title: Assessing oxazole bioisosteres as mutasynthons on the rhizoxin assembly line.
abstract: Chain armor against tumor cells: The oxazole side chain in the antimitotic agent rhizoxin S2 (1) was successfully replaced through mutasynthesis by using an engineered mutant impaired in heterocyclization. Incorporation of 12 non-natural surrogates into fully processed rhizoxin analogues revealed a remarkable substrate flexibility of the PKS-NRPS hybrid.
authors.affiliation: Department of Biomolecular Chemistry, Hans Knöll Institute, Leibniz Institute for Natural Product Research and Infection Biology, Beutenbergstrasse 11a, 07745 Jena, Germany.
authors.forename: Björn
authors.initials: B
authors.lastname: Kusebauch
authors.forename: Nicole
authors.initials: N
authors.lastname: Brendel
authors.forename: Heike
authors.initials: H
authors.lastname: Kirchner
authors.forename: Hans-Martin
authors.initials: HM
authors.lastname: Dahse
authors.forename: Christian
authors.initials: C
authors.lastname: Hertweck
mesh_terms: D000595:Amino Acid Sequence; D000903:Antibiotics, Antineoplastic / Q000737:chemistry / Q000378:metabolism*; D019117:Burkholderia / Q000737:chemistry / Q000201:enzymology* / Q000235:genetics* / Q000378:metabolism; D005800:Genes, Fungal; D056426:Genetic Loci; D018942:Macrolides / Q000737:chemistry / Q000378:metabolism*; D008969:Molecular Sequence Data; D009154:Mutation; D010080:Oxazoles / Q000737:chemistry / Q000378:metabolism*; D010453:Peptide Synthases / Q000235:genetics / Q000378:metabolism; D048630:Polyketide Synthases / Q000235:genetics / Q000378:metabolism
chemical_list: D000903:Antibiotics, Antineoplastic; D018942:Macrolides; D010080:Oxazoles; D048630:Polyketide Synthases; C041443:rhizoxin; D010453:Peptide Synthases