Perquinolines A-C: Unprecedented Bacterial Tetrahydroisoquinolines Involving an Intriguing Biosynthesis

Rebets Y, Nadmid S, Paulus C, Dahlem C, Herrmann J, Huebner H, Rückert C, Kiemer AK, Gmeiner P, Kalinowski J, Mueller R, et al. (2019)
Angewandte Chemie International Edition 58(37): 12930-12934.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Metabolic profiling of Streptomyces sp. IB2014/016-6 led to the identification of three new tetrahydroisoquinoline natural products, perquinolines A-C (1-3). Labelled precursor feeding studies and the cloning of the pqr biosynthetic gene cluster revealed that 1-3 are assembled by the action of several unusual enzymes. The biosynthesis starts with the condensation of succinyl-CoA and l-phenylalanine catalyzed by the amino-7-oxononanoate synthase-like enzyme PqrA, representing rare chemistry in natural product assembly. The second condensation and cyclization events are conducted by PqrG, an enzyme resembling an acyl-CoA ligase. Last, ATP-grasp RimK-type ligase PqrI completes the biosynthesis by transferring a gamma-aminobutyric acid or beta-alanine moiety. The discovered pathway represents a new route for assembling the tetrahydroisoquinoline cores of natural products.
Stichworte
8-amino-7-oxononanoate synthase; biosynthesis; natural product; Streptomyces; tetrahydroisoquinoline
Erscheinungsjahr
2019
Zeitschriftentitel
Angewandte Chemie International Edition
Band
58
Ausgabe
37
Seite(n)
12930-12934
ISSN
1433-7851
eISSN
1521-3773
Page URI
https://pub.uni-bielefeld.de/record/2937344

Zitieren

Rebets Y, Nadmid S, Paulus C, et al. Perquinolines A-C: Unprecedented Bacterial Tetrahydroisoquinolines Involving an Intriguing Biosynthesis. Angewandte Chemie International Edition. 2019;58(37):12930-12934.
Rebets, Y., Nadmid, S., Paulus, C., Dahlem, C., Herrmann, J., Huebner, H., Rückert, C., et al. (2019). Perquinolines A-C: Unprecedented Bacterial Tetrahydroisoquinolines Involving an Intriguing Biosynthesis. Angewandte Chemie International Edition, 58(37), 12930-12934. doi:10.1002/anie.201905538
Rebets, Y., Nadmid, S., Paulus, C., Dahlem, C., Herrmann, J., Huebner, H., Rückert, C., Kiemer, A. K., Gmeiner, P., Kalinowski, J., et al. (2019). Perquinolines A-C: Unprecedented Bacterial Tetrahydroisoquinolines Involving an Intriguing Biosynthesis. Angewandte Chemie International Edition 58, 12930-12934.
Rebets, Y., et al., 2019. Perquinolines A-C: Unprecedented Bacterial Tetrahydroisoquinolines Involving an Intriguing Biosynthesis. Angewandte Chemie International Edition, 58(37), p 12930-12934.
Y. Rebets, et al., “Perquinolines A-C: Unprecedented Bacterial Tetrahydroisoquinolines Involving an Intriguing Biosynthesis”, Angewandte Chemie International Edition, vol. 58, 2019, pp. 12930-12934.
Rebets, Y., Nadmid, S., Paulus, C., Dahlem, C., Herrmann, J., Huebner, H., Rückert, C., Kiemer, A.K., Gmeiner, P., Kalinowski, J., Mueller, R., Luzhetskyy, A.: Perquinolines A-C: Unprecedented Bacterial Tetrahydroisoquinolines Involving an Intriguing Biosynthesis. Angewandte Chemie International Edition. 58, 12930-12934 (2019).
Rebets, Yuriy, Nadmid, Suvd, Paulus, Constanze, Dahlem, Charlotte, Herrmann, Jennifer, Huebner, Harald, Rückert, Christian, Kiemer, Alexandra K., Gmeiner, Peter, Kalinowski, Jörn, Mueller, Rolf, and Luzhetskyy, Andriy. “Perquinolines A-C: Unprecedented Bacterial Tetrahydroisoquinolines Involving an Intriguing Biosynthesis”. Angewandte Chemie International Edition 58.37 (2019): 12930-12934.

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