尿嘧啶-D1 | 24897-51-6

• 物质功能分类: 医药中间体 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 尿嘧啶-D1
• 英文名称: <6-(2)H>-uracil
• 英文别名: <6-2H>uracil；uracil-6-d；6-deuterio-1H-pyrimidine-2,4-dione；4D-Uracil；Uracil-6-D1；6-deuterio-1H-pyrimidine-2,4-dione
• CAS: 24897-51-6
• 化学式: C₄H₄N₂O₂
• 分子量: 113.08
• InChiKey: ISAKRJDGNUQOIC-VMNATFBRSA-N

物化性质

• 熔点：
  320-322 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  尿嘧啶-D1 在 重水 作用下， 生成 1,3,4-D3-Uracil
  参考文献：
  名称：

  Nucleic acid bases studied by matrix isolation vibrational spectroscopy: Uracil and deuterated uracils

  摘要：

  DOI：

  10.1016/0584-8539(84)80073-2
• 作为产物：
  描述：

  1,3,4-D3-Uracil 在 水 作用下， 生成 尿嘧啶-D1
  参考文献：
  名称：

  Nucleic acid bases studied by matrix isolation vibrational spectroscopy: Uracil and deuterated uracils

  摘要：

  DOI：

  10.1016/0584-8539(84)80073-2

文献信息

• Stereochemistry of catabolism of the RNA base uracil
  作者：David Gani、Douglas W. Young

  DOI：10.1039/p19850001355

  日期：——

  A mammalian enzyme system has been used to study the stereochemistry of the catabolism of the pyrimidine uracil (1) to the amino acid β-alanine (4). Use of [5-2H]- and [6-2H]-uracils and of 2H2O in the incubations yielded stereospecifically deuteriated samples of β-alanine. Assays, involving total synthesis of samples of β-alanine unambiguously labelled with deuterium in each of the four C–H bonds

  哺乳动物酶系统已用于研究嘧啶尿嘧啶（1）分解为氨基酸β-丙氨酸（4）的立体化学。在培养中使用[5- 2 H]-和[6- 2 H]-尿嘧啶和2 H 2 O产生β-丙氨酸的立体特异性氘化样品。测定法，涉及β丙氨酸在四个C-H键的氘明确地标记的样本的总合成已经显示的是，在分解代谢过程中的第一步，尿嘧啶是通过二氢脱氢酶降低与整体抗加入氢气，在SI在C-6面和SI面在C-5。
• Stereochemistry of the dihydrouracil dehydrogenase reaction in metabolism of uracil to β-alanine
  作者：David Gani、Douglas W. Young

  DOI：10.1039/c39830000576

  日期：——

  Samples of β-alanine stereospecifically labeled with deuterium in each of the four C–H bonds have been synthesized; these been used to show that, in the first step of uracil metabolism, the pyrimidine is reduced by dihydrouracil dehydrogenase with overall trans-addition of hydrogen at the si-face at C-6 and the si-face at C-5.

  已经合成了在四个C–H键的每一个中均被氘标记的β-丙氨酸样品。这些被用于表明，在尿嘧啶代谢的第一步，嘧啶通过与整体二氢尿嘧啶脱氢酶降低反式在氢的-addition SI面取向在C-6和SI面取向在C-5。
• Mechanistic Studies of Antibody-Catalyzed Pyrimidine Dimer Photocleavage
  作者：John R. Jacobsen、Andrea G. Cochran、James C. Stephans、David S. King、Peter G. Schultz

  DOI：10.1021/ja00125a004

  日期：1995.5

  An antibody elicited against the trans, syn uracil cyclobutane dimer hapten 1 catalyzes the light-dependent cleavage of uracil dimers 1 and 2 to the corresponding monomers 3 and 4. Kinetic analysis of the antibody-catalyzed reaction affords a value of k(cat)/K-M = 1.7 x 10(3) M(-1) min(-1) for substrate 2, and comparison to the uncatalyzed reaction gives a rate acceleration of k(cat)/k(uncat) = 380. The wavelength dependence of the reaction and fluorescence quenching behavior suggest that a tryptophan residue is acting as a photosensitizer. The reaction mechanism was probed by measurement of secondary deuterium isotope effects. Substrates with selective deuterium substitutions in the cyclobutane ring were prepared, and isotope effects were measured by the method of internal competition using electrospray-ionization mass spectrometry to quantify the products. Kinetic isotope effects of (alpha-D)(V/K) = 1.11, 1.14, and 1.20 were observed for the 5,5'-, 6,6'-, and 5,5',6,6'-labeled substrates, respectively. These results are comparable to those observed in a similar study on the E. coli enzyme DNA photolyase(1) and suggest that the reaction may proceed via a radical anion intermediate with concerted breakage of the 5,5' and 6,6' bonds, Alternatively the reaction may proceed via a mechanism in which the first bond is cleaved in a reversible fashion.