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Stereo- and regioselective azide/alkyne cycloadditions in carbonic anhydrase II via tethering, monitored by crystallography and mass spectrometry.

Wischeler JS, Sun D, Sandner NU, Linne U, Heine A, Koert U, Klebe G
Chemistry 17 5842-51 (2011)
Cited: 6 times
EuropePMC logo PMID: 21506176

Abstract

The carbonic anhydrase II mutant His64Cys was prepared and applied to tethered alkyne/azide cycloaddition reactions. The azide component could be tethered to the enzyme surface through a disulfide bridge, while the alkyne component was reversibly coordinated through a sulfonamide anchor to the zinc ion in the original catalytic center of the enzyme. The incipient orientation of the reactants in the binding site and of the formed triazole product were characterized by crystallography. The reaction progression could be monitored by HPLC-MS analysis.

Reviews citing this publication (2)

  1. New insights into the kinetic target-guided synthesis of protein ligands. Oueis E, Sabot C, Renard PY. Chem Commun (Camb) 51 12158-12169 (2015)
  2. Thermodynamic, kinetic, and structural parameterization of human carbonic anhydrase interactions toward enhanced inhibitor design. Linkuvienė V, Zubrienė A, Manakova E, Petrauskas V, Baranauskienė L, Zakšauskas A, Smirnov A, Gražulis S, Ladbury JE, Matulis D. Q Rev Biophys 51 e10 (2018)

Articles citing this publication (4)

  1. Probing the binding site of abl tyrosine kinase using in situ click chemistry. Peruzzotti C, Borrelli S, Ventura M, Pantano R, Fumagalli G, Christodoulou MS, Monticelli D, Luzzani M, Fallacara AL, Tintori C, Botta M, Passarella D. ACS Med Chem Lett 4 274-277 (2013)
  2. Synthesis and evaluation of antimalarial properties of novel 4-aminoquinoline hybrid compounds. Fisher GM, Tanpure RP, Douchez A, Andrews KT, Poulsen SA. Chem Biol Drug Des 84 462-472 (2014)
  3. Proteins analysed as virtual knots. Alexander K, Taylor AJ, Dennis MR. Sci Rep 7 42300 (2017)
  4. Guest covalent capture by a host: a biomimetic strategy for the selective functionalization of a cavity. Menard N, Reinaud O, Colasson B. Chemistry 19 642-653 (2013)


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