Literature DB >> 22491759

Thiol-yne coupling: revisiting old concepts as a breakthrough for up-to-date applications.

Alessandro Massi1, Daniele Nanni.   

Abstract

Radical thiol-yne coupling (TYC) has emerged as one of the most appealing click chemistry procedures, appearing as a sound candidate for replacing/complementing other popular click reactions such as the thiol-ene coupling (TEC) and the Cu-catalysed azide-alkyne cycloaddition (CuAAC). Radical TYC is indeed a metal-free reaction suitable for biomedical applications, and its mechanistic features often make it more efficient than its TEC sister reaction and more suitable for multifaceted derivatisations in the materials chemistry and bioconjugation realms. This article reviews the fascinating results obtained in those fields in very recent years.

Entities:  

Year:  2012        PMID: 22491759     DOI: 10.1039/c2ob25217a

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  14 in total

Review 1.  Photopolymerizable Biomaterials and Light-Based 3D Printing Strategies for Biomedical Applications.

Authors:  Claire Yu; Jacob Schimelman; Pengrui Wang; Kathleen L Miller; Xuanyi Ma; Shangting You; Jiaao Guan; Bingjie Sun; Wei Zhu; Shaochen Chen
Journal:  Chem Rev       Date:  2020-04-23       Impact factor: 60.622

2.  Hydrothiolation of benzyl mercaptan to arylacetylene: application to the synthesis of (E) and (Z)-isomers of ON 01910·Na (Rigosertib®), a phase III clinical stage anti-cancer agent.

Authors:  Venkat R Pallela; Muralidhar R Mallireddigari; Stephen C Cosenza; Balaiah Akula; D R C Venkata Subbaiah; E Premkumar Reddy; M V Ramana Reddy
Journal:  Org Biomol Chem       Date:  2013-02-06       Impact factor: 3.876

3.  Facile functionalization of polyesters through thiol-yne chemistry for the design of degradable, cell-penetrating and gene delivery dual-functional agents.

Authors:  Zhonghai Zhang; Lichen Yin; Yunxiang Xu; Rong Tong; Yanbing Lu; Jie Ren; Jianjun Cheng
Journal:  Biomacromolecules       Date:  2012-10-26       Impact factor: 6.988

4.  A New Methodology for Assessing Macromolecular Click Reactions and Its Application to Amine--Tertiary Isocyanate Coupling for Polymer Ligation.

Authors:  Guillaume Gody; Derrick A Roberts; Thomas Maschmeyer; Sébastien Perrier
Journal:  J Am Chem Soc       Date:  2016-03-21       Impact factor: 15.419

5.  Synthesis of three-dimensional porous hyper-crosslinked polymers via thiol-yne reaction.

Authors:  Mathias Lang; Alexandra Schade; Stefan Bräse
Journal:  Beilstein J Org Chem       Date:  2016-11-29       Impact factor: 2.883

6.  Visible light mediated metal-free thiol-yne click reaction.

Authors:  Sergey S Zalesskiy; Nikita S Shlapakov; Valentine P Ananikov
Journal:  Chem Sci       Date:  2016-07-12       Impact factor: 9.825

7.  Fast and efficient synthesis of microporous polymer nanomembranes via light-induced click reaction.

Authors:  Qi An; Youssef Hassan; Xiaotong Yan; Peter Krolla-Sidenstein; Tawheed Mohammed; Mathias Lang; Stefan Bräse; Manuel Tsotsalas
Journal:  Beilstein J Org Chem       Date:  2017-03-17       Impact factor: 2.883

8.  Visible-Light-Mediated Selective Arylation of Cysteine in Batch and Flow.

Authors:  Cecilia Bottecchia; Maarten Rubens; Smita B Gunnoo; Volker Hessel; Annemieke Madder; Timothy Noël
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-01       Impact factor: 15.336

9.  On terminal alkynes that can react with active-site cysteine nucleophiles in proteases.

Authors:  Reggy Ekkebus; Sander I van Kasteren; Yogesh Kulathu; Arjen Scholten; Ilana Berlin; Paul P Geurink; Annemieke de Jong; Soenita Goerdayal; Jacques Neefjes; Albert J R Heck; David Komander; Huib Ovaa
Journal:  J Am Chem Soc       Date:  2013-02-15       Impact factor: 15.419

10.  Stapling of unprotected helical peptides via photo-induced intramolecular thiol-yne hydrothiolation.

Authors:  Yuan Tian; Jingxu Li; Hui Zhao; Xiangze Zeng; Dongyuan Wang; Qisong Liu; Xiaogang Niu; Xuhui Huang; Naihan Xu; Zigang Li
Journal:  Chem Sci       Date:  2016-02-05       Impact factor: 9.825

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