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Literature DB >> 29512665

Multifunctional monomers based on vinyl sulfonates and vinyl sulfonamides for crosslinking thiol-Michael polymerizations: monomer reactivity and mechanical behavior.

Jasmine Sinha¹, Maciej Podgórski², Sijia Huang¹, Christopher N Bowman¹.

Abstract

Multifunctional vinyl sulfonates and vinyl sulfonamides were conveniently synthesized and assessed in thiol-Michael crosslinking polymerizations. The monomer reactivities, mechanical behavior and hydrolytic properties were analyzed and compared with those of analogous thiol-acrylate polymerizations. Materials with a broad range of mechanical properties and diverse hydrolytic stabilities were obtained.

Entities: CellLine Chemical Gene

Year: 2018 PMID： 29512665 PMCID： PMC5875713 DOI： 10.1039/c8cc00782a

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

9 in total

1. Vinyl sulfone: a versatile function for simple bioconjugation and immobilization.

Authors: Julia Morales-Sanfrutos; Javier Lopez-Jaramillo; Mariano Ortega-Muñoz; Alicia Megia-Fernandez; Francisco Perez-Balderas; Fernando Hernandez-Mateo; Francisco Santoyo-Gonzalez
Journal: Org Biomol Chem Date: 2009-12-11 Impact factor: 3.876

Review 2. Developments and recent advancements in the field of endogenous amino acid selective bond forming reactions for bioconjugation.

Authors: Oleksandr Koniev; Alain Wagner
Journal: Chem Soc Rev Date: 2015-05-22 Impact factor: 54.564

3. Ester-free Thiol-X Resins: New Materials with Enhanced Mechanical Behavior and Solvent Resistance.

Authors: Maciej Podgórski; Eftalda Becka; Shunsuke Chatani; Mauro Claudino; Christopher N Bowman
Journal: Polym Chem Date: 2015 Impact factor: 5.582

4. Azidopropylvinylsulfonamide as a New Bifunctional Click Reagent for Bioorthogonal Conjugations: Application for DNA-Protein Cross-Linking.

Authors: Jitka Dadová; Milan Vrábel; Matej Adámik; Marie Brázdová; Radek Pohl; Miroslav Fojta; Michal Hocek
Journal: Chemistry Date: 2015-09-17 Impact factor: 5.236

5. Synthesis and anti-HIV-1 activity of a novel series of 1,4,2-benzodithiazine-dioxides.

Authors: Zdzisław Brzozowski; Franciszek Saczewski; Nouri Neamati
Journal: Bioorg Med Chem Lett Date: 2006-08-14 Impact factor: 2.823

6. Synthesis of functionalized sulfonamides via 1,3-dipolar cycloaddition of pentafluorophenyl vinylsulfonate.

Authors: Stephen Caddick; Hannah D Bush
Journal: Org Lett Date: 2003-07-10 Impact factor: 6.005

7. Development of glassy step-growth thiol-vinyl sulfone polymer networks.

Authors: Maciej Podgórski; Shunsuke Chatani; Christopher N Bowman
Journal: Macromol Rapid Commun Date: 2014-06-25 Impact factor: 5.734

8. Relative rates of Michael reactions of 2'-(phenethyl)thiol with vinyl sulfones, vinyl sulfonate esters, and vinyl sulfonamides relevant to vinyl sulfonyl cysteine protease inhibitors.

Authors: Jason J Reddick; Jianming Cheng; William R Roush
Journal: Org Lett Date: 2003-05-29 Impact factor: 6.005

9. The effect of the linker on the hydrolysis rate of drug-linked ester bonds.

Authors: Ronald G Schoenmakers; Petra van de Wetering; Donald L Elbert; Jeffrey A Hubbell
Journal: J Control Release Date: 2004-03-05 Impact factor: 9.776

9 in total

6 in total

1. Determining Michael Acceptor Reactivity from Kinetic, Mechanistic, and Computational Analysis for the Base-catalyzed Thiol-Michael Reaction.

Authors: Sijia Huang; Kangmin Kim; Grant M Musgrave; Marcus Sharp; Jasmine Sinha; Jeffrey W Stansbury; Charles B Musgrave; Christopher N Bowman
Journal: Polym Chem Date: 2021-05-29 Impact factor: 5.364

Multifunctional monomers based on vinyl sulfonates and vinyl sulfonamides for crosslinking thiol-Michael polymerizations: monomer reactivity and mechanical behavior.

1. Vinyl sulfone: a versatile function for simple bioconjugation and immobilization.

Review 2. Developments and recent advancements in the field of endogenous amino acid selective bond forming reactions for bioconjugation.

3. Ester-free Thiol-X Resins: New Materials with Enhanced Mechanical Behavior and Solvent Resistance.

4. Azidopropylvinylsulfonamide as a New Bifunctional Click Reagent for Bioorthogonal Conjugations: Application for DNA-Protein Cross-Linking.

5. Synthesis and anti-HIV-1 activity of a novel series of 1,4,2-benzodithiazine-dioxides.

6. Synthesis of functionalized sulfonamides via 1,3-dipolar cycloaddition of pentafluorophenyl vinylsulfonate.

7. Development of glassy step-growth thiol-vinyl sulfone polymer networks.

8. Relative rates of Michael reactions of 2'-(phenethyl)thiol with vinyl sulfones, vinyl sulfonate esters, and vinyl sulfonamides relevant to vinyl sulfonyl cysteine protease inhibitors.

9. The effect of the linker on the hydrolysis rate of drug-linked ester bonds.

1. Determining Michael Acceptor Reactivity from Kinetic, Mechanistic, and Computational Analysis for the Base-catalyzed Thiol-Michael Reaction.

2. Hydrolytically Stable Maleimide-End-Functionalized Polymers for Site-Specific Protein Conjugation.

3. On-Resin Macrocyclization of Peptides Using Vinyl Sulfonamides as a Thiol-Michael "Click" Acceptor.

4. Vinyl sulfonamide based thermosetting composites via thiol-Michael polymerization.

5. Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides.

6. In Situ Cyclization of Proteins (INCYPRO): Cross-Link Derivatization Modulates Protein Stability.