Mirror‐Image Oligonucleotides: History and Emerging Applications
Open accessAbstract
As chiral molecules, naturally occurring d‐oligonucleotides have enantiomers, l‐DNA and l‐RNA, which are comprised of l‐(deoxy)ribose sugars. These mirror‐image oligonucleotides have the same physical and chemical properties as that of their native d‐counterparts, yet are highly orthogonal to the stereospecific environment of biology. Consequently, l‐oligonucleotides are resistant to nuclease degradation and many of the off‐target interactions that plague traditional d‐oligonucleotide‐based technologies; thus making them ideal for biomedical applications. Despite a flurry of interest during the early 1990s, the inability of d‐ and l‐oligonucleotides to form contiguous Watson–Crick base pairs with each other has ultimately led to the perception that l‐oligonucleotides have only limited utility. Recently, however, scientists have begun to uncover novel strategies to harness the bio‐orthogonality of l‐oligonucleotides, while overcoming (and even exploiting) their inability to Watson–Crick base pair with the natural polymer. Herein, a brief history of l‐oligonucleotide research is presented and emerging l‐oligonucleotide‐based technologies, as well as their applications in research and therapy, are presented.
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l-DNA and l-RNA are completely resistant to nuclease degradation.
“l-DNA and l-RNA are completely resistant to nuclease degradation”
From Direct Comparison of <scp>d</scp>-DNA and <scp>l</scp>-DNA Strand-Displacement Reactions in Living Mammalian Cells (2021) · cites this paper as [7]
The Introduction says l-oligonucleotides resist nuclease degradation, and the Molecular Biology section reports that l-DNA ZIP-code arrays were completely resistant. The Historical Perspective describes complete resistance only for particular l-ribonucleoside cyclic phosphates against a variety of ribonucleases under tested conditions. These passages do not establish complete resistance for l-DNA and l-RNA generally. (LLM, conf=0.85)
Experimental — accuracy not yet measuredl-DNA and l-RNA are nonimmunogenic.
“and nonimmunogenic.7”
From Direct Comparison of <scp>d</scp>-DNA and <scp>l</scp>-DNA Strand-Displacement Reactions in Living Mammalian Cells (2021) · cites this paper as [7]
l-DNA and l-RNA are less susceptible to non-specific interactions with cellular macromolecules.
“less susceptible to non-specific interactions with cellular macromolecules”
From Direct Comparison of <scp>d</scp>-DNA and <scp>l</scp>-DNA Strand-Displacement Reactions in Living Mammalian Cells (2021) · cites this paper as [7]
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Self-citation
- Authors
- Young, B. E., Kundu, N., & Sczepanski, J. T.
- Affiliations
- Texas A&M University (US)
- Corresponding author
- Sczepanski, Jonathan T.
- Venue
- Chemistry – A European Journal
- Publisher
- Wiley
- Published
- 2019-04-26
- Volume
- 25
- Issue
- 34
- Pages
- 7981-7990
- ISSN
- 0947-6539 (ISSN-L)
- 1521-3765
- PMC
- PMC6615976
- OpenAlex
- W2924169513
- Semantic Scholar
- e623aa474612b52c5158a7126d70960ba7739126
- Cited by
- 93
- References
- 104
- Citations by year
- 2026: 10 · 2025: 16 · 2024: 11 · 2023: 10 · 2022: 17 · 2021: 17 · 2020: 11 · 2019: 1
- FWCI
- 1.02
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Chemistry - A European Journal (publishedVersion)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- Funders
- Cancer Prevention and Research Institute of Texas (RR150038)
- National Institute of General Medical Sciences (R35GM124974)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Advanced biosensing and bioanalysis techniques
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › RNA Interference and Gene Delivery
- Keywords
- L-DNA, chiral molecules, nuclease resistance, off-target interactions, Watson-Crick base pairing, oligonucleotide therapeutics
- MeSH terms
- Animals, Base Sequence, DNA, Humans, Nucleic Acid Conformation, Oligonucleotides, Ribose, RNA, Stereoisomerism, Biosensing Techniques, Base Pairing, Nanotechnology, Nanostructures
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
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