Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

Chemical Reviews
Vinod K TiwariXi Chen

Abstract

Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC), popularly known as the "click reaction", serves as the most potent and highly dependable tool for facile construction of simple to complex architectures at the molecular level. Click-knitted threads of two exclusively different molecular entities have created some really interesting structures for more than 15 years with a broad spectrum of applicability, including in the fascinating fields of synthetic chemistry, medicinal science, biochemistry, pharmacology, material science, and catalysis. The unique properties of the carbohydrate moiety and the advantages of highly chemo- and regioselective click chemistry, such as mild reaction conditions, efficient performance with a wide range of solvents, and compatibility with different functionalities, together produce miraculous neoglycoconjugates and neoglycopolymers with various synthetic, biological, and pharmaceutical applications. In this review we highlight the successful advancement of Cu(I)-catalyzed click chemistry in glycoscience and its applications as well as future scope in different streams of applied sciences.

References

Jan 1, 1994·Advances in Carbohydrate Chemistry and Biochemistry·R R Schmidt, W Kinzy
Nov 4, 1994·Science·P E DawsonS B Kent
Jul 5, 1994·Proceedings of the National Academy of Sciences of the United States of America·C F Liu, J P Tam
Jul 3, 1999·Trends in Pharmacological Sciences·J P VincentP Kitabgi
Feb 9, 2000·Journal of Pharmaceutical Sciences·E RedentiJ Szejtli
Mar 17, 2000·Science·E Saxon, C R Bertozzi
Aug 24, 2000·Organic Letters·F G Calvo-FloresF Santoyo-González
Mar 28, 2001·Science·C R Bertozzi, L L Kiessling
Jun 26, 2001·Glycoconjugate Journal·R T Lee, Y C Lee
Dec 26, 2001·Chemical Reviews·K H JungR R Schmidt
Dec 26, 2001·Proceedings of the National Academy of Sciences of the United States of America·Kristi L KiickCarolyn R Bertozzi
Feb 14, 2002·Chemical Reviews·Joseph J Lundquist, Eric J Toone
Feb 14, 2002·Chemical Reviews·Benjamin G Davis
Feb 19, 2002·Chemical Reviews·Sergey A. Nepogodiev, J. Fraser Stoddart
Feb 19, 2002·Chemical Reviews·Kaneto UekamaTetsumi Irie
Sep 5, 2002·Journal of the American Chemical Society·Paul T NyffelerChi-Huey Wong
Sep 28, 2002·European Journal of Medicinal Chemistry·R P TripathiB S Srivastava
Nov 28, 2002·Journal of the American Chemical Society·Fabio FazioChi-Huey Wong
Dec 10, 2002·Current Opinion in Chemical Biology·Mary J Cloninger
Dec 31, 2002·Chemistry : a European Journal·Hernán A OrgueiraPeter H Seeberger
Mar 13, 2003·Journal of the American Chemical Society·Qian WangM G Finn
Mar 28, 2003·Bioorganic & Medicinal Chemistry·V K TiwariR D Walter
Apr 17, 2003·Journal of the American Chemical Society·Anna E SpeersBenjamin F Cravatt
Apr 26, 2003·Organic Letters·Jeroen D C CodéeGijs A van der Marel
May 24, 2003·Organic Letters·Francisco Pérez-BalderasFrancisco Santoyo-González
Jun 25, 2003·Toxicology·Lisa M Gaetke, Ching Kuang Chow
Jul 5, 2003·Organic Letters·Scott T HandyGary Dickenson
Jul 19, 2003·Chemical Communications : Chem Comm·Suri IyerElliot L Chaikof
Aug 9, 2003·Journal of the American Chemical Society·Lac V LeeChi-Huey Wong
Mar 1, 1957·Biochimica Et Biophysica Acta·A GOTTSCHALK
Oct 24, 2003·Organic Letters·Sabine Arndt, Linda C Hsieh-Wilson
Nov 11, 2003·Nature Biotechnology·Xun FuJon S Thorson

❮ Previous
Next ❯

Citations

Apr 18, 2016·Carbohydrate Research·Xiao-Peng HeGuo-Rong Chen
Aug 16, 2016·Glycoconjugate Journal·Vanessa Leiria CampoMarcelo Dias-Baruffi
Sep 9, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Alessandro Mandoli
Oct 5, 2016·Glycoconjugate Journal·Pratibha DwivediVinod K Tiwari
Sep 30, 2016·The Journal of Organic Chemistry·Isravel MuthukrishnanVellaisamy Sridharan
Jan 14, 2017·The Journal of Organic Chemistry·Enrique Barragan, Alejandro Bugarin
Feb 10, 2017·Organic Letters·Asier GoitiaArkaitz Correa
Apr 19, 2017·Materials Science & Engineering. C, Materials for Biological Applications·Flavia A MartinIoan Turcu
Apr 27, 2017·Organic & Biomolecular Chemistry·Benedetta BertolottiJitka Moravcová
Jul 14, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Srinivasan Chandrasekaran, Ramesh Ramapanicker
Dec 9, 2016·Chemical Communications : Chem Comm·Karen WrightFrançois Couty
Mar 1, 2017·Physical Chemistry Chemical Physics : PCCP·Hong Yan ZouCheng Zhi Huang
Mar 14, 2017·Chemical Communications : Chem Comm·Feng LiYao Fu
Oct 7, 2016·Chemical Communications : Chem Comm·Q FuG G Qiao
Sep 16, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Neha SareenSubrato Bhattacharya
Dec 9, 2017·Journal of Biomedical Materials Research. Part B, Applied Biomaterials·Angela ScalaGiovanni Grassi
Sep 1, 2018·Journal of Enzyme Inhibition and Medicinal Chemistry·Andrea BistrovićSilvana Raić-Malić
Aug 4, 2018·Chemistry : a European Journal·Jiaxin QuanHaibing Li
Nov 1, 2018·Organic & Biomolecular Chemistry·Silvia Roscales, Joaquín Plumet
Nov 30, 2018·Chemical Communications : Chem Comm·Puja SahaJyotirmayee Dash
Apr 18, 2019·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Philippe Compain
Feb 20, 2019·Chemistry : a European Journal·Trevor A HamlinF Matthias Bickelhaupt
Dec 26, 2017·Angewandte Chemie·Xiaojun ZengBo Xu
Jun 4, 2019·Organic & Biomolecular Chemistry·Anji ChenGuijun Wang
Jul 16, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Joseph P ByrneMartin Albrecht

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.