1-Methyl-thymin | 6299-61-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-Methyl-thymin
• 英文别名: 1,5-Dimethyldihydropyrimidine-2,4(1h,3h)-dione；1,5-dimethyl-1,3-diazinane-2,4-dione
• CAS: 6299-61-2
• 化学式: C₆H₁₀N₂O₂
• 分子量: 142.158
• InChiKey: KKMULICUOLXREQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Methyl-thymin 在 溴 、 溶剂黄146 作用下， 生成 1-甲基脲嘧啶
  参考文献：
  名称：

  Synthesis of 1-Substituted Thymines

  摘要：

  DOI：

  10.1021/jo01084a625
• 作为产物：
  描述：

  1-甲基脲嘧啶 在 氢气 作用下， 生成 1-Methyl-thymin
  参考文献：
  名称：

  转移氢化作为核苷酸中的氧化还原过程

  摘要：

  使用理论和实验相结合的策略，已确定了核苷酸碱基尿嘧啶，胸腺嘧啶，胞嘧啶，腺嘌呤和鸟嘌呤的氢化热。最容易氢化的碱基是尿嘧啶，其次是胸腺嘧啶和胞嘧啶。这些氢化焓与糖模型衍生的酮和醛的氢化焓的比较表明，寡核苷酸中尿嘧啶和糖磷酸主链之间存在近乎中性的氢转移。

  DOI：

  10.1021/jp507855k

文献信息

• Stereoisomeric C5−C5‘-Linked Dihydrothymine Dimers Produced by Radiolytic One-Electron Reduction of Thymine Derivatives in Anoxic Aqueous Solution:  Structural Characteristics in Reference to Cyclobutane Photodimers
  作者：Takeo Ito、Hideki Shinohara、Hiroshi Hatta、Sei-ichi Nishimoto

  DOI：10.1021/jo990059s

  日期：1999.7.1

  Radiolytic one-electron reduction of 1-methylthymine (1a) and 1,3-dimethylthymine (1b) in anoxic aqueous solution afforded stereoisomeric C5-C5'-linked dihydrothymine dimers, fractionated into the meso forms of (5R,5'S)- and (5S,5'R)-bi-5,6-dihydrothymine (3a,b[meso]) and a racemic mixture of (5R,5'R)- and (5S,5'S)-bi-5,6-dihydrothymines (3a,b[rac]), along with 5,6-dihydrothymines (2a,b). The meso

  1-甲基胸腺嘧啶 (1a) 和 1,3-二甲基胸腺嘧啶 (1b) 在缺氧水溶液中的辐射单电子还原得到立体异构的 C5-C5'-连接的二氢胸腺嘧啶二聚体，分馏成 (5R,5'S)- 和 ( 5S,5'R)-bi-5,6-dihydrothymine (3a,b[meso]) 和 (5R,5'R)- 和 (5S,5'S)-bi-5,6-dihydrothymines 的外消旋混合物（ 3a,b[rac])，以及 5,6-二氢胸腺嘧啶 (2a,b)。内消旋和外消旋二聚体的产量几乎相等，与顺式-syn-环丁烷嘧啶光二聚体具有结构相似性，顺式-syn-环丁烷嘧啶光二聚体被确定为紫外线诱导的高度诱变和致癌光损伤。胸苷 (1c) 的类似辐射解单电子还原导致 (5R,5'S)- 和 (5S,5'R)-bi-5,6-二氢胸苷 (3c[RS]) 和两种非对映异构体的拟内消旋形式(5R,5' R)-和 (5S,5'S)-双-5
• PNA monomer and precursor
  申请人：Panagene, Inc.

  公开号：EP2174936A1

  公开（公告）日：2010-04-14

  This application relates to monomers of the general formula (I) for the preparation PNA (peptide nucleic acid) oligomers and provides method for the synthesis of both predefined sequence PNA oligomers and random sequence PNA oligomers: (I) wherein E is nitrogen or C-R'; J is sulfur or oxygen; R', R1, R2, R3, R4 is independently H, halogen, alkyl, nitro, nitrile, alkoxy, halogenated alkyl, halogenated alkoxy, phenyl or halogenated phenyl, R5 is H or protected or unprotected side chain of natural or unnatural a-amino acid; and B is a natural or unnatural nucleobase, wherein when said nucleobase has an exocyclic amino function, said function is protected by protecting group which is labile to acids but stable to weak to medium bases in the presence of thiol.

