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Chirality at Nitrogen, Phosphorus, and Sulfur

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Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
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Prochirality

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Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy

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Published on: September 17, 2017

Chiral PNAs with constrained open-chain backbones.

Roberto Corradini¹, Tullia Tedeschi, Stefano Sforza

¹Department of Chemistry, University of Parma, Parma, Italy.

Methods in Molecular Biology (Clifton, N.J.)

|December 4, 2013

Summary

Chiral open-chain peptide nucleic acids (PNAs) offer enhanced DNA binding and cellular uptake. This study details synthesis methods for chiral PNA monomers and optical purity assessment for improved PNA drug development.

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Combining X-Ray Crystallography with Small Angle X-Ray Scattering to Model Unstructured Regions of Nsa1 from S. Cerevisiae

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Published on: January 10, 2018

Area of Science:

Medicinal Chemistry
Organic Synthesis
Biochemistry

Background:

Chiral open-chain peptide nucleic acids (PNAs) exhibit superior helical handedness control, DNA affinity, sequence selectivity, and cellular uptake compared to achiral counterparts.
PNA synthesis can employ preformed chiral monomers or submonomeric strategies, with method selection dependent on the stereogenic center's position (C-2 or C-5).

Purpose of the Study:

To describe protocols for synthesizing PNA oligomers with chiral modifications at the C-2 and/or C-5 positions.
To present a gas chromatography (GC) method for verifying the optical purity of C-2-modified PNAs.

Main Methods:

Synthesis of PNA oligomers utilizing either preformed chiral monomers or a submonomeric approach.
Application of a submonomeric strategy to minimize racemization during solid-phase synthesis, particularly for C-2 substituted PNAs.
Development and implementation of a GC method for assessing the optical purity of C-2-modified PNA monomers and oligomers.

Main Results:

Established protocols for the synthesis of PNA oligomers incorporating C-2- and/or C-5-modified chiral monomers.
Demonstrated the effectiveness of the submonomeric approach in preserving stereochemical integrity at the C-2 position during PNA synthesis.
Validated a GC method for accurate determination of optical purity in C-2-modified PNAs.

Conclusions:

Chiral open-chain PNAs can be efficiently synthesized using tailored strategies based on the modification site.
The developed GC method provides a reliable means to ensure the stereochemical quality of C-2-modified PNAs, crucial for their biological applications.
These advancements facilitate the development of PNA-based therapeutics with improved pharmacological profiles.