Characterization of CYP71AX36 from Sunflower (Helianthus annuus L., Asteraceae)
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Characterization of CYP71AX36 from Sunflower (Helianthus annuus L., Asteraceae). / Frey, Maximilian; Klaiber, Iris; Conrad, Jürgen; Bersch, Aylin; Pateraki, Irini; Ro, Dae Kyun; Spring, Otmar.
I: Scientific Reports, Bind 9, 14295, 2019, s. 1-8.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Characterization of CYP71AX36 from Sunflower (Helianthus annuus L., Asteraceae)
AU - Frey, Maximilian
AU - Klaiber, Iris
AU - Conrad, Jürgen
AU - Bersch, Aylin
AU - Pateraki, Irini
AU - Ro, Dae Kyun
AU - Spring, Otmar
PY - 2019
Y1 - 2019
N2 - Sesquiterpene lactones (STL) are a subclass of isoprenoids with many known bioactivities frequently found in the Asteraceae family. In recent years, remarkable progress has been made regarding the biochemistry of STL, and today the biosynthetic pathway of the core backbones of many STLs has been elucidated. Consequently, the focus has shifted to the discovery of the decorating enzymes that can modify the core skeleton with functional hydroxy groups. Using in vivo pathway reconstruction assays in heterologous organisms such as Saccharomyces cerevisiae and Nicotiana benthamiana, we have analyzed several cytochrome P450 enzyme genes of the CYP71AX subfamily from Helianthus annuus clustered in close proximity to one another on the sunflower genome. We show that one member of this subfamily, CYP71AX36, can catalyze the conversion of costunolide to 14-hydroxycostunolide. The catalytic activity of CYP71AX36 may be of use for the chemoenzymatic production of antileukemic 14-hydroxycostunolide derivatives and other STLs of pharmaceutical interest. We also describe the full 2D-NMR assignment of 14-hydroxycostunolide and provide all 13C chemical shifts of the carbon skeleton for the first time.
AB - Sesquiterpene lactones (STL) are a subclass of isoprenoids with many known bioactivities frequently found in the Asteraceae family. In recent years, remarkable progress has been made regarding the biochemistry of STL, and today the biosynthetic pathway of the core backbones of many STLs has been elucidated. Consequently, the focus has shifted to the discovery of the decorating enzymes that can modify the core skeleton with functional hydroxy groups. Using in vivo pathway reconstruction assays in heterologous organisms such as Saccharomyces cerevisiae and Nicotiana benthamiana, we have analyzed several cytochrome P450 enzyme genes of the CYP71AX subfamily from Helianthus annuus clustered in close proximity to one another on the sunflower genome. We show that one member of this subfamily, CYP71AX36, can catalyze the conversion of costunolide to 14-hydroxycostunolide. The catalytic activity of CYP71AX36 may be of use for the chemoenzymatic production of antileukemic 14-hydroxycostunolide derivatives and other STLs of pharmaceutical interest. We also describe the full 2D-NMR assignment of 14-hydroxycostunolide and provide all 13C chemical shifts of the carbon skeleton for the first time.
U2 - 10.1038/s41598-019-50520-6
DO - 10.1038/s41598-019-50520-6
M3 - Journal article
C2 - 31586110
AN - SCOPUS:85072926353
VL - 9
SP - 1
EP - 8
JO - Scientific Reports
JF - Scientific Reports
SN - 2045-2322
M1 - 14295
ER -
ID: 234212573