Watson‐Crick Base Pairing of N‐Methoxy‐1,3‐Oxazinane (MOANA) Nucleoside Analogues within Double‐Helical DNA
Abstract Hairpin oligodeoxynucleotides incorporating a (2R,3S)‐4‐(methoxyamino)butane‐1,2,3‐triol residue in the middle of the double‐helical stem and opposite to either one of the canonical nucleobases or an abasic 2‐(hydroxymethyl)tetrahydrofuran‐3‐ol spacer were synthesized. Under mildly acidic c...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2023-07-01
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| Series: | ChemistryOpen |
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| Online Access: | https://doi.org/10.1002/open.202300085 |
| _version_ | 1797772325900255232 |
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| author | Mark N. K. Afari Kasper Nurmi Prof. Pasi Virta Prof. Tuomas Lönnberg |
| author_facet | Mark N. K. Afari Kasper Nurmi Prof. Pasi Virta Prof. Tuomas Lönnberg |
| author_sort | Mark N. K. Afari |
| collection | DOAJ |
| description | Abstract Hairpin oligodeoxynucleotides incorporating a (2R,3S)‐4‐(methoxyamino)butane‐1,2,3‐triol residue in the middle of the double‐helical stem and opposite to either one of the canonical nucleobases or an abasic 2‐(hydroxymethyl)tetrahydrofuran‐3‐ol spacer were synthesized. Under mildly acidic conditions, aromatic aldehydes reacted reversibly with these oligonucleotides, converting the (2R,3S)‐4‐(methoxyamino)butane‐1,2,3‐triol unit into a 2‐aryl‐N‐methoxy‐1,3‐oxazinane nucleoside analogue. The equilibrium of this reaction was found to be dependent on both the aldehyde and the nucleobase opposite to the modified residue. 9‐Formyl‐9‐deazaadenine, combining a large stacking surface with an array of hydrogen bond donors and acceptors, showed the highest affinity as well as selectivity consistent with the rules of Watson‐Crick base pairing. 5‐Formyluracil or indole‐3‐carbaldehyde, lacking in either stacking or hydrogen bonding ability, were incorporated with a much lower affinity and selectivity. |
| first_indexed | 2024-03-12T21:50:27Z |
| format | Article |
| id | doaj.art-b1da5ccb4fbb4f089903aaaabe8a8da1 |
| institution | Directory Open Access Journal |
| issn | 2191-1363 |
| language | English |
| last_indexed | 2024-03-12T21:50:27Z |
| publishDate | 2023-07-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemistryOpen |
| spelling | doaj.art-b1da5ccb4fbb4f089903aaaabe8a8da12023-07-26T04:52:28ZengWiley-VCHChemistryOpen2191-13632023-07-01127n/an/a10.1002/open.202300085Watson‐Crick Base Pairing of N‐Methoxy‐1,3‐Oxazinane (MOANA) Nucleoside Analogues within Double‐Helical DNAMark N. K. Afari0Kasper Nurmi1Prof. Pasi Virta2Prof. Tuomas Lönnberg3Department of Chemistry University of Turku Henrikinkatu 2 20500 Turku FinlandDepartment of Chemistry University of Turku Henrikinkatu 2 20500 Turku FinlandDepartment of Chemistry University of Turku Henrikinkatu 2 20500 Turku FinlandDepartment of Chemistry University of Turku Henrikinkatu 2 20500 Turku FinlandAbstract Hairpin oligodeoxynucleotides incorporating a (2R,3S)‐4‐(methoxyamino)butane‐1,2,3‐triol residue in the middle of the double‐helical stem and opposite to either one of the canonical nucleobases or an abasic 2‐(hydroxymethyl)tetrahydrofuran‐3‐ol spacer were synthesized. Under mildly acidic conditions, aromatic aldehydes reacted reversibly with these oligonucleotides, converting the (2R,3S)‐4‐(methoxyamino)butane‐1,2,3‐triol unit into a 2‐aryl‐N‐methoxy‐1,3‐oxazinane nucleoside analogue. The equilibrium of this reaction was found to be dependent on both the aldehyde and the nucleobase opposite to the modified residue. 9‐Formyl‐9‐deazaadenine, combining a large stacking surface with an array of hydrogen bond donors and acceptors, showed the highest affinity as well as selectivity consistent with the rules of Watson‐Crick base pairing. 5‐Formyluracil or indole‐3‐carbaldehyde, lacking in either stacking or hydrogen bonding ability, were incorporated with a much lower affinity and selectivity.https://doi.org/10.1002/open.202300085base pairingDNA-templated ligationdynamic base fillingoligonucleotidesoxazinanes |
| spellingShingle | Mark N. K. Afari Kasper Nurmi Prof. Pasi Virta Prof. Tuomas Lönnberg Watson‐Crick Base Pairing of N‐Methoxy‐1,3‐Oxazinane (MOANA) Nucleoside Analogues within Double‐Helical DNA ChemistryOpen base pairing DNA-templated ligation dynamic base filling oligonucleotides oxazinanes |
| title | Watson‐Crick Base Pairing of N‐Methoxy‐1,3‐Oxazinane (MOANA) Nucleoside Analogues within Double‐Helical DNA |
| title_full | Watson‐Crick Base Pairing of N‐Methoxy‐1,3‐Oxazinane (MOANA) Nucleoside Analogues within Double‐Helical DNA |
| title_fullStr | Watson‐Crick Base Pairing of N‐Methoxy‐1,3‐Oxazinane (MOANA) Nucleoside Analogues within Double‐Helical DNA |
| title_full_unstemmed | Watson‐Crick Base Pairing of N‐Methoxy‐1,3‐Oxazinane (MOANA) Nucleoside Analogues within Double‐Helical DNA |
| title_short | Watson‐Crick Base Pairing of N‐Methoxy‐1,3‐Oxazinane (MOANA) Nucleoside Analogues within Double‐Helical DNA |
| title_sort | watson crick base pairing of n methoxy 1 3 oxazinane moana nucleoside analogues within double helical dna |
| topic | base pairing DNA-templated ligation dynamic base filling oligonucleotides oxazinanes |
| url | https://doi.org/10.1002/open.202300085 |
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