title: Regiospecific benzylation of tryptophan and derivatives catalyzed by a fungal dimethylallyl transferase.
abstract: A big challenge in organic synthesis is to reach a high regioselectivity. Enzymes catalyze usually highly regiospecific reactions and can function as ideal biocatalysts for such purposes. Some secondary metabolite enzymes can even use distinctly different unnatural substrates and expand therefore their potential usage in chemoenzymatic synthesis. We report here the acceptance of benzyl diphosphate as an alkyl donor by the fungal dimethylallyl transferase FgaPT2 and the regiospecific enzymatic benzylation of tryptophan and several analogues.
authors.affiliation: Institut für Pharmazeutische Biologie und Biotechnologie, Philipps Universität Marburg Deutschhausstrasse 17a, 35037 Marburg, Germany.
authors.forename: Mike
authors.initials: M
authors.lastname: Liebhold
authors.forename: Shu-Ming
authors.initials: SM
authors.lastname: Li
mesh_terms: D001232:Aspergillus fumigatus / Q000737:chemistry* / Q000201:enzymology; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D004122:Dimethylallyltranstransferase / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D015394:Molecular Structure; D014364:Tryptophan / Q000737:chemistry* / Q000378:metabolism
chemical_list: D001593:Benzyl Compounds; D014364:Tryptophan; D004122:Dimethylallyltranstransferase