PROCESSES OF 1,3-DIPOLAR CYCLOADDITION IN NUCLEOSIDE, NUCLEOTIDE AND BIO CONJUGATION AND ITS IMPORTANCE IN MEDICINAL CHEMISTRY
DOI:
https://doi.org/10.36320/ajb/v15.i1.11725Keywords:
Cycloaddition, Huisgen azide-alkyne reaction, biocongugationAbstract
In the 1,3-dipolar cycloaddition, a 1,3-dipole and a dipolarophile interact chemically to produce a five-membered ring. The Huisgen cycloaddition occurs when an organic azide and an alkyne unite to form a 1,3-dipolar cycloaddition that results in a 1,2,3-triazole. 1,3-dipolar cycloaddition is an essential step in the regio- and stereoselective synthesis of five-membered heterocycles and their ring-opened acyclic derivatives. Some of the cycloadducts produced by these reactions were converted into enantiopure precursors known to exist in some biologically active chemicals as well as an active stereoisomer of a pine sawfly sex pheromone. The synthesis of several new enantiopure organocatalysts that were shown to be helpful in some The synthetic utility of these 1,3-dipolar cycloaddition processes with nitrones and a,b-unsaturated aldehydes was further demonstrated. There are times when these reactions have modest to moderate diastereofacial selectivity. the choose actual and nonracemic have improved. Compound collections are created in chemical biology research using the BIOS concept, which draws its inspiration from natural product scaffolds. In BIOS, the primary criterion utilized to develop hypotheses for the design and synthesis of targeted chemical libraries is biological relevance. Because they outline the chemical domains that nature has explored, the underlying scaffolds of natural product classes in particular serve as an inspiration for BIOS because they can be thought of as "trivet can often be achieved if both the azomethine ylide and the dipolarophile are chi privileged
Downloads
References
Sykes Peter. A guidebook to Mechanism In Organic Chemistry; 6th Edition, 2018;340-357.
Morrison Robert Thornton. Boyd Robert Neilson; Organic Chemistry, 6th Edition, 2009;1022- 1066.
Loudon and Marc G. Organic Chemistry, 4th Edition. 2002;1172-1214.
Acharjee N, Banerjee A and Gayen B. Cycloaddition Approach to Five-Membered Heterocycles. Journal of Indian Chemical Society. 2017;1857-1877.
Huisgen R, Grashev R and Sauer J. Chemistry of Alkenes; Interscience. 1964;806-877.
Rostovtsev VV, Green LG, Fokin VV and Sharpless KB. Angew Chem Int. Ed; 2021;41:2596- 2599. DOI: https://doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
Amantini D, Fringuelli F, Piermatti O, Pizzo F, Zunino E and Vaccaro L. Journal Org Chem. 2005;70:6526-6529. DOI: https://doi.org/10.1021/jo0507845
Himo F, Lovell T, Hilgraf R, Rostvotsev VV, Noodleman L, Sharpless KB and Fokin VV. Journal of Americal Chemical Society. 2005;127:210-216. DOI: https://doi.org/10.1021/ja0471525
Boren BC, Narayan S, Rasmussen LK, Zhang L, Zhao H, Lin Z, Jia G and Fokin VV. Journal Americal Chemical Society. 2008;130:8923-8930. DOI: https://doi.org/10.1021/ja0749993
Martin Breugst& Hans-Ulrich Reissig . The Huisgen Reaction: Milestones of the 1,3-Dipolar Cycloaddition. journal of the German Chemical Society (GDCh). 2020 https://doi.org/10.1002/anie.202003115 DOI: https://doi.org/10.1002/anie.202003115
Hein Jason E and Fokin Valeri V. Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper (I) acetylides; Chem Soc Review. 2021;39(4):1302-1315 . DOI: https://doi.org/10.1039/b904091a
Meenakshi Choudhary, Samarjeet Siwal & Kaushik Mallick . Journal of Scientific Reports . 2020 ; 8(2) : 278–308 .
Wendy S. Jen, John J. M. Wiener, and David W. C. MacMillan . New Strategies for Organic Catalysis: The First Enantioselective Organocatalytic 1,3-Dipolar Cycloaddition . J. Am. Chem. Soc. 2000, 122, 40, 9874– 9875. DOI: https://doi.org/10.1021/ja005517p
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2023 Aseel Fadhil Kareem, Sahar FAdhil Abbas, Hayfaa A. Mubarak, Hameed
This work is licensed under a Creative Commons Attribution 4.0 International License.
which allows users to copy, create extracts, abstracts, and new works from the Article, alter and revise the Article, and make commercial use of the Article (including reuse and/or resale of the Article by commercial entities), provided the user gives appropriate credit (with a link to the formal publication through the relevant DOI), provides a link to the license, indicates if changes were made and the licensor is not represented as endorsing the use made of the work.