2 '-Substituted 2-amino-3-methylpyridine ribonucleosides in triplex-forming oligonucleotides: triplex stability is determined by chemical environment
A new synthetic route to the phosphoramidite monomer of 2-amino-3-methyl-5-(2′-O-methyl-β-d-ribofuranosyl)pyridine (Me-MAP) and its 2′-O-methoxyethyl analogue (MOE-MAP) has been established using d-ribose and 2-amino-3-methyl-5-bromopyridine as precursors. Ultraviolet melting and DNase I footprintin...
| প্রধান লেখক: | , , , , , , , |
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| বিন্যাস: | Journal article |
| ভাষা: | English |
| প্রকাশিত: |
2011
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| _version_ | 1826262528437518336 |
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| author | Lou, C Xiao, Q Tailor, R Ben Gaied, N Gale, N Light, M Fox, K Brown, T |
| author_facet | Lou, C Xiao, Q Tailor, R Ben Gaied, N Gale, N Light, M Fox, K Brown, T |
| author_sort | Lou, C |
| collection | OXFORD |
| description | A new synthetic route to the phosphoramidite monomer of 2-amino-3-methyl-5-(2′-O-methyl-β-d-ribofuranosyl)pyridine (Me-MAP) and its 2′-O-methoxyethyl analogue (MOE-MAP) has been established using d-ribose and 2-amino-3-methyl-5-bromopyridine as precursors. Ultraviolet melting and DNase I footprinting studies indicate that the triplex stabilizing properties of 2′-modified MAPs are determined by the conformation of the entire oligonucleotide backbone. Me-MAP confers a higher triplex stability than 2′-deoxycytidine whereas triplex stabilization by MOE-MAP is similar to that of dC. Incorporation of Me-MAP or MOE-MAP into oligonucleotides renders them dramatically more resistant to degradation by serum nucleases than incorporation of 2-amino-3-methyl-5-(2′-deoxy-β-d-ribofuranosyl) pyridine (dMAP) or dC. © The Royal Society of Chemistry 2011. |
| first_indexed | 2024-03-06T19:37:38Z |
| format | Journal article |
| id | oxford-uuid:1f958f18-2320-44a6-aa7b-f8cd6bca34fc |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T19:37:38Z |
| publishDate | 2011 |
| record_format | dspace |
| spelling | oxford-uuid:1f958f18-2320-44a6-aa7b-f8cd6bca34fc2022-03-26T11:22:39Z2 '-Substituted 2-amino-3-methylpyridine ribonucleosides in triplex-forming oligonucleotides: triplex stability is determined by chemical environmentJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:1f958f18-2320-44a6-aa7b-f8cd6bca34fcEnglishSymplectic Elements at Oxford2011Lou, CXiao, QTailor, RBen Gaied, NGale, NLight, MFox, KBrown, TA new synthetic route to the phosphoramidite monomer of 2-amino-3-methyl-5-(2′-O-methyl-β-d-ribofuranosyl)pyridine (Me-MAP) and its 2′-O-methoxyethyl analogue (MOE-MAP) has been established using d-ribose and 2-amino-3-methyl-5-bromopyridine as precursors. Ultraviolet melting and DNase I footprinting studies indicate that the triplex stabilizing properties of 2′-modified MAPs are determined by the conformation of the entire oligonucleotide backbone. Me-MAP confers a higher triplex stability than 2′-deoxycytidine whereas triplex stabilization by MOE-MAP is similar to that of dC. Incorporation of Me-MAP or MOE-MAP into oligonucleotides renders them dramatically more resistant to degradation by serum nucleases than incorporation of 2-amino-3-methyl-5-(2′-deoxy-β-d-ribofuranosyl) pyridine (dMAP) or dC. © The Royal Society of Chemistry 2011. |
| spellingShingle | Lou, C Xiao, Q Tailor, R Ben Gaied, N Gale, N Light, M Fox, K Brown, T 2 '-Substituted 2-amino-3-methylpyridine ribonucleosides in triplex-forming oligonucleotides: triplex stability is determined by chemical environment |
| title | 2 '-Substituted 2-amino-3-methylpyridine ribonucleosides in triplex-forming oligonucleotides: triplex stability is determined by chemical environment |
| title_full | 2 '-Substituted 2-amino-3-methylpyridine ribonucleosides in triplex-forming oligonucleotides: triplex stability is determined by chemical environment |
| title_fullStr | 2 '-Substituted 2-amino-3-methylpyridine ribonucleosides in triplex-forming oligonucleotides: triplex stability is determined by chemical environment |
| title_full_unstemmed | 2 '-Substituted 2-amino-3-methylpyridine ribonucleosides in triplex-forming oligonucleotides: triplex stability is determined by chemical environment |
| title_short | 2 '-Substituted 2-amino-3-methylpyridine ribonucleosides in triplex-forming oligonucleotides: triplex stability is determined by chemical environment |
| title_sort | 2 substituted 2 amino 3 methylpyridine ribonucleosides in triplex forming oligonucleotides triplex stability is determined by chemical environment |
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