One pot 'click' reactions: tandem enantioselective biocatalytic epoxide ring opening and [3+2] azide alkyne cycloaddition.
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.
Campbell-Verduyn
Lachlan S
LS
Stratingh Institute for Chemistry, University of Groningen, Groningen, the Netherlands.
Szymański
Wiktor
W
Postema
Christiaan P
CP
Dierckx
Rudi A
RA
Elsinga
Philip H
PH
Janssen
Dick B
DB
Feringa
Ben L
BL
D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D055162:Biocatalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D006867:Hydrolases / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry
D000480:Alkynes; D001386:Azides; D004852:Epoxy Compounds; D014230:Triazoles; D006867:Hydrolases; C430848:halohydrin dehalogenase