Enzymatic Formation of Indolactam Scaffold by C−N Bond‐Forming Cytochrome P450 Oxidases in Teleocidin Biosynthesis

This report details the discovery and characterization of a versatile bacterial cytochrome P450, NzeB, which catalyzes the dimerization of diketopiperazines via enzymatic C–H functionalization. This includes the first high-resolution crystal structure of a diketopiperazine dimerase, which along with active site via mutagenesis and quantum mechanical calculations, provides insight into the selectivity and mechanism of these enzymes.

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Structure and Function of NzeB, a Versatile C–C and C–N Bond Forming Diketopiperazine Dimerase

10.26434/chemrxiv.12307439.v1 ◽

2020 ◽

Author(s):

Vikram V. Shende ◽

Yogan Khatri ◽

Sean A. Newmister ◽

Jacob N. Sanders ◽

Petra Lindovska ◽

...

Keyword(s):

Crystal Structure ◽

Cytochrome P450 ◽

Active Site ◽

Structure And Function ◽

Quantum Mechanical ◽

Quantum Mechanical Calculations ◽

Bond Forming ◽

And Function ◽

Insight Into

This report details the discovery and characterization of a versatile bacterial cytochrome P450, NzeB, which catalyzes the dimerization of diketopiperazines via enzymatic C–H functionalization. This includes the first high-resolution crystal structure of a diketopiperazine dimerase, which along with active site via mutagenesis and quantum mechanical calculations, provides insight into the selectivity and mechanism of these enzymes.

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Exploiting a C–N Bond Forming Cytochrome P450 Monooxygenase for C–S Bond Formation

Angewandte Chemie ◽

10.1002/ange.201916269 ◽

2020 ◽

Vol 132 (10) ◽

pp. 4017-4022 ◽

Cited By ~ 2

Author(s):

Iori Morita ◽

Takahiro Mori ◽

Takaaki Mitsuhashi ◽

Shotaro Hoshino ◽

Yoshimasa Taniguchi ◽

...

Keyword(s):

Cytochrome P450 ◽

Bond Formation ◽

Cytochrome P450 Monooxygenase ◽

P450 Monooxygenase ◽

Bond Forming

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Molecular evolution of a cytochrome P450 for the synthesis of potential antidepressant (2R,6R)-hydroxynorketamine

Chemical Communications ◽

10.1039/d0cc06729f ◽

2021 ◽

Author(s):

Ansgar Bokel ◽

Michael C. Hutter ◽

Vlada B. Urlacher

Keyword(s):

Cytochrome P450 ◽

Molecular Evolution ◽

Cytochrome P450 Monooxygenase ◽

P450 Monooxygenase ◽

Effective Synthesis

Engineered cytochrome P450 monooxygenase CYP154E1 enables the effective synthesis of the potential antidepressant (2R,6R)-hydroxynorketamine via N-demethylation and regio- and stereoselective hydroxylation of (R)-ketamine.

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