DMT-2′Fluoro-dU Phosphoramidite

DMT-2′Fluoro-dU Phosphoramidite 구조식 이미지
카스 번호:
146954-75-8
상품명:
DMT-2′Fluoro-dU Phosphoramidite
동의어(영문):
2‘-F-U amidite;2'-Fluoro-dU CEP;2’-F-dU Amidite;2’-F-rUPhosphoramidite;2'-F-U Phosphoramidite;2'-F-dU Phosphoramidite;5'-O-DMT-2'-fluoro-dU-CE;5'-O-DMT-2'-F-dU-3'-CEDPA;2'-Fluoro Uridine Amidite;DMT-2'-F-U Phosphoramidite
CBNumber:
CB8500324
분자식:
C39H46FN4O8P
포뮬러 무게:
748.78
MOL 파일:
146954-75-8.mol
MSDS 파일:
SDS

DMT-2′Fluoro-dU Phosphoramidite 속성

저장 조건
Sealed in dry,Store in freezer, under -20°C
물리적 상태
가루
산도 계수 (pKa)
9.39±0.10(Predicted)
색상
흰색에서 황백색까지
InChIKey
HQHQPAYRJJMYQX-YOKGOYKLNA-N
SMILES
N1(C=CC(=O)NC1=O)[C@@H]1O[C@H](COC(C2=CC=CC=C2)(C2C=CC(=CC=2)OC)C2=CC=C(C=C2)OC)[C@@H](OP(OCCC#N)N(C(C)C)C(C)C)[C@H]1F |&1:8,10,36,51,r|

안전

WGK 독일 3

DMT-2′Fluoro-dU Phosphoramidite C화학적 특성, 용도, 생산

정의

DMT-2′Fluoro-dU Phosphoramidite is also known as 2'-F-U CE-Phosphoramidite. 2'-F-RNA oligonucleotides adopt an A-form helix on hybridisation to a target. Whereas a hydroxyl group of RNA is a hydrogen bond donor, fluorine appears to be a weak acceptor. These features of 2'-F-RNA oligonucleotides lead to certain interesting properties. For example, it was demonstrated that oligonucleotides hybridise to a RNA oligonucleotide in the following order of increasing stability: DNA < RNA < 2'-OMe-RNA < 2'-F-RNA

Synthesis

5'-O-(4,4'-Dimethoxytrityl)-2'-deoxy-2'-fluorouridine (3.00 g, 5.47 mmol) was dissolved in anhydrous dichloromethane (50 ml) under an argon atmosphere, N,N-diisopropylethylamine (0.55 ml,3.18 mmol), 1H-tetrazole (0.45 g, 6.45 mmol) and 2-cyanoethyl-N,N,N',N'-tetraisopropylphosphordiamidite (1.92 g, 6.36mmol) were added. And the mixture was stirred at room temperature overnight. The completion of the reaction was confirmed, 5 percent aqueous sodium hydrogen carbonate solution (20 ml) was added to the reaction mixture to allow layer separation, and the organic layer was washed with saturated brine (20 ml). The organic layer was dried over sodium sulfate, the filtrate was concentrated and the obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=75:25 - 30/70(v/v), containing 3percent triethylamine). The object fractions were collected and concentratedto give DMT-2′Fluoro-dU Phosphoramidite (2.76 g, 67.3 percent).

DMT-2′Fluoro-dU Phosphoramidite 준비 용품 및 원자재

원자재

준비 용품


DMT-2′Fluoro-dU Phosphoramidite 공급 업체

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