4-硝基苯基胸苷-5'-基碳酸酯 | 10270-37-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 4-硝基苯基胸苷-5'-基碳酸酯
• 英文名称: 4-nitrophenyl thymidine-5'-yl carbonate
• 英文别名: O^5'-(4-nitro-phenoxycarbonyl)-thymidine；(4-Nitrophenyl)-thymidin-5'-carbonat；5'-O-(4-Nitrophenyloxycarbonyl)-thymidine；[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl (4-nitrophenyl) carbonate
• CAS: 10270-37-8
• 化学式: C₁₇H₁₇N₃O₉
• 分子量: 407.337
• InChiKey: CMIREBUSPKIDRE-BFHYXJOUSA-N

物化性质

• 熔点：
  145-146 °C(Solv: ethyl acetate (141-78-6))
• 密度：
  1.511±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  160
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(3-hydroxy-2-(2-nitrophenyl)propyl)-9H-thioxanthen-9-one 、 4-硝基苯基胸苷-5'-基碳酸酯 在 4-二甲氨基吡啶 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以21%的产率得到T7S2-O(CO)Thy
  参考文献：
  名称：

  On the Mechanism of Intramolecular Sensitization of Photocleavage of the 2-(2-Nitrophenyl)propoxycarbonyl (NPPOC) Protecting Group

  摘要：

  A spectroscopic study of a variety of covalently linked thioxanthone(TX)-linker-2-(2-nitrophenyl)propoxycarbonyl(NPPOC)-substrate conjugates is presented. Herein, the TX chromophore functions as an intramolecular sensitizer to the NPPOC moiety, a photolabile protecting group used in photolithographic DNA chip synthesis. The rate of electronic energy transfer between TX and NPPOC was quantified by means of stationary fluorescence as well as nanosecond and femtosecond time-resolved laser spectroscopy. A dual mechanism of triplet-triplet energy transfer has been observed comprising a slower mechanism involving the Ti(pi pi*) state of TX with linker-length-dependent time constants longer than 20 ns and a fast mechanism with linker-length-dependent time constants shorter than 3 ns. Evidence is provided that the latter mechanism is due to energy transfer from the T-2(n pi*) state which is in fast equilibrium with the fluorescent S-1(pi pi*) state. In the case of direct linkage between the aromatic rings of TX and NPPOC, the spectroscopic properties are indicative of one united chromophore which, however, still shows the typical NPPOC cleavage reaction triggered by intramolecular hydrogen atom transfer to the nitro group.

  DOI：

  10.1021/ja072355p
• 作为产物：
  描述：

  对硝基苯基氯甲酸酯 、 beta-胸苷 在 吡啶 作用下， 以60%的产率得到4-硝基苯基胸苷-5'-基碳酸酯
  参考文献：
  名称：

  固相寡聚脱氧核苷酸合成：使用过氧阴离子脱保护的两步循环

  摘要：

  开发了一种新型固相亚磷酰胺基寡脱氧核苷酸两步合成方法。该方法的关键是用芳氧基羰基替换 5'-二甲氧基三苯甲基封闭基团，并使用 N-二甲氧基三苯甲基保护腺嘌呤和胞嘧啶的环外胺。通过这些修饰，每个 2'-脱氧核苷 3'-亚磷酰胺与固体支持物上生长的寡脱氧核苷酸偶联后，可以用缓冲在 pH 9.6 的过氧阴离子的水性混合物处理。该试剂有效去除碳酸酯保护基团，同时氧化亚磷酸酯核苷酸间键。因此，新的两步合成循环是可能的。

  DOI：

  10.1021/ja030376n

文献信息

• Method for covalently attaching nucleosides and/or nucleotides on surfaces and method for determining coupling yields in the synthesis of nucleotides
  申请人：Stengele Klaus-Peter

  公开号：US20060154256A1

  公开（公告）日：2006-07-13

  The present invention relates to a method for covalently attaching nucleosides and/or nucleotides on surfaces having reactive functional groups, where in a first step, the reactive functional groups are made to react with suitable derivatized nucleosides and/or nucleotides, and in a second step, they are converted with a protecting group reagent, so that a reaction product of the consecutive reaction interacts with electromagnetic radiation such that it can be quantitatively determined. The invention also relates to a method for determining the repetitive coupling yields in the synthesis of nucleotides where the free 3′ or 5′ hydroxy group of a selected nucleoside and/or nucleotide is converted with a compound of formula (I) where L is a common suitable leaving group, the motif O—PX represents a phosphor amidite, a H-phosphonate a phosphonic acid ester, a phosphotriester, Y═O or S, N is a nucleoside or a nucleotide derivative which subsequently reacts further with a protecting group reagent and the elimination of the leaving group (L), which is subsequently further eliminated. The quantity of the leaving group (L) eliminated in step b) is quantitatively determined in the form of its anion (L − ) by means of optical spectroscopy.

