scholarly journals Multifunctional and Transformable ‘Clickable’ Hydrogel Coatings on Titanium Surfaces: From Protein Immobilization to Cellular Attachment

Polymers ◽  
2020 ◽  
Vol 12 (6) ◽  
pp. 1211
Author(s):  
Tugce Nihal Gevrek ◽  
Aysun Degirmenci ◽  
Rana Sanyal ◽  
Amitav Sanyal
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Click Reactions ◽  
Ene Reaction ◽  
Diels Alder Reaction ◽  
Cellular Attachment ◽  
Wide Range ◽  
Hydrogel Coatings ◽  
Titanium Surfaces ◽  
Maleimide Group

Multifunctionalizable hydrogel coatings on titanium interfaces are useful in a wide range of biomedical applications utilizing titanium-based materials. In this study, furan-protected maleimide groups containing multi-clickable biocompatible hydrogel layers are fabricated on a titanium surface. Upon thermal treatment, the masked maleimide groups within the hydrogel are converted to thiol-reactive maleimide groups. The thiol-reactive maleimide group allows facile functionalization of these hydrogels through the thiol-maleimide nucleophilic addition and Diels–Alder cycloaddition reactions, under mild conditions. Additionally, the strained alkene unit in the furan-protected maleimide moiety undergoes radical thiol-ene reaction, as well as the inverse-electron-demand Diels–Alder reaction with tetrazine containing molecules. Taking advantage of photo-initiated thiol-ene ‘click’ reactions, we demonstrate spatially controlled immobilization of the fluorescent dye thiol-containing boron dipyrromethene (BODIPY-SH). Lastly, we establish that the extent of functionalization on hydrogels can be controlled by attachment of biotin-benzyl-tetrazine, followed by immobilization of TRITC-labelled ExtrAvidin. Being versatile and practical, we believe that the described multifunctional and transformable ‘clickable’ hydrogels on titanium-based substrates described here can find applications in areas involving modification of the interface with bioactive entities.

Reactions of Dimethyl (2'-Oxopropylidene)Propanedioate and Dimethyl (3'-Bromo-2'-oxopropylidene)propanedioate, Two Highly Electrophilic Trisubstituted Alkenes

1987 ◽  
Vol 40 (11) ◽  
pp. 1831 ◽  
Author(s):  
DW Cameron ◽  
RW Read ◽  
J Stavrakis
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Low Molecular Weight ◽  
Ene Reaction ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Alkaline Conditions ◽  
Nucleophilic Reagents ◽  
Trisubstituted Alkenes ◽  
Electron Demand

The keto diester, dimethyl (2'-oxopropylidene)propanedioate, and its new 3'-bromo derivative have been made to react with a variety of nucleophilic reagents. Low molecular weight products have been obtained efficiently by processes involving conjugate addition, Diels-Alder reaction, Diels-Alder reaction having inverse electron demand, or ene reaction. Regiochemistry of the reactions is controlled by the dominant withdrawing effect of the two geminal ester groups. The amine addition products of the bromo keto diester were found to undergo a novel secondary dehydrobromination reaction under alkaline conditions.

scholarly journals Cover Feature: Hetero Diels-Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis (Eur. J. Org. Chem. 45/2018)

2018 ◽  
Vol 2018 (45) ◽  
pp. 6192-6192
Author(s):  
Saki Uraoka ◽  
Ikumi Shinohara ◽  
Hisato Shimizu ◽  
Keiichi Noguchi ◽  
Akira Yoshimura ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Ene Reaction ◽  
Diels Alder Reaction

scholarly journals Quantum Mechanical Modeling Unveil the Effect of Substitutions on the Activation Barriers of the Diels-Alder Reactions of an Antiviral Compound 7H-Benzo[a]phenalene

2021 ◽  
Author(s):  
Umatur Rehman ◽  
Asim Mansha ◽  
Muhammad Zahid ◽  
Sadia Asim ◽  
Ameer Fawad Zahoor ◽  
...  
Keyword(s):  
Maleic Anhydride ◽  
Density Functional ◽  
Activation Barrier ◽  
Experimental Studies ◽  
Alder Reaction ◽  
Diels Alder ◽  
Antiviral Compound ◽  
Fukui Functions ◽  
Diels Alder Reaction ◽  
Wide Range

