디옥시우리딘
2""-데옥시우리딘 · 디옥시우리딘 · 2'-데옥시우리딘(2'-DEOXYURIDINE) · 2'-데옥시우리딘 · DU · deoxyuridine · 1-((2R,4S,5R)-4-Hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione · URACIL DEOXYRIBOSIDE
식별자 및 물리적 특성
| CAS No. | 951-78-0 |
|---|---|
| 분자식 | C9H12N2O5 |
| 평균 분자량 | 228.2 g/mol |
| 단동위원소 질량 | 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 |
| 현지명 | 디옥시우리딘 |
화학 및 물리적 성질
| XLogP | -1.6 |
|---|---|
| 극성 표면적 | 99.1 |
| 수소 결합 공여자 수 | 3 |
| 수소 결합 수용자 수 | 5 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 16 |
| 형식 전하 | 0 |
| 복잡도 | 343 |
| 녹는점 | 167-169 °C(lit.) |
| 끓는 점 | 370.01°C (rough estimate) |
| 밀도 | 1.3705 (rough estimate) |
| 굴절률 | 52 ° (C=1, 1mol/L NaOH) |
| 저장 조건 | Inert atmosphere,2-8°C |
| 용해도 | DMSO(약간 용해됨), 메탄올(약간 용해됨, 가열), 물(약간 용해됨) |
| 물리적 상태 | 가루 |
| pKa(산도 계수) | pKa 9.3(H2O t = 25) (Uncertain) |
| 색상 | 흰색에서 황백색까지 |
| 생물학적 소스 | synthetic (organic) |
| 용해도 | 300 g/L (20 ºC) |
| 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 |
| EPA | Uridine, 2'-deoxy- (951-78-0) |
화학적 성질
White crystalline powder
안전 및 규제
| 수질 위해 등급(WGK) | 3 |
|---|---|
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | YU7490000 |
| 관세 코드 | 29349990 |
| 위험 문구(R) | 36/37/38 |
| 위험 표시 | Xn |
| 안전 문구(S) | 22-24/25-37/39-36/37/39-26 |
| F 고인화성물질 | 10-23 |
| 위험 참고 사항 | Air Sensitive |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
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.
용도
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.