Chemo-Enzymatic Generation of Highly Fluorescent Nucleoside Analogs Using Purine-Nucleoside Phosphorylase
Abstract
:1. Introduction: Fluorescent Nucleoside Analogs—An Outlook
2. Purine Nucleoside Phosphorylase as a Synthetic Tool
3. Chemo-Enzymatic Synthesis of Fluorescent Ribosides of Purines and 8-Azapurines
3.1. 8-Azaadenosine, 8-Azainosine, 8-Azaxanthosine and Derivatives
3.2. 8-Azaguanosine and Analogs
3.3. Other 8-Azapurine Analogs and Their Enzymatic Ribosylation
3.4. 8-Aza-7-Deazapurine and 8-Aza-9-Deazapurine Ribosides
3.5. Other Bicyclic Heteroaromatics
4. Chemo-Enzymatic Synthesis and Properties of The Tricyclic Purine Analogs and Their Ribosides
4.1. Adenosine Analogs
4.2. Guanosine Analogs
4.3. 2-Aminopurine Riboside and Isoguanosine Analogs
4.4. Tricyclic Azapurine Analogs
Compound | Excitation: λmax [nm] | Emission: λmax [nm] | Quantum Yield | Decay Time [ns] |
---|---|---|---|---|
1,N6-etheno-adenosine | 305 | 410 | 0.56 | 21 |
1,N6-etheno-6-β-D-ribosyl-adenine | 310 | 380 | 0.10 | nd |
1,N2-ethenoguanosine (anion) | 400 | <0.01 | nd | |
N2,3-ethenoguanosine | 261 | 400 | 0.02 | nd |
N2,3-etheno-O6-methylguanosine | 272 | 405 | 0.11 | nd |
1,N2-etheno-2-aminopurine | 248 | 473 | 0.18 | 6.9;10.3 |
1,N2-etheno-2-aminopurine-9-β-D- riboside | 295 | 463 | 0.14 | nd |
1,N2-etheno-2-aminopurine-2-β-D- riboside | 338 | ~405 | ~0.7 | nd |
N2,3-etheno-2-aminopurine | 315 | 406 | 0.73 | 3.8;8.5 |
N2,3-etheno-2-aminopurine-2-β-D- riboside | 315 | 357 | 0.29 | 2.15 |
1, N6-etheno-2-hydroxy-adenine | 295 | 415 | 0.17 | nd |
1, N6-etheno-2-hydroxy-adenosine | 295 | 415 | 0.34 | 6.1 |
1,N6-etheno-2-hydroxy-adenine-7-β-D- riboside | 294 | 360 | 0.036 | 0.8;5.2 |
1,N6-etheno-2-hydroxy-adenine-6-β-D- riboside | 303 | 425 | 0.66 | nd |
5. Conclusions and Perspectives
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Appendix A
References
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Compound | Excitation: λmax [nm] | Emission: λmax [nm] | ϕ | τ [ns] |
---|---|---|---|---|
2-aminopurine riboside | 305 | 380 | 0.68 | ~8 |
8-azaxanthosine * | 290 | 440 | >0.1 | nd |
8-azaguanosine (neutral) | 260 | 347 | <0.01 | |
8-azaguanosine (anionic, pH 10) | 278 | 362 | 0.55 | 5.6 |
8-azaguanine-N7-β-D-riboside | 290 | 420 | 0.03 | nd |
8-azaadenosine | 278 | 352 | 0.068 | 0.8 |
8-azainosine (anionic, pH 10) | 275 | 357 | 0.018 | nd |
2,6-diamino-8-azapurine- N9-β-D-riboside | 285 | 365 | 0.9 | ~6 |
2,6-diamino-8-azapurine- N7-β-D-riboside | 314 | 420 | 0.063 | 1.5;0.45 |
2,6-diamino-8-azapurine- N8-β-D-riboside | 313 | 430 | 0.41 | 10.5 |
8-aza-7-deaza-isoguanine | 288 | 370 | nd | nd |
8-aza-isoguanosine (anionic, pH 11) | 285 | 370 | ~0.1 | nd |
8-aza-7-deaza-isoguanosine * | 285 | ~430 | nd | nd |
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Stachelska-Wierzchowska, A.; Wierzchowski, J. Chemo-Enzymatic Generation of Highly Fluorescent Nucleoside Analogs Using Purine-Nucleoside Phosphorylase. Biomolecules 2024, 14, 701. https://doi.org/10.3390/biom14060701
Stachelska-Wierzchowska A, Wierzchowski J. Chemo-Enzymatic Generation of Highly Fluorescent Nucleoside Analogs Using Purine-Nucleoside Phosphorylase. Biomolecules. 2024; 14(6):701. https://doi.org/10.3390/biom14060701
Chicago/Turabian StyleStachelska-Wierzchowska, Alicja, and Jacek Wierzchowski. 2024. "Chemo-Enzymatic Generation of Highly Fluorescent Nucleoside Analogs Using Purine-Nucleoside Phosphorylase" Biomolecules 14, no. 6: 701. https://doi.org/10.3390/biom14060701