One pot 'click' reactions: tandem enantioselective biocatalytic epoxide ring opening and [3+2] azide alkyne cycloaddition. 2010

Lachlan S Campbell-Verduyn, and Wiktor Szymański, and Christiaan P Postema, and Rudi A Dierckx, and Philip H Elsinga, and Dick B Janssen, and Ben L Feringa
Stratingh Institute for Chemistry, University of Groningen, Groningen, the Netherlands.

Halohydrin dehalogenase (HheC) can perform enantioselective azidolysis of aromatic epoxides to 1,2-azido alcohols which are subsequently ligated to alkynes producing chiral hydroxy triazoles in a one-pot procedure with excellent enantiomeric excess.

UI MeSH Term Description Entries
D004852 Epoxy Compounds Organic compounds that include a cyclic ether with three ring atoms in their structure. They are commonly used as precursors for POLYMERS such as EPOXY RESINS. Epoxide,Epoxides,Epoxy Compound,Oxiranes,Compound, Epoxy,Compounds, Epoxy
D006867 Hydrolases Any member of the class of enzymes that catalyze the cleavage of the substrate and the addition of water to the resulting molecules, e.g., ESTERASES, glycosidases (GLYCOSIDE HYDROLASES), lipases, NUCLEOTIDASES, peptidases (PEPTIDE HYDROLASES), and phosphatases (PHOSPHORIC MONOESTER HYDROLASES). EC 3. Hydrolase
D000480 Alkynes Hydrocarbons with at least one triple bond in the linear portion, of the general formula Cn-H2n-2. Acetylenic Compounds,Alkyne,Acetylenes
D001386 Azides Organic or inorganic compounds that contain the -N3 group. Azide
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D014230 Triazoles Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3. Triazole
D055162 Biocatalysis The facilitation of biochemical reactions with the aid of naturally occurring catalysts such as ENZYMES.

Related Publications

Lachlan S Campbell-Verduyn, and Wiktor Szymański, and Christiaan P Postema, and Rudi A Dierckx, and Philip H Elsinga, and Dick B Janssen, and Ben L Feringa
May 2018, ChemCatChem,
Lachlan S Campbell-Verduyn, and Wiktor Szymański, and Christiaan P Postema, and Rudi A Dierckx, and Philip H Elsinga, and Dick B Janssen, and Ben L Feringa
April 2011, The Journal of organic chemistry,
Lachlan S Campbell-Verduyn, and Wiktor Szymański, and Christiaan P Postema, and Rudi A Dierckx, and Philip H Elsinga, and Dick B Janssen, and Ben L Feringa
February 2022, Organic letters,
Lachlan S Campbell-Verduyn, and Wiktor Szymański, and Christiaan P Postema, and Rudi A Dierckx, and Philip H Elsinga, and Dick B Janssen, and Ben L Feringa
May 2020, Organic & biomolecular chemistry,
Lachlan S Campbell-Verduyn, and Wiktor Szymański, and Christiaan P Postema, and Rudi A Dierckx, and Philip H Elsinga, and Dick B Janssen, and Ben L Feringa
January 2014, Beilstein journal of organic chemistry,
Lachlan S Campbell-Verduyn, and Wiktor Szymański, and Christiaan P Postema, and Rudi A Dierckx, and Philip H Elsinga, and Dick B Janssen, and Ben L Feringa
December 2023, The journal of physical chemistry. A,
Lachlan S Campbell-Verduyn, and Wiktor Szymański, and Christiaan P Postema, and Rudi A Dierckx, and Philip H Elsinga, and Dick B Janssen, and Ben L Feringa
April 2011, The Journal of organic chemistry,
Lachlan S Campbell-Verduyn, and Wiktor Szymański, and Christiaan P Postema, and Rudi A Dierckx, and Philip H Elsinga, and Dick B Janssen, and Ben L Feringa
September 2010, Dalton transactions (Cambridge, England : 2003),
Lachlan S Campbell-Verduyn, and Wiktor Szymański, and Christiaan P Postema, and Rudi A Dierckx, and Philip H Elsinga, and Dick B Janssen, and Ben L Feringa
January 2015, Chemistry (Weinheim an der Bergstrasse, Germany),
Lachlan S Campbell-Verduyn, and Wiktor Szymański, and Christiaan P Postema, and Rudi A Dierckx, and Philip H Elsinga, and Dick B Janssen, and Ben L Feringa
May 2015, Scientific reports,
Copied contents to your clipboard!