Expanding the Rubterolone Family: Intrinsic Reactivity and Directed Diversification of PKS-derived Pyrans
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Expanding the Rubterolone Family : Intrinsic Reactivity and Directed Diversification of PKS-derived Pyrans. / Guo, Huijuan; Benndorf, René; König, Stefanie; Leichnitz, Daniel; Weigel, Christiane; Peschel, Gundela; Berthel, Patrick; Kaiser, Marcel; Steinbeck, Christoph; Werz, Oliver; Poulsen, Michael; Beemelmanns, Christine.
In: Chemistry - A European Journal, Vol. 24, No. 44, 2018, p. 11319-11324.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Expanding the Rubterolone Family
T2 - Intrinsic Reactivity and Directed Diversification of PKS-derived Pyrans
AU - Guo, Huijuan
AU - Benndorf, René
AU - König, Stefanie
AU - Leichnitz, Daniel
AU - Weigel, Christiane
AU - Peschel, Gundela
AU - Berthel, Patrick
AU - Kaiser, Marcel
AU - Steinbeck, Christoph
AU - Werz, Oliver
AU - Poulsen, Michael
AU - Beemelmanns, Christine
PY - 2018
Y1 - 2018
N2 - We characterized two key biosynthetic intermediates of the intriguing rubterolone family (tropolone alkaloids) that contain a highly reactive pyran moiety (in equilibrium with the hydrolyzed 1,5-dione form) and undergo spontaneous pyridine formation in the presence of primary amines. We exploited the intrinsic reactivity of the pyran moiety and isolated several new rubterolone derivatives, two of which contain a unique thiazolidine moiety. Three rubterolone derivatives were chemically modified with fluorescence and biotin tags using peptide coupling and click reaction. Overall, eight derivatives were fully characterized by HRMS/MS and 1D and 2D NMR spectroscopy and their antimicrobial, cytotoxic, anti-inflammatory and antiparasitic activities evaluated.
AB - We characterized two key biosynthetic intermediates of the intriguing rubterolone family (tropolone alkaloids) that contain a highly reactive pyran moiety (in equilibrium with the hydrolyzed 1,5-dione form) and undergo spontaneous pyridine formation in the presence of primary amines. We exploited the intrinsic reactivity of the pyran moiety and isolated several new rubterolone derivatives, two of which contain a unique thiazolidine moiety. Three rubterolone derivatives were chemically modified with fluorescence and biotin tags using peptide coupling and click reaction. Overall, eight derivatives were fully characterized by HRMS/MS and 1D and 2D NMR spectroscopy and their antimicrobial, cytotoxic, anti-inflammatory and antiparasitic activities evaluated.
KW - Biosynthetic pathway
KW - Chemical probes
KW - Natural products
KW - Polyketides
KW - Tropolone alkaloids
U2 - 10.1002/chem.201802066
DO - 10.1002/chem.201802066
M3 - Journal article
C2 - 29846024
AN - SCOPUS:85050605010
VL - 24
SP - 11319
EP - 11324
JO - Chemistry: A European Journal
JF - Chemistry: A European Journal
SN - 0947-6539
IS - 44
ER -
ID: 201188776