2-{2-[2-(2-azidoethoxy)ethoxy]ethoxymethyl}oxirane | 1233223-64-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-{2-[2-(2-azidoethoxy)ethoxy]ethoxymethyl}oxirane
• 英文别名: 2-[2-[2-(2-Azidoethoxy)ethoxy]ethoxymethyl]oxirane；2-[2-[2-(2-azidoethoxy)ethoxy]ethoxymethyl]oxirane
• CAS: 1233223-64-7
• 化学式: C₉H₁₇N₃O₄
• 分子量: 231.252
• InChiKey: SVXMQVPUDBLLRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-{2-[2-(2-azidoethoxy)ethoxy]ethoxymethyl}oxirane 在 碳酸氢钠 、 potassium carbonate 、 potassium hydrogencarbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 乙腈 为溶剂， 反应 76.5h， 生成 5-(prop-2-ynyl)carbamic acid 1-{2-[2-(2-tert-butoxycarbonylaminoethoxy)ethoxy]ethoxymethyl}-2-cyanoethyl ester 3'-O-(2-cyanoethyl)-2'-desoxyuridine
  参考文献：
  名称：

  Fluorescent Labeling of (Oligo)Nucleotides by a New Fluoride Cleavable Linker Capable of Versatile Attachment Modes

  摘要：

  The development of a fluoride cleavable linker 1 for reversibly labeling (oligo)nucleotides is described here. The linker allows different ways of chemical attachment of a reporter molecule, for example, click chemistry or amide formation. The versatile attachment modes of labels are demonstrated by derivatizations with pyrene and fluorescein. Besides the synthesis of the new linker, we also show the derivatization of iodobenzene as a model compound and a nucleoside to demonstrate the applicability. Further, cleavability studies in solution and on a solid-supported oligonucleotide are shown. The linker can be applied in the synthesis of reversible terminators, useful for new DNA sequencing technologies like cyclic reversibly terminating (CRT) sequencing.

  DOI：

  10.1021/bc900542f
• 作为产物：
  描述：

  3-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)propen-1-ene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以74 %的产率得到2-{2-[2-(2-azidoethoxy)ethoxy]ethoxymethyl}oxirane
  参考文献：
  名称：

  Spatiotemporal Investigation of Intercellular Heterogeneity via Multiple Photocaged Probes

  摘要：

  摘要 在正常生理环境和异常致病条件下，细胞间异质性广泛存在。为了破译异质性的原因和影响，人们多次尝试将时空信息与微环境中的细胞状态结合起来。此外，利用光笼/可光电激活的分子可以实现时空操纵。在这里，我们提供了一个平台，通过多个光笼式探针和自制光掩膜，对相邻细胞中不同的蛋白质表达进行时空分析。我们成功地建立了细胞间异质性（可光激活的 ROS 触发器），并绘制了目标（直接受 ROS 影响的细胞）和旁观者（周围的细胞）的图谱。在总蛋白组和半胱氨酸组中，旁观者细胞和目标细胞的蛋白质特征各不相同。我们的策略应能扩展时空图谱工具包，用于阐明细胞间的异质性。

  DOI：

  10.1002/chem.202301067

文献信息

• [EN] REVERSIBLE TERMINATORS FOR EFFICIENT SEQUENCING BY SYNTHESIS<br/>[FR] TERMINATEURS RÉVERSIBLES POUR UN SÉQUENÇAGE EFFICACE PAR SYNTHÈSE
  申请人：QUIATECH AB

  公开号：WO2008037568A2

  公开（公告）日：2008-04-03

  [EN] The invention relates to compounds of general structure (I) or salts thereof, wherein B is a nucleobase, X and Y independently are oxygen or sulphur, Z is a chemical group characterized by strong electron withdrawing properties, R1 is hydrogen, hydroxyl or a protected hydroxyl, R2 and R3 are together or separately hydrogen or a hydrocarbyl, R4 is hydrogen or a chemical moiety consisting of a linker molecule L, linking a detectable group to the rest of the structure (I), R5 is hydrogen or an additional electron withdrawing group. R5 can be identical with Z or different. R6 is hydrogen or a chemical moiety consisting of a linker unit L, a cleavable group and a detectable group joined together in the following order R6 = -L-cleavable group-detectable group. The detectable group is placed either on R4 or R6 or is absent, thus either R4 is hydrogen and the detectable group is placed on R6, or R6 is hydrogen and the detectable group is placed on R4, or both R4 and R6 are hydrogen. Numbers m and n are independently 0 or 1. Compounds of formula (I) are useful as reversible chain extension terminators. The invention also relates to the use of the compounds (I) in nucleic acid sequencing as well as to a method of preparing compounds of Formula (I).
  [FR] La présente invention concerne des composés de structure générale (I) ou des sels de ceux-ci, où B représente une base nucléotidique, X et Y représentent indépendamment oxygène ou soufre, Z représente un groupe chimique caractérisé par des propriétés de puissant électro-attracteur, R1 représente hydrogène, hydroxyle ou un hydroxyle protégé, R2 et R3 représentent conjointement ou séparément hydrogène ou un hydrocarbyle, R4 représente hydrogène ou un groupe chimique constitué d'une molécule de liaison L, qui relie un groupe détectable au reste de la structure (I), R5 représente hydrogène ou un groupe électro-attracteur supplémentaire et peut être identique à Z ou différent de celui-ci, R6 représente hydrogène ou un groupe chimique constitué d'une unité de liaison L, d'un groupe clivable et d'un groupe détectable réunis dans l'ordre suivant R6 = -L- groupe clivable-groupe détectable. Le groupe détectable est placé sur R4 ou sur R6 ou est absent et R4 représente alors hydrogène et le groupe détectable est placé sur R6 ou R6 représente hydrogène et le groupe détectable est placé sur R4 ou alors R4 et R6 représentent tous les deux hydrogène. Les nombres m et n représentent indépendamment 0 ou 1. Les composés de formule (I) sont utilisés comme terminateurs d'extension de chaîne réversibles. Cette invention concerne également l'utilisation des composés de formule (I) dans un séquençage d'acides nucléiques, ainsi qu'un procédé de préparation de composés de formule (I).
• [EN] FLUORESCENT RED EMITTING FUNCTIONALIZABLE PH PROBES<br/>[FR] SONDES À PH FONCTIONNALISABLES ÉMETTANT DANS LE ROUGE FLUORESCENT
  申请人：PARIS SCIENCES LETTRES QUARTIER LATIN