  本发明涉及一种在具有反应性功能团的表面上共价连接核苷和/或核苷酸的方法。其中，在第一步中，反应性功能团与适当衍生的核苷和/或核苷酸发生反应，在第二步中，它们与保护基试剂转化，使得连续反应的反应产物与电磁辐射相互作用，从而可以定量测定。该发明还涉及一种确定核苷酸合成中重复偶联收率的方法，其中选择的核苷和/或核苷酸的自由3'或5'羟基转化为化合物(I)的形式，其中L是一种常见的适当离去基，O-PX基序列代表磷酰胺、H-膦酸酯、磷酸酯、磷酸三酯，Y=O或S，N是一个核苷或核苷酸衍生物，随后进一步与保护基试剂反应，并消除离去基(L)，随后进一步消除。步骤b)中消除的离去基(L)的数量以其阴离子(L-)的形式通过光谱学定量测定。
• METHOD FOR COVALENTLY ATTACHING NUCLEOSIDES AND/OR NUCLEOTIDES ON SURFACES AND METHOD FOR DETERMINING COUPLING YIELDS IN THE SYNTHESIS OF NUCLEOTIDES
  申请人：Chemogenix GmbH

  公开号：EP1438322A2

  公开（公告）日：2004-07-21
• [EN] METHOD FOR COVALENTLY ATTACHING NUCLEOSIDES AND/OR NUCLEOTIDES ON SURFACES AND METHOD FOR DETERMINING COUPLING YIELDS IN THE SYNTHESIS OF NUCLEOTIDES<br/>[FR] PROCEDE DE FIXATION COVALENTE DE NUCLEOSIDES ET/OU NUCLEOTIDES SUR DES SURFACES, ET PROCEDE DE DETECTION DE RENDEMENTS DE COUPLAGE DANS LA SYNTHESE DE NUCLEOTIDES
  申请人：CHEMOGENIX GMBH

  公开号：WO2003035664A2

  公开（公告）日：2003-05-01

  The present invention relates to a method for covalently attaching nucleosides and/or nucleotides on surfaces having reactive functional groups, where in a first step, the reactive functional groups are made to react with suitable derivatized nucleosides and/or nucleotides, and in a second step, they are converted with a protecting group reagent, so that a reaction product of the consecutive reaction interacts with electromagnetic radiation such that it can be quantitatively determined. The invention also relates to a method for determining the repetitive coupling yields in the synthesis of nucleotides where the free 3' or 5' hydroxy group of a selected nucleoside and/or nucleotide is converted with a compound of formula (I), where L is a common suitable leaving group, the motif O-PX represents a phosphor amidite, a H-phosphonate a phosphonic acid ester, a phosphotriester, Y = O or S, N is a nucleoside or a nucleotide derivative which subsequently reacts further with a protecting group reagent and the elimination of the leaving group (L), which is subsequently further eliminated. The quantity of the leaving group (L) eliminated in step b) is quantitatively determined in the form of its anion (L-) by means of optical spectroscopy.
• [EN] METHOD FOR THE INTRAMOLECULAR ENERGY TRANSFER FOR THE CLEAVAGE OF LABILE FUNCTIONAL GROUP FROM BIOMOLECULES AND THE PROTECTED BIOMOLECULES<br/>[FR] PROCEDE DE TRANSFERT D'ENERGIE INTRAMOLECULAIRE UTILISE POUR LE CLIVAGE DE GROUPES FONCTIONNELS LABILES HORS DE BIOMOLECULES ET BIOMOLECULES PROTEGEES
  申请人：STEINER ULRICH

  公开号：WO2004089529A1

  公开（公告）日：2004-10-21

  The present invention provides a chemical compound and a method for the cleavage of labile functional groups from molecules by the interaction of electromagnetic radiation by the use of the chemical compound. Further, the invention provides a method for the manufacture of DNA chips by spatially addressed light directed nucleotide synthesis on solid substrates. The cleavage of the labile functional group is achieved by intramolecular energy transfer of the excitation energy.
• Solid-Phase Oligodeoxynucleotide Synthesis:  A Two-Step Cycle Using Peroxy Anion Deprotection
  作者：Agnieszka B. Sierzchala、Douglas J. Dellinger、Jason R. Betley、Tadeusz K. Wyrzykiewicz、Christina M. Yamada、Marvin H. Caruthers

  DOI：10.1021/ja030376n

  日期：2003.11.1

  phosphoramidite based oligodeoxynucleotide two-step synthesis method has been developed. Keys to this method are replacement of the 5'-dimethoxytrityl blocking group with an aryloxycarbonyl and the use of N-dimethoxytrityl protection for the exocyclic amines of adenine and cytosine. With these modifications, coupling of each 2'-deoxynucleoside 3'-phosphoramidite to the growing oligodeoxynucleotide

  开发了一种新型固相亚磷酰胺基寡脱氧核苷酸两步合成方法。该方法的关键是用芳氧基羰基替换 5'-二甲氧基三苯甲基封闭基团，并使用 N-二甲氧基三苯甲基保护腺嘌呤和胞嘧啶的环外胺。通过这些修饰，每个 2'-脱氧核苷 3'-亚磷酰胺与固体支持物上生长的寡脱氧核苷酸偶联后，可以用缓冲在 pH 9.6 的过氧阴离子的水性混合物处理。该试剂有效去除碳酸酯保护基团，同时氧化亚磷酸酯核苷酸间键。因此，新的两步合成循环是可能的。