A new enzyme involved in the control of the stereochemistry in the decalin formation during equisetin biosynthesis

Biochemical and Biophysical Research Communications
Naoki KatoHiroyuki Osada

Abstract

Tetramic acid containing a decalin ring such as equisetin and phomasetin is one of the characteristic scaffolds found in fungal bioactive secondary metabolites. Polyketide (PKS)-nonribosomal peptide synthetase (NRPS) hybrid enzyme is responsible for the synthesis of the polyketide scaffold conjugated with an amino acid. PKS-NRPS hybrid complex programs to create structural diversity in the polyketide backbone have begun to be investigated, yet mechanism of control of the stereochemistry in a decalin formation via a Diels-Alder cycloaddition remains uncertain. Here, we demonstrate that fsa2, which showed no homology to genes encoding proteins of known function, in the fsa cluster responsible for equisetin and fusarisetin A biosynthesis in Fusarium sp. FN080326, is involved in the control of stereochemistry in decalin formation via a Diels-Alder reaction in the equisetin biosynthetic pathway.

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Citations

Feb 13, 2016·Current Opinion in Chemical Biology·Qingfei ZhengWen Liu
Apr 18, 2015·Organic Letters·Thomas B KakuleEric W Schmidt
Jun 16, 2016·The Journal of Antibiotics·Atsushi Minami, Hideaki Oikawa
Oct 5, 2016·Current Opinion in Chemical Biology·Takuya Hashimoto, Tomohisa Kuzuyama
Dec 17, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Aida DroceJens Laurids Sørensen
Apr 23, 2016·Cell Chemical Biology·Hideaki Oikawa
Apr 13, 2017·Chemical Communications : Chem Comm·Xiaojun LiShuanhu Gao
Apr 8, 2017·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Shinji KishimotoKenji Watanabe
Aug 30, 2017·Natural Product Reports·Elizabeth Skellam
Jan 22, 2019·Chemistry : a European Journal·Benjamin R LichmanHajo Kries
Sep 14, 2017·The Journal of Antibiotics·Toshihiko NogawaHiroyuki Osada
Jan 2, 2019·Fungal biology and biotechnology·Sietske GrijseelsRasmus John Normand Frandsen
Jun 21, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xiaojing LinZhizeng Gao
Apr 10, 2021·International Journal of Biological Macromolecules·Gangming Xu, Suiqun Yang
Apr 27, 2017·Chemical Reviews·Byung-Sun JeonHung-Wen Liu
Dec 15, 2016·Journal of the American Chemical Society·Li LiYi Tang
Jan 6, 2019·Journal of the American Chemical Society·Dan TanYi Tang
Jun 15, 2021·Angewandte Chemie·Keisuke FujiyamaShingo Nagano

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