1,2,3,4,6-penta-O-chloroacetyl-α,β-D-glucopyranose | 830322-96-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,4,6-penta-O-chloroacetyl-α,β-D-glucopyranose
• 英文别名: 1,2,3,4,6-penta-O-chloroacetylglucose；1,2,3,4,6-penta(chloroacetyl)glucose；1,2,3,4,6-pentachloroacetylglucose
• CAS: 830322-96-8
• 化学式: C₁₆H₁₇Cl₅O₁₁
• 分子量: 562.569
• InChiKey: AMPORDCCVYGWRN-QEJDANBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1,2,3,4,6-penta-O-chloroacetyl-α,β-D-glucopyranose 在 氢溴酸 、 溶剂黄146 作用下， 生成 2,3,4,6-Tetra-O-chloroacetyl-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  GLYCOSYLATED VALPROIC ACID ANALOGS AND USES THEREOF

  摘要：

  提供了糖基化的丙戊酸及其类似物。在某些实施方式中，糖基化的丙戊酸及其类似物具有改善的溶解性，并且非常适合用于药物输送以治疗各种疾病。

  公开号：

  US20130029924A1
• 作为产物：
  描述：

  可得然胶 、 氯乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 以98%的产率得到1,2,3,4,6-penta-O-chloroacetyl-α,β-D-glucopyranose
  参考文献：
  名称：

  [EN] GLUCOSYL ESTERS FOR INFECTION SCREENING
  [FR] ESTERS DE GLUCOSYLE POUR LE DÉPISTAGE D'UNE INFECTION

  摘要：

  揭示了用于检测和/或测量样品中LE活性的葡萄糖酰基酯或其盐或溶剂的组合物和使用方法。

  公开号：

  WO2021242945A1

文献信息

• Functional synthetic molecules and macromolecules for gene delivery
  申请人：Grinstaff W. Mark

  公开号：US20060241071A1

  公开（公告）日：2006-10-26

  The present invention describes a synthetic non-viral vector composition for gene therapy and the use of such compositions for in vitro, ex vivo and/or in vivo transfer of genetic material. The invention proposes a pharmaceutical composition containing 1) a non-cationic amphiphilic molecule or macromolecule and its use for delivery of nucleic acids or 2) a cationic amphiphilic molecule or macromolecule that transforms from a cationic entity to an anionic, neutral, or zwitterionic entity by a chemical, photochemical, or biological reaction and its use for delivery of nucleic acids. Moreover this invention describes the use of these non-viral vector compositions in conjunction with a surface to mediate the delivery of nucleic acids. An additional embodiment is the formation of a hydrogel with these compositions and the use of this hydrogel for the delivery of genetic material. A further embodiment of this invention is the use of a change in ionic strength for the delivery of genetic material.

  本发明描述了一种用于基因治疗的合成非病毒载体组合，以及这种组合在体外、体内和/或体外转移遗传物质中的应用。该发明提出了一种包含1）非阳离子性两性分子或大分子的药物组合物及其用于传递核酸或2）由化学、光化学或生物反应从阳离子实体转变为阴离子、中性或带电离子实体的两性阳离子分子或大分子的药物组合物，以及其用于核酸传递。此外，本发明描述了这些非病毒载体组合物与表面结合以介导核酸传递的应用。另一实施例是使用这些组合物形成水凝胶，并利用该水凝胶传递遗传物质。本发明的另一实施例是利用离子强度变化传递遗传物质。
• Infection Screening in Biofluids with Glucose Test Strips
  作者：Michael Bekhit、Hua-Yu Wang、Stanton McHardy、Waldemar Gorski

  DOI：10.1021/acs.analchem.9b05313

  日期：2020.3.3

  The four glucosyl esters were synthesized and tested for the determination of infection enzyme leukocyte esterase (LE) in human synovial (joint) fluid and urine. The esters acted as LE substrates releasing glucose in a direct proportion to the activity of LE in a sample. The freed glucose was then detected by a coupled-enzyme assay at either a nitrogen-doped carbon nanotube (N-CNT) electrode or a commercial glucose test strip. The assays at the N-CNT electrode detected LE down to 0.81 nM (25 μg L–1) and showed the fastest kinetics (2.1 × 105 M–1 s–1) for esters with the least crowded space around their carbonyl group. When used with glucose strips, the esters discerned clinically relevant levels of LE up to at least 26 nM (800 μg L–1) in the microliter-sized samples of bodily fluids. The reading of glucose strips with a potentiostat, instead of a personal glucose meter (blood glucometer), shortened the time of required sample incubation from 3 h to 5 min. Correcting the signal of incubated sample for that of original sample eliminated matrix effects and accounted for the presence of native glucose. The new esters have a potential to extend the use of glucose strips (already used by millions for diabetes monitoring) to the quantification of the severity of urinary tract and periprosthetic joint infections.

