3'-deoxy-3'-O-[(carboxymethyl)oxo]thymidine | 38934-60-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3'-deoxy-3'-O-[(carboxymethyl)oxo]thymidine
• 英文别名: 3'-O-(carboxymethyl)thymidine；3'-O-carboxymethylthymidine；thymidin-3'-yloxy-acetic acid；3'-O-(Carboxymethyl)thymidin；3'-O-Carboxymethyl-thymidin；2-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyacetic acid
• CAS: 38934-60-0
• 化学式: C₁₂H₁₆N₂O₇
• 分子量: 300.268
• InChiKey: UGGFAVYFKYAKJM-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  保护胸苷 在 sodium hydride 作用下， 以 溶剂黄146 为溶剂， 反应 23.0h， 生成 3'-deoxy-3'-O-[(carboxymethyl)oxo]thymidine
  参考文献：
  名称：

  光化学释放受保护的含有3'-乙醇酸末端的寡核苷酸

  摘要：

  使用邻硝基苄基分子内光化学氧化还原反应，从固相支持物中释放出适于进一步加工的含有3'-乙醇酸末端的受保护的寡核苷酸。在先前已证明形成少于2％的胸腺嘧啶·胸腺嘧啶光二聚体的条件下，长度介于12至20个核苷酸之间的可变序列的分离寡核苷酸的产率在45％至79％之间。

  DOI：

  10.1016/0040-4020(94)00946-r

文献信息

• Phosphinoamidite carboxylates and analogs thereof in the synthesis of oligonucleotides having reduced internucleotide charge
  申请人：——

  公开号：US20040116687A1

  公开（公告）日：2004-06-17

  Nucleoside phosphinoamidite carboxylates and analogs are provided that have the structure of formula (III) 1 wherein A is hydrogen, hydroxyl, lower alkoxy, lower alkoxy-substituted lower alkoxy, halogen, SH, NH 2 , azide or DL wherein D is O, S or NH and L is a heteroatom-protecting group, unsubstituted hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, or substituted heteroatom-containing hydrocarbyl; B is a nucleobase; and one of R 11 and R 12 is a blocking group and the other is (IV) or (VI) 2 in which W, X, Y, Z, R 1 and n are as defined herein.

  提供了具有公式（III）结构的核苷酸磷酰胺羧酸酯和类似物，其中A为氢、羟基、低烷氧基、低烷氧基取代的低烷氧基、卤素、SH、NH2、偶氮基或DL，其中D为O、S或NH，L为杂原子保护基、未取代的烃基、取代的烃基、含杂原子的烃基或取代的含杂原子的烃基；B为核苷碱基；R11和R12中的一个是阻断基，另一个是（IV）或（VI），其中W、X、Y、Z、R1和n如此定义。
• Phosphinoamidite Carboxylates and Analogs Thereof in the Synthesis of Oligonucleotide Having Reduced Internucleotide Charge
  申请人：DELLINGER DOUGLAS J.

  公开号：US20100311960A1

  公开（公告）日：2010-12-09

  Nucleoside phosphinoamidite carboxylates and analogs are provided that have the structure of formula (III) wherein A is hydrogen, hydroxyl, lower alkoxy, lower alkoxy-substituted lower alkoxy, halogen, SH, NH 2 , azide or DL wherein D is O, S or NH and L is a heteroatom-protecting group, unsubstituted hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, or substituted heteroatom-containing hydrocarbyl; B is a nucleobase; and one of R 11 and R 12 is a blocking group and the other is (IV) or (VI) in which W, X, Y, Z, R 1 and n are as defined herein.

  提供了具有公式（III）结构的核苷酸磷酸酰胺羧酸酯和类似物，其中A是氢、羟基、较低的烷氧基、较低的烷氧基取代的较低的烷氧基、卤素、SH、NH2、偶氮基或DL，其中D是O、S或NH，L是杂原子保护基、未取代的烃基、取代的烃基、含杂原子的烃基或取代的含杂原子的烃基；B是核碱基；R11和R12中的一个是阻断基，另一个是（IV）或（VI），其中W、X、Y、Z、R1和n如本文所定义。
• 3′-Oxo-, amino-, thio- and sulfone-acetic acid modified thymidines: Effect of increased acidity on ribonuclease A inhibition
  作者：Dhrubajyoti Datta、Anirban Samanta、Swagata Dasgupta、Tanmaya Pathak

  DOI：10.1016/j.bmc.2013.05.047

  日期：2013.8

  A family of 3'-functionalized thymidines carrying XCH2COOH (X = O, NH, S, SO2) groups has been designed as inhibitors of RNase A. This is because it is possible to manipulate the overall acidity of this new class of nucleic 'acids' by changing X from oxygen to the SO2 group in the series. It is also expected that the acyclic nature of the XCH2COOH group would provide enough flexibility to the -COOH group to have maximum interactions with the catalytic subsite P-1 of RNase A. As the -SO2CH2COOH substituted derivative showed better potency partially because of the increased acidity of the -COOH group, the inhibitory properties of both 5'-substituted and 3',5'-disubstituted sulfone acetic acid modified thymidines were investigated. Two -SO2CH2COOH groups were incorporated with the expectation of targeting two phosphate binding sites simultaneously. Thus, 3',5'-dideoxy-3',5'-bis-S-[(carboxymethyl)sulfonyl]thymidine emerged as the best inhibitor in this series with a K-i value of 25 +/- 2 mu M. (C) 2013 Elsevier Ltd. All rights reserved.
• EP1334111A4
  申请人：——

  公开号：EP1334111A4

  公开（公告）日：2007-01-24
• PHOSPHINOAMIDITE CARBOXYLATES AND ANALOGS THEREOF IN THE SYNTHESIS OF OLIGONUCLEOTIDES HAVING REDUCED INTERNUCLEOTIDE CHARGE
  申请人：Dellinger, Douglas J.

  公开号：EP1334111A2

  公开（公告）日：2003-08-13