Abstract Density functional theory has been utilized for exploring the mechanism of Diels-Alder reaction between 7H-benzo[a]phenalene and maleic anhydride. 7H-Benzo[a]phenalene is an antiviral compound and information available about its cycloaddition reactions with possible reaction path and mechanism is scarce. In order to work on the synthesis of its further potential derivatives, the mechanism of its reaction with all aspects should be well understood. Two novel intermediates involved in this reaction have been reported. Diels-Alder reaction of maleic anhydride has found many applications in the synthesis of wide range of useful products. The major concern of this work is to evaluate the consequences of introducing electron donating and electron withdrawing substituents on the reactivity of maleic anhydride towards 7H-benzo[a]phenalene. Thermodynamic parameters, activation parameters, energies of frontier orbitals, global reactivity indices and global electron density transfer (GEDT) have been determined for all the reactions. Fukui functions are computed for each reactant in order to identify the most reactive sites. All the reactions have been found to proceed via normal electron demand having polar nature. The substituents with opposite electronic properties were expected to affect the reactivity of dienophile in an inverse manner, however, the results are not according to this assumption. Rather, both kinds of substituents increased the activation barrier of the reaction. This behavior has been explained in the light of various parameters such as the stability of reacting species, gap of frontier molecular orbitals etc. Experimental studies reported previously are in agreement with these results.

Hetero Diels-Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis

2018 ◽  
Vol 2018 (45) ◽  
pp. 6199-6203 ◽  
Author(s):  
Saki Uraoka ◽  
Ikumi Shinohara ◽  
Hisato Shimizu ◽  
Keiichi Noguchi ◽  
Akira Yoshimura ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Ene Reaction ◽  
Diels Alder Reaction

scholarly journals Biomimetic Total Synthesis of (+)-Chloropupukeananin, (–)-Chloropupukeanolide D, and Chloropestolides

2021 ◽  
Author(s):  
Takahiro Suzuki ◽  
Soichiro Watanabe ◽  
Wataru Ikeda ◽  
Susumu Kobayashi ◽  
Keiji Tanino
Keyword(s):  
Total Synthesis ◽  
Solvent Effect ◽  
Alder Reaction ◽  
Diels Alder ◽  
Biomimetic Synthesis ◽  
Ene Reaction ◽  
Diels Alder Reaction

The biomimetic total synthesis of (+)-chloropupukeananin (overall 4.5% yield, 19 steps from pyrone <b>22</b>) and (−)-chloropupukeanolide D via an intermolecular Diels-Alder reaction using (−)-maldoxin and (+)-iso-A82775C and an intramolecular carbonyl-ene reaction has been achieved. Moreover, the biomimetic synthesis of chloropestolides H-K using (−)-maldoxin and siccayne unveiled the solvent effect of the intermolecular Diels-Alder reaction. The origin of the stereoselectivity of the intermolecular Diels-Alder reaction is still elusive; however, the biosynthesis of the chloropupukeananin family should involve enzymes that catalyse the intermolecular Diels-Alder reaction.

Site-specific one-pot triple click labeling for DNA and RNA

2018 ◽  
Vol 54 (83) ◽  
pp. 11781-11784 ◽  
Author(s):  
Marie-Luise Winz ◽  
Eva Christina Linder ◽  
Juliane Becker ◽  
Andres Jäschke
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Site Specific ◽  
Click Reactions ◽  
Inverse Electron Demand ◽  
Dna And Rna ◽  
Diels Alder Reaction ◽  
Electron Demand

We report site-specific triple click labeling for DNA and RNA in a one-pot setup by performing inverse electron demand Diels–Alder reaction and strain-promoted and copper catalyzed click reactions sequentially.

scholarly journals Biomimetic Total Synthesis of (+)-Chloropupukeananin, (–)-Chloropupukeanolide D, and Chloropestolides

2021 ◽  
Author(s):  
Takahiro Suzuki ◽  
Soichiro Watanabe ◽  
Wataru Ikeda ◽  
Susumu Kobayashi ◽  
Keiji Tanino
Keyword(s):  
Total Synthesis ◽  
Solvent Effect ◽  
Alder Reaction ◽  
Diels Alder ◽  
Biomimetic Synthesis ◽  
Ene Reaction ◽  
Diels Alder Reaction

The biomimetic total synthesis of (+)-chloropupukeananin (overall 4.5% yield, 19 steps from pyrone <b>22</b>) and (−)-chloropupukeanolide D via an intermolecular Diels-Alder reaction using (−)-maldoxin and (+)-iso-A82775C and an intramolecular carbonyl-ene reaction has been achieved. Moreover, the biomimetic synthesis of chloropestolides H-K using (−)-maldoxin and siccayne unveiled the solvent effect of the intermolecular Diels-Alder reaction. The origin of the stereoselectivity of the intermolecular Diels-Alder reaction is still elusive; however, the biosynthesis of the chloropupukeananin family should involve enzymes that catalyse the intermolecular Diels-Alder reaction.

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