  公开号：WO2015097262A1

  公开（公告）日：2015-07-02

  The present invention relates to pH probes of formula I: wherein: W represents O, NH, N(alkyl), Si(alkyl)2, CH2, CH(alkyl), C(alkyl)2; preferably W represents O; X1 and X1' represent both H, both Me or both -CH2-S03H; X2 and X2' represent both H or both Me; X3 and X 3' represent both H or both Me; X4 and X 4' represent both H or both Me; X5 and X5' represent both H or both Me; X6 and X6' represent both H or both Me; Z1, Z2 and Z3, represent each independently H, electron withdrawing group or electron donating group, L represents a single bound or a linker, Y represents a reactive group, or a bioactive group. The invention also relates to a process for manufacturing said compounds. The invention further relates to the use of the compounds of the invention as pH probes.
• Fluorescent Labeling of (Oligo)Nucleotides by a New Fluoride Cleavable Linker Capable of Versatile Attachment Modes
  作者：Diana C. Knapp、Jennifer D’Onofrio、Joachim W. Engels

  DOI：10.1021/bc900542f

  日期：2010.6.16

  The development of a fluoride cleavable linker 1 for reversibly labeling (oligo)nucleotides is described here. The linker allows different ways of chemical attachment of a reporter molecule, for example, click chemistry or amide formation. The versatile attachment modes of labels are demonstrated by derivatizations with pyrene and fluorescein. Besides the synthesis of the new linker, we also show the derivatization of iodobenzene as a model compound and a nucleoside to demonstrate the applicability. Further, cleavability studies in solution and on a solid-supported oligonucleotide are shown. The linker can be applied in the synthesis of reversible terminators, useful for new DNA sequencing technologies like cyclic reversibly terminating (CRT) sequencing.
• Spatiotemporal Investigation of Intercellular Heterogeneity via Multiple Photocaged Probes
  作者：Chun‐Yi Tsai、Po‐Hsun Chen、Ai‐Lin Chen、Tsung‐Shing Andrew Wang

  DOI：10.1002/chem.202301067

  日期：2023.9.15

  Intercellular heterogeneity occurs widely under both normal physiological environments and abnormal disease‐causing conditions. Several attempts to couple spatiotemporal information to cell states in a microenvironment were performed to decipher the cause and effect of heterogeneity. Furthermore, spatiotemporal manipulation can be achieved with the use of photocaged/photoactivatable molecules. Here, we provide a platform to spatiotemporally analyze differential protein expression in neighboring cells by multiple photocaged probes coupled with homemade photomasks. We successfully established intercellular heterogeneity (photoactivable ROS trigger) and mapped the targets (directly ROS‐affected cells) and bystanders (surrounding cells), which were further characterized by total proteomic and cysteinomic analysis. Different protein profiles were shown between bystanders and target cells in both total proteome and cysteinome. Our strategy should expand the toolkit of spatiotemporal mapping for elucidating intercellular heterogeneity.

  摘要 在正常生理环境和异常致病条件下，细胞间异质性广泛存在。为了破译异质性的原因和影响，人们多次尝试将时空信息与微环境中的细胞状态结合起来。此外，利用光笼/可光电激活的分子可以实现时空操纵。在这里，我们提供了一个平台，通过多个光笼式探针和自制光掩膜，对相邻细胞中不同的蛋白质表达进行时空分析。我们成功地建立了细胞间异质性（可光激活的 ROS 触发器），并绘制了目标（直接受 ROS 影响的细胞）和旁观者（周围的细胞）的图谱。在总蛋白组和半胱氨酸组中，旁观者细胞和目标细胞的蛋白质特征各不相同。我们的策略应能扩展时空图谱工具包，用于阐明细胞间的异质性。