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 5â²-position are different in α-l-LNA as compared to β-d-LNA
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
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چکیده انگلیسی
The synthesis and biophysical evaluation of R and S-5â²-Me-α-l-LNA nucleoside phosphoramidites and modified oligo-2â²-deoxyribonucleotides is reported. Synthesis of the nucleoside phosphoramidites was accomplished in multi-gram quantities starting from diacetone glucose. The 5â²-methyl group in the S configuration was introduced by reacting the sugar 5â²-aldehyde with MeMgBr. Synthesis of the R-5â²-Me isomer was accomplished from the S-5â²-Me nucleoside by a late stage inversion using Mitsunobu conditions. Evaluation of the modified oligonucleotides in thermal denaturation experiments revealed that R-5â²-Me-α-l-LNA showed similar RNA affinity as α-l-LNA while the S-5â²-Me analog was less stabilizing. This result is in contrast to the β-d-series where the S-5â²-Me isomer showed LNA-like affinity for RNA while the R-5â²-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
Journal: Bioorganic & Medicinal Chemistry Letters - Volume 22, Issue 1, 1 January 2012, Pages 296-299
نویسندگان
Punit P. Seth, Charles R. Allerson, Michael E. Ãstergaard, Eric E. Swayze,