مورد إلكتروني
Substituted 1,8-naphthyridin-2(1H)-ones are superior to thymine in the recognition of adenine in duplex as well as triplex structures
| العنوان: | Substituted 1,8-naphthyridin-2(1H)-ones are superior to thymine in the recognition of adenine in duplex as well as triplex structures |
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| المصدر: | Eldrup , A B , Christensen , C , Haaima , G & Nielsen , P E 2002 , ' Substituted 1,8-naphthyridin-2(1H)-ones are superior to thymine in the recognition of adenine in duplex as well as triplex structures ' , Journal of the American Chemical Society , vol. 124 , no. 13 , pp. 3254-62 . |
| بيانات النشر: | 2002-04-03 |
| تفاصيل مُضافة: | Eldrup, Anne B Christensen, Caspar Haaima, Gerald Nielsen, Peter E. |
| نوع الوثيقة: | Electronic Resource |
| مستخلص: | The synthesis and evaluation of a series of novel nucleobases based on substituted 1,8-naphthyridin-2(1H)-ones are reported. The nucleobases were designed to meet the requirements for incorporation into peptide nucleic acids (PNAs) and were evaluated as part of PNA duplex and triplex nucleic acid recognition systems. Of the various nucleobases tested, only the 7-chloro-1,8-naphthyridin-2(1H)-one (7-Cl-bT) nucleobase led to consistently increased affinity in all recognition systems, duplex (Watson-Crick) as well as triplex (Hoogsteen). For multiply modified systems, the increase in thermal stability per modification was dependent on the sequence context, ranging from 2.0 degrees C (in separate positions) to 3.5 degrees C (in adjacent positions) in PNA-DNA duplexes and from 1.2 degrees C (in separate positions) to 3.2 degrees C (in adjacent positions) in PNA-RNA duplexes. Singly mismatched oligonucleotide targets were employed to demonstrate uncompromised sequence discrimination. When part of multiply modified triplex (Hoogsteen) recognition systems, the 7-Cl-bT unit gave rise to increases in the thermal stability ranging from 2.7 to 3.5 degrees C when incorporated into separated and adjacent positions, respectively. Our results furthermore indicate that the duplex stabilization is predominantly enthalpic and therefore most likely not a consequence of single-strand preorganization. Finally, and most surprisingly, we find no direct correlation between the end-stacking efficiency of this type of nucleobase and its helix stabilization when involved in Watson-Crick base pairing within a helix. |
| مصطلحات الفهرس: | Adenine/chemistry, Base Pairing, DNA/chemical synthesis, Naphthyridines/chemistry, Nucleic Acid Conformation, Peptide Nucleic Acids/chemical synthesis, RNA/chemical synthesis, Thermodynamics, Thymine/chemistry, article |
| URL: | |
| الإتاحة: | Open access content. Open access content info:eu-repo/semantics/closedAccess |
| ملاحظة: | English |
| أرقام أخرى: | DAV oai:pure.atira.dk:publications/d3b0aa14-5931-46e8-8886-0eacbfa087f6 1250464450 |
| المصدر المساهم: | UNIV OF COPENHAGEN From OAIster®, provided by the OCLC Cooperative. |
| رقم الأكسشن: | edsoai.on1250464450 |
| قاعدة البيانات: | OAIster |
| الوصف غير متاح. |