2'-デオキシウリジン
2'-デオキシウリジン · デオキシウリジン · デスオキシリボースウラシル · ウラシルデオキシリボシド · 5-デメチルチミジン · 2-デオキシウリジン · 2′‐デオキシウリジン · (+)-2'-デオキシウリジン
識別子と物理属性
| CAS No. | 951-78-0 |
|---|---|
| 分子式 | C9H12N2O5 |
| 平均分子量 | 228.2 g/mol |
| 単同位体質量 | 228.07462149 g/mol |
| SMILES | O=c1ccn(C2CC(O)C(CO)O2)c(=O)[nH]1 |
| InChIKey | MXHRCPNRJAMMIM-UHFFFAOYSA-N |
| PubChem CID | 640 |
| DTXSID | DTXSID60862484 |
| 現地名 | 2'-デオキシウリジン |
化学・物理的性質
| XLogP | -1.6 |
|---|---|
| 極性表面積 | 99.1 |
| 水素結合供与体数 | 3 |
| 水素結合受容体数 | 5 |
| 回転可能結合数 | 2 |
| 重原子数 | 16 |
| 形式電荷 | 0 |
| 複雑度 | 343 |
| 融点 | 167-169 °C(lit.) |
| 比旋光度 | D22 +50° (c = 1.1 in N NaOH) |
| 沸点 | 370.01°C (rough estimate) |
| 密度 | 1.3705 (rough estimate) |
| 屈折率 | 52 ° (C=1, 1mol/L NaOH) |
| 貯蔵条件 | Inert atmosphere,2-8°C |
| 溶解度 | DMSO（微量）、メタノール（微量、加温）、水（微量）300g/L(20℃) |
| 外観・状態 | 粉 |
| pKa（酸解離定数） | pKa 9.3(H2O t = 25) (Uncertain) |
| 色 | ホワイトからオフホワイト |
| 由来生物 | synthetic (organic) |
| Merck | 14,2910 |
| BRN | 24433 |
| InChI | 1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1 |
| InChIKey | MXHRCPNRJAMMIM-ATRFCDNQSA-N |
| SMILES | OC[C@H]1O[C@H](C[C@@H]1O)N2C=CC(=O)NC2=O |
| CAS データベース | 951-78-0(CAS DataBase Reference) |
| EPAの化学物質情報 | Uridine, 2'-deoxy- (951-78-0) |
化学的特性
White crystalline powder
安全性と法規制
| F | 10-23 |
|---|---|
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | YU7490000 |
| 税関コード | 29349990 |
| 危険文句（R） | 36/37/38 |
| 化審法 | (9)-2228 |
| 危険表示 | Xn |
| hazard_note | Air Sensitive |
| 安全措置（S） | 22-24/25-37/39-36/37/39-26 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
用途
核酸関連研究用。
説明
2'-Deoxyuridine is an intermediate in the synthesis of thymidylate, which is a precursor for DNA synthesis. It has been shown to inhibit the enzymatic activity of enzymes responsible for synthesizing uridine and thymidylate, leading to neuronal death. 2'-Deoxyuridine has been used as a fluorescence probe for nucleic acids and as a polymerase chain reaction (PCR) substrate. It is also known to bind with toll-like receptor 4 (TLR4), which is involved in inflammatory responses.
使用
2'-Deoxyuridine is frequently halogenated to create thymidine analogues useful for studies of DNA synthesis and degradation mechanisms. Derivatized 2'-Deoxyuridines used as labeling substrates include chloro-2'-deoxyuridine (CldU), bromodeoxyuridine (BrdU) and/or iododeoxyuridine (IdU). Other useful analogues of 2'-deoxyuridine include 5-ethynyl-2'-deoxyuridine (DdU) and 5-hydroxymethyl-2'-deoxyuridine (HmdU). Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies. Deoxyuridine (dU) is used to indirectly determine if there are sufficient levels of folate and cobalamin in cell or tissue samples.