  这四种葡萄糖苷酯被合成并用于检测人类滑膜（关节）液和尿液中感染酶白细胞酯酶（LE）。这些酯作为LE的底物，释放的葡萄糖与样本中LE的活性成正比。然后，通过在氮掺杂碳纳米管（N-CNT）电极或商业葡萄糖测试条上的耦合酶测定法检测释放的葡萄糖。在N-CNT电极上的测定可以检测到0.81 nM（25 μg L–1）的LE，并且对于碳酰基周围空间最少的酯，显示了最快的动力学（2.1 × 10^5 M–1 s–1）。当与葡萄糖测试条一起使用时，这些酯可以在微升体液样本中识别出至少达到临床相关水平的LE，值高达26 nM（800 μg L–1）。使用电位计读取葡萄糖测试条，而不是个人葡萄糖仪（血糖仪），将所需的样本培养时间从3小时缩短到5分钟。对培养样本的信号进行纠正以反映原始样本的信号，消除了基质效应，并考虑了内源性葡萄糖的存在。这些新的酯有潜力将葡萄糖测试条（已为数百万糖尿病监测者使用）扩展到尿路和关节假体周围感染严重程度的量化。
• Hydroxycinnamoyl Glucose and Tartrate Esters and Their Role in the Formation of Ethylphenols in Wine
  作者：Josh L. Hixson、Yoji Hayasaka、Christopher D. Curtin、Mark A. Sefton、Dennis K. Taylor

  DOI：10.1021/acs.jafc.6b04074

  日期：2016.12.14

  hydroxycinnamoyl glucose esters during preparation were investigated to prevent these in subsequent synthetic attempts. Photoisomerization gave an isomeric mixture containing the trans-esters and undesired cis-esters, and acyl migration resulted in a mixture of the desired 1-O-β-ester and two additional migrated forms, the 2-O-α- and 6-O-α-esters. Theoretical studies indicated that the photoisomerization was facilitated

  合成p -coumaroyl和阿魏升-酒石酸盐酯已提交酒香bruxellensis株AWRI 1499，1608 AWRI和AWRI 1613，以评估它们作为前体在酒乙基苯酚作用。没有观察到乙酚的放出。另外，合成了对-香豆酰基葡萄糖和阿魏酰基葡萄糖，并提交给B. bruxellensis AWRI 1499，其产生4-乙基苯酚和4-乙基愈创木酚。研究了在制备过程中羟基肉桂酰基葡萄糖酯的意外化学转化，以防止在随后的合成尝试中发生这些化学转化。光异构化得到含有反式酯和不希望的顺式的异构体混合物-酯，和酰基转移导致所需的1-的混合物ö和两个附加迁移形式-β-酯，2- Ò -α-和6- ö -α-酯。理论研究表明，苯酚的去质子化促进了光异构化，并且在酸性，非水处理过程中有利于酰基迁移。初步的LC-MS / MS研究观察到葡萄酒中迁移的羟基肉桂酰葡萄糖酯，首次允许鉴定红酒中的阿魏酰葡萄糖。
• Synthesis of aryl d-gluco- and d-galacto-pyranosides and 1-O-acyl-d-gluco- and -d-gluco-pyranoses exploiting the mitsunobu reaction. Influence of the pKa of the acid on the stereoselectivity of the reaction
  作者：André Lubineau、Elsa Meyer、Pierre Place

  DOI：10.1016/s0008-6215(00)90559-7

  日期：1992.4

  Glycosides (alpha- and beta-D-glucosides and -D-galactosides) derived from three pesticides, 2-tert-butyl-2,4-dinitrophenol,2,6-dibromo-4-cyanophenol, and 5-(2,4-dichlorophenoxy)-2-nitrobenzoic acid, were synthesized from 2,3,4,6-tetra-O-chloroacetyl-D-gluco- and -D-galactopyranose by use of the Mitsunobu reaction. It was shown that selectivity for the beta-D anomer increases with the pK(a) of the acid component.
• Stereoselective synthesis of 1-O-β-feruloyl and 1-O-β-sinapoyl glucopyranoses
  作者：Yimin Zhu、John Ralph

  DOI：10.1016/j.tetlet.2011.05.038

  日期：2011.7

  1-O-beta-Feruloyl and 1-O-beta-sinapoyl glucopyranoses are two common substrates for serine carboxypeptidase-like acyltransferases and serve as acyl donors in the biosynthesis of numerous secondary metabolites. In addition, they are involved in plant cell wall cross-linking and are also ideal substrates for studying the kinetics of lignification involving hydroxycinnamates. We report the first chemical (and multi-gram scale) synthesis of 1-O-beta-feruloyl and 1-O-beta-sinapoyl glucopyranoses. (C) 2011 Elsevier Ltd. All rights reserved.