatures. Selenocystine is able to accelerate slow thiol-disulfide systems and to promote the correct folding of an scrambled RNase A enzyme, thus broadening the practical range of pH conditions for oxidative folding. Additionally, dynamic combinatorial chemistry target-driven self-assembly processes are tested using spermine, spermidine and NADPH (casting) and glucose oxidase (molding). A non-competitive inhibitor is identified in the glucose oxidase directed dynamic combinatorial library.

Dynamic combinatorial chemistry with hydrazones: cholate-based building blocks and libraries

2010 ◽  
Vol 8 (5) ◽  
pp. 1173 ◽  
Author(s):  
Mark G. Simpson ◽  
Michael Pittelkow ◽  
Stephen P. Watson ◽  
Jeremy K. M. Sanders
Keyword(s):  
Combinatorial Chemistry ◽  
Building Blocks ◽  
Dynamic Combinatorial Chemistry

Optimization of a synthetic receptor for dimethyllysine using a biphenyl-2,6-dicarboxylic acid scaffold: insights into selective recognition of hydrophilic guests in water

2017 ◽  
Vol 15 (37) ◽  
pp. 7789-7795 ◽  
Author(s):  
Isaiah N. Gober ◽  
Marcey L. Waters
Keyword(s):  
Dicarboxylic Acid ◽  
Combinatorial Chemistry ◽  
Building Block ◽  
Selective Recognition ◽  
Post Translational Modification ◽  
New Host ◽  
Dynamic Combinatorial Chemistry ◽  
Synthetic Receptor

Introduction of an endo-carboxylate in a building block for dynamic combinatorial chemistry resulted in amplification of a new host with a Kd of 200 nM for dimethyllysine, a biologically important post-translational modification.

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