کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
10593170 981804 2012 4 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Structural requirements for hybridization at the 5′-position are different in α-l-LNA as compared to β-d-LNA
کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Structural requirements for hybridization at the 5′-position are different in α-l-LNA as compared to β-d-LNA
چکیده انگلیسی
The synthesis and biophysical evaluation of R and S-5′-Me-α-l-LNA nucleoside phosphoramidites and modified oligo-2′-deoxyribonucleotides is reported. Synthesis of the nucleoside phosphoramidites was accomplished in multi-gram quantities starting from diacetone glucose. The 5′-methyl group in the S configuration was introduced by reacting the sugar 5′-aldehyde with MeMgBr. Synthesis of the R-5′-Me isomer was accomplished from the S-5′-Me nucleoside by a late stage inversion using Mitsunobu conditions. Evaluation of the modified oligonucleotides in thermal denaturation experiments revealed that R-5′-Me-α-l-LNA showed similar RNA affinity as α-l-LNA while the S-5′-Me analog was less stabilizing. This result is in contrast to the β-d-series where the S-5′-Me isomer showed LNA-like affinity for RNA while the R-5′-Me group completely reversed the stabilization effect on duplex thermostability.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Bioorganic & Medicinal Chemistry Letters - Volume 22, Issue 1, 1 January 2012, Pages 296-299
نویسندگان
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