Chiral Peptide Nucleic Acids with a Substituent in the N-(2-Aminoethy)glycine Backbone
Abstract
:1. Introduction
2. α-PNA
2.1. Synthesis and Properties of α-PNAs
PNA a | Tm (°C) | Tm (°C) |
---|---|---|
perfect match | single mismatch | |
5'-AGTGATCTAC-3' | 5'-AGTGGTCTAC-3' | |
H-GTAGATCACT-NH2 | 50 | 40 |
H-GTAGATCACT-NH2 | 43 | - |
Sequence | Tm (°C) | Tm | |
---|---|---|---|
H-GCATGTTTGA-LLys-NH2 | 43 | ||
H-GCATGLTTTGA-LLys-NH2 | 39 | −4 | |
H-GCATGDTTTGA-LLys-NH2 | 41 | −2 | |
H-GCADTGDTTDTGA-LLys-NH2 | 47 | +4 | |
H-GDCADTGDTTDTGDA-LLys-NH2 | 50 | +7 |
2.2. Double-Duplex Invasion
2.3. Cellular Uptake of α-PNAs
3. γ-PNA
3.1. Synthesis and Properties of γ-PNAs
Backbone Modification | Tm (°C) | PNA sequence | Reference |
---|---|---|---|
Gly | 47 | a | [70] |
L-Ala | 51 | a | |
L-Val | 51 | a | |
L-Ile | 51 | a | |
L-Phe | 51 | a | |
Gly | 44 | a | [68] |
L-Ser | 48 | a | |
Gly | 49.7 | b | [62] |
L-Lys | 51.4 | b | |
D-Lys | 36.4 | b | |
Gly | 50 | c | [52] |
L-Lys | 56 | c | |
D-Lys | 32 | C |
3.2. Duplex Invasion of γ-PNAs
PNA sequences | Tm (°C) | Duplex invasion | Reference |
---|---|---|---|
PNA1: H-LLys-GACCACAGAT-LLys-NH2 | 59 | - | [75] |
PNA2: H-LLys-GACCACAGAT-LLys-NH2 | ~90 | - | |
PNA3: H-LLys-GACCACAGAT-LLys(Acr)-LLys-NH2 | ~90 | + | |
PNA4: H-LLys-GAXCACAGAT-LLys-NH2 | n.d. | + | [76,77] |
PNA5: H-LLys-GAXCAXAGAT-LLys-NH2 | n.d. | + | |
PNA6: H-LLys-GAXXAXAGAT-LLys-NH2 | n.d. | + | |
PNA7: H-LLys-GACCACAGATCTAAG-LLys-NH2 | >95 | + | [78] |
PNA8: H-LLys-TATGAGACCACAGATCTAAG-LLys-NH2 | >95 | + |
3.3. Cell Internalization of γ-PNAs and Related Modified PNAs
4. β-PNA
PNA sequence | Tm (°C) |
---|---|
H-GTAGATCACT-LLys-NH2 | 51.4 |
H-G TSAGATSCACTS-LLys-NH2 | 51.0 |
H-G TRAGATRCACTR-DLys-NH2 | n.d. |
5. Conclusions
Acknowledgments
- Sample Availability: Not available.
References
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Sugiyama, T.; Kittaka, A. Chiral Peptide Nucleic Acids with a Substituent in the N-(2-Aminoethy)glycine Backbone. Molecules 2013, 18, 287-310. https://doi.org/10.3390/molecules18010287
Sugiyama T, Kittaka A. Chiral Peptide Nucleic Acids with a Substituent in the N-(2-Aminoethy)glycine Backbone. Molecules. 2013; 18(1):287-310. https://doi.org/10.3390/molecules18010287
Chicago/Turabian StyleSugiyama, Toru, and Atsushi Kittaka. 2013. "Chiral Peptide Nucleic Acids with a Substituent in the N-(2-Aminoethy)glycine Backbone" Molecules 18, no. 1: 287-310. https://doi.org/10.3390/molecules18010287