  本申请涉及用于制备 PNA（肽核酸）寡聚体的通式（I）单体，并提供了预定序列 PNA 寡聚体和随机序列 PNA 寡聚体的合成方法：(I) 其中 E 是氮或 C-R'；J 是硫或氧；R'、R1、R2、R3、R4 独立地是 H、卤素、烷基、硝基、腈基、烷氧基、卤代烷基、卤代烷氧基、苯基或卤代苯基；R5 是 H 或天然或非天然 a-氨基酸的受保护或未受保护侧链；B 是天然或非天然核碱基，其中当所述核碱基具有外环氨基功能时，所述功能受保护基团保护，该保护基团对酸不稳定，但在硫醇存在下对弱碱至中碱稳定。
• Radiation-Induced and Photosensitized Splitting of C5−C5‘-Linked Dihydrothymine Dimers:  Product and Laser Flash Photolysis Studies on the Oxidative Splitting Mechanism
  作者：Takeo Ito、Hideki Shinohara、Hiroshi Hatta、Sei-ichi Nishimoto、Shin-ichi Fujita

  DOI：10.1021/jp991877r

  日期：1999.10.1

  Radiation-induced and photosensitized one-electron oxidation of stereoisomeric CS-CS'-linked dihydrothymine dimers (1a,b[meso], meso compound of (5R,5'S)-bi-5,6-dihydrothymine; la,b[rac], racemic compound of (5R,5'R)- and (5S,5'S)-bi-5,6-dihydrothymines), which are the major products yielded by radiolytic reduction of 1-methylthymine (2a) and 1,3-dimethylthymine (2b) in aqueous solution, was studied to compare with the photoreactivating repair mechanism of cyclobutane pyrimidine photodimers. Reacting with sulfate radical anion (SO4.-), azide radical (N-3(.)), Or photoexcited anthraquinone-2-sulfonate (AQS) as oxidants, the C5-C5'-linked dihydrothymine dimers la,b split to regenerate the corresponding thymine monomers 2a,b along with 5,6-dihydrothymines (3a,b) in a pH dependent manner. The transient absorption spectra of 5,6-dihydrothymin-5-yl radicals (6a,b) were observed in the nanosecond laser flash photolysis of 1a,b in phosphate buffer under conditions of SO4.- generation. Both the product study and the laser flash photolysis study indicated an oxidative splitting mechanism by which one-electron oxidation of the C5-C5'-linked dimers la,b produces the radical cation intermediates (4a,b), which undergo facile fragmentation into 5,6-dihydrothymin-5-yl radicals 6a,b and CS-cations (5a,b), followed by deprotonation at C6 of 5a,b to regenerate the monomers 2a,b.
• Radiation-Induced and Photosensitized Splitting of C5−C5‘-Linked Dihydrothymine Dimers. 2. Conformational Effects on the Reductive Splitting Mechanism
  作者：Takeo Ito、Hideki Shinohara、Hiroshi Hatta、Shin-ichi Fujita、Sei-ich Nishimoto

  DOI：10.1021/jp9939367

  日期：2000.4.1

  Radiation-induced and photosensitized reductive splitting of stereoisomeric C5-C5'-linked dihydrothymine dimers (la,b [meso], meso compound of (5R,5'S)- and (5S,5'R)-bi-5,6-dihydrothymines; 1a,b [rac], racemic compound of (5R,5'R)- and (5S,5'S)-bi-5, 6-dihydrothymines) in aqueous solution were studied to compare with the one-electron oxidative splitting mechanism and the photorepair reaction of cyclobutane pyrimidine photodimers. Reacting with radiation-chemically and photochemically generated hydrated electrons or with photoexcited reduced form of flavin adenine dinucleotide (*FADH(-)), the C5-C5'-linked dihydrothymine dimers la,b produced the corresponding 5,6-dihydrothymine derivatives (3a,b) along with the thymine monomers (2a,b) in minor yields. Both the product and laser flash photolysis studies indicated that one-electron adducts of the C5-C5'-linked dimers la,b undergo C5-C5'-bond cleavage to generate the 5,6-dihydrothymin-5-yl radicals (5a,b) and the 5,6-dihydrothymine CS-anions (6a,b) resulting in the formation of 3a,b by facile protonation at C5. In the reduction by *FADH-, splitting of the 5,6-dihydro-1-methylthymine dimer 1a[meso] into the monomer 2a was more efficient than that of the racemic isomer 1a[rac]. Conformational analysis by NMR of la[meso] and la[rac] in solution suggested that la[meso] may favor a "closed-shell" conformation and undergo one-electron reduction to Form 5a and 6a, whereas la[rac] may be in a "opened-shell" conformation and undergo successive two-electron reduction by "FADH(-) to produce 2 equiv of 6a as a precursor of 3a.
• NUCLEIC ACID BINDING COMPOUNDS CONTAINING PYRAZOLO¬3,4-D PYRIMIDINE ANALOGUES OF PURIN-2,6-DIAMINE AND THEIR USES
  申请人：Roche Diagnostics GmbH

  公开号：EP1307469B1

  公开（公告）日：2008-01-23