Palladium-Mediated Approach to Coumarin-Functionalized Amino Acids

Organic Letters
Lindon W K MoodieChristian Hedberg

Abstract

Incorporation of the fluorogenic l-(7-hydroxycoumarin-4-yl)ethylglycine into proteins is a valuable biological tool. Coumarins are typically accessed via the Pechmann reaction, which requires acidic conditions and lacks substrate flexibility. A Pd-mediated coupling is described between o-methoxyboronic acids and a glutamic acid derived (Z)-vinyl triflate, forming latent coumarins. Global deprotection with BBr3 forms the coumarin scaffold in a single step. This mild and scalable route yielded five analogues, including a probe suitable for use at lower pH.

References

Jan 5, 1999·Bioorganic & Medicinal Chemistry Letters·W C SunR P Haugland
Apr 21, 2001·Science·L WangP G Schultz
Aug 16, 2003·Science·Jason W ChinPeter G Schultz
Jun 29, 2004·Angewandte Chemie·Marie-Priscille BrunChristiane Garbay
Jul 6, 2006·Journal of the American Chemical Society·Jiangyun WangPeter G Schultz
Jun 11, 2008·Organic Letters·David BabinskiDoug E Frantz
Mar 9, 2010·Chemical Reviews·Renatus W SinkeldamYitzhak Tor
Mar 10, 2010·ACS Chemical Biology·Kimberly R MendesEvan R Kantrowitz
Aug 13, 2010·Beilstein Journal of Organic Chemistry·Manfred Braun, Torsten Dittrich
Dec 18, 2010·Journal of the American Chemical Society·Isaac N UgwumbaColin J Jackson
Jun 18, 2011·Chembiochem : a European Journal of Chemical Biology·Godefroid CharbonEli Chapman
Aug 9, 2011·Journal of the American Chemical Society·Sebastian Greiss, Jason W Chin
Aug 30, 2011·Journal of the American Chemical Society·Ishu SaraogiShu-ou Shan
Feb 13, 2013·Beilstein Journal of Organic Chemistry·Xinyi XuJiangyun Wang
Apr 24, 2013·Chembiochem : a European Journal of Chemical Biology·Andrew T Krueger, Barbara Imperiali
May 15, 2013·Current Opinion in Chemical Biology·Chan Hyuk KimPeter G Schultz
Aug 15, 2013·Journal of the American Chemical Society·Shengxi ChenSidney M Hecht
Feb 22, 2014·Annual Review of Biochemistry·Jason W Chin
Mar 25, 2014·Chemical Reviews·Kathrin Lang, Jason W Chin
Mar 31, 2015·Journal of the American Chemical Society·Mariana AmaroJiří Damborský
Feb 4, 2016·Organic & Biomolecular Chemistry·J M Cottam JonesA D Abell
Oct 8, 2016·Organic & Biomolecular Chemistry·Alexander H Harkiss, Andrew Sutherland

❮ Previous
Next ❯

Citations

Aug 1, 2018·Chemistry, an Asian Journal·Yogesh G ShelkeAnant R Kapdi

❮ Previous
Next ❯

Related Concepts

Related Feeds

Antibodies: Agglutination

Antibody-mediated agglutination is the clumping of cells in the presence of antibody, which binds multiple cells together. This enhances the clearance of pathogens. Find the latest research on antibody-mediated agglutination here.