The crystal and molecular structure of (R)-sirtinol – C26H22N2O2 – a chemo-sensitive enhancer and ligand in metal complexes with important bio-inorganic applications
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Ivan Bernal
,
Roger A. Lalancette
,
Ahmad Hudaihed
and
Pavel Kucheryavy
Abstract
Sirtinol is a known inhibitor of sirtuin proteins – a family of deacetylases involved in the physiology of aging. Its crystalline structure has never been determined except when bound to Fe(III) where it participates in the seven-fold coordination of the metal or to Cu(II) where it acts as a bidentate or tridentate ligand. Herein, we describe the structure of this important molecule, as follows: (a) the prevalent form of the keto-enol tautomerism in the solid state, and (b) in solution. Do they match? If not, how? The crystals of (R)-sirtinol are characterized by a large number of π–π bonded interactions linking molecules in infinite ribbons, which, in turn, are linked by additional π–π interactions of a variety of types, and by hydrogen bonds. In the latter case, we confirm by NMR that the X-ray determined position of an important H atom is on a N atom rather than on an O, which is how the molecule is usually depicted.
Funding source: No funding for this research
Funding source: There was no funding for this research.
Award Identifier / Grant number: N/A
Acknowledgments
We thank R. Gautam and E. Tomat for the generous sample of (R)-sirtinol that they sent to us for analysis.
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Research ethics: All ethical guidelines have been adhered.
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Author contributions: IB and RAL wrote much of the manuscript; PK ran the nmr experiments and wrote that part of the paper; AH crystallized the material and contributed to the structural data, along with RAL. “The authors have accepted responsibility for the entire content of this manuscript and approved its submission.”
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Competing interests: The authors state no conflict of interest.
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Research funding: The X-ray diffractometer used in these studies was purchased with support from the NSF and Rutgers University, grant 2018753.
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Data availability: The raw data can be obtained on request from the corresponding author.
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Supplementary Material
This article contains supplementary material (https://doi.org/10.1515/zkri-2024-0073).
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Articles in the same Issue
- Frontmatter
- In this issue
- Inorganic Crystal Structures (Original Paper)
- Synthesis, characterization and structure-property relations in mullite-type Pb2(Pb1−xSn x )O4 solid solution
- Temperature-dependent diffraction studies on the stannides Sr3Rh4Sn4, Sr3Ir4Sn4 and Sr2.43Eu0.57Ir4Sn4
- Organic and Metalorganic Crystal Structures (Original Paper)
- The crystal and molecular structure of (R)-sirtinol – C26H22N2O2 – a chemo-sensitive enhancer and ligand in metal complexes with important bio-inorganic applications
- Synthesis and structural characterization of supramolecular cocrystals of [(4-cyano-1-methylpyridinium)2-(18-crown-6)] diiodide
- 1-Nitronaphthalene, a non-OD, non-MDO polytype
- Synthesis and crystal structure of a tripeptide comprising a centrally placed non-coded aromatic γ-amino acid
