Crystal Structure and Conformational Dynamics of N─N Bond‐Forming Piperazate Synthase

l ‐Piperazic acid ( l ‐Piz) is a noncanonical, α ‐hydrazino acid characterized by a 1,2‐diazinane heterocycle containing an N─N bond. It occurs in numerous natural products with potent biological activities and represents a key pharmaceutical building block. In nature, l ‐Piz is biosynthesized from l ‐ornithine via the intermediate N 5 ‐hydroxy‐ l ‐ornithine in a two‐enzyme cascade comprising a flavin adenine dinucleotide (FAD)‐dependent N ‐hydroxylating monooxygenase (NMO) and a heme‐dependent piperazate synthase (PZS). The NMO selectively hydroxylates the δ ‐amino group of l ‐ornithine, while PZS catalyzes intramolecular N─N bond formation to generate the six‐membered cyclic hydrazine scaffold of l ‐Piz. Here, we report the crystal structure, Piz‐forming activity, and molecular dynamics (MD) analysis of SbPZS, a representative PZS from Streptomyces sp. B93. High‐resolution structural analysis enabled a detailed comparison with previously characterized PZS homologs. To further delineate the molecular basis of catalysis, we performed MD simulations in combination with sequence‐based bioinformatic analyses. These studies provide insight into protein–substrate interactions, conformational dynamics, and the residues that contribute to active‐site organization. Moreover, we identify candidate hotspots for engineering to modulate substrate scope and catalytic efficiency. Collectively, our results establish a structural framework for understanding enzymatic N─N bond formation in Piz biosynthesis and lay the groundwork for future biocatalytic applications of PZSs.

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Publication Details

Journal
ChemBioChem
Published
2026-06-17
DOI
https://doi.org/10.1002/cbic.70430
Primary Topic
Enzyme Structure and Function
Type
article
Field-Weighted Citation Impact
0.00

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article

Crystal Structure and Conformational Dynamics of N─N Bond‐Forming Piperazate Synthase

Karl Gruber, Sandy Schmidt, Christian Gruber, Bastian Daniel et al.
ChemBioChem
Enzyme Structure and Function
article

Crystal Structure and Conformational Dynamics of N─N Bond‐Forming Piperazate Synthase

Karl Gruber, Sandy Schmidt, Christian Gruber, Bastian Daniel, Martin A. Hayes, Simon Schröder, Amit Singh, Nikita Pal
article en

Abstract

l ‐Piperazic acid ( l ‐Piz) is a noncanonical, α ‐hydrazino acid characterized by a 1,2‐diazinane heterocycle containing an N─N bond. It occurs in numerous natural products with potent biological activities and represents a key pharmaceutical building block. In nature, l ‐Piz is biosynthesized from l ‐ornithine via the intermediate N 5 ‐hydroxy‐ l ‐ornithine in a two‐enzyme cascade comprising a flavin adenine dinucleotide (FAD)‐dependent N ‐hydroxylating monooxygenase (NMO) and a heme‐dependent piperazate synthase (PZS). The NMO selectively hydroxylates the δ ‐amino group of l ‐ornithine, while PZS catalyzes intramolecular N─N bond formation to generate the six‐membered cyclic hydrazine scaffold of l ‐Piz. Here, we report the crystal structure, Piz‐forming activity, and molecular dynamics (MD) analysis of SbPZS, a representative PZS from Streptomyces sp. B93. High‐resolution structural analysis enabled a detailed comparison with previously characterized PZS homologs. To further delineate the molecular basis of catalysis, we performed MD simulations in combination with sequence‐based bioinformatic analyses. These studies provide insight into protein–substrate interactions, conformational dynamics, and the residues that contribute to active‐site organization. Moreover, we identify candidate hotspots for engineering to modulate substrate scope and catalytic efficiency. Collectively, our results establish a structural framework for understanding enzymatic N─N bond formation in Piz biosynthesis and lay the groundwork for future biocatalytic applications of PZSs.

ChemBioChemVol. 27(12)
University of Graz (AT), The University of Queensland (AU), University of Groningen (NL), BioTechMed-Graz (AT), AstraZeneca (Sweden) (SE), FACC (Austria) (AT)
European Commission
Openalex Percentile: Top 15%
Enzyme Structure and Function
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