vancomycin hydrocholoride

• 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: vancomycin hydrocholoride
• 英文别名: Vancomycin hydrochloride；vancomycin；Vancocine；(1S,2R,18R,19R,22S,25R,28R,40R)-48-[(2S,3R,4S,5S,6R)-3-[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[[(2R)-4-methyl-2-(methylazaniumyl)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylate;hydrochloride
• 化学式: C₆₆H₇₅Cl₂N₉O₂₄*ClH
• 分子量: 1485.73
• InChiKey: LCTORFDMHNKUSG-PBHRHZHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.83
• 重原子数：
  102
• 可旋转键数：
  12
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  538
• 氢给体数：
  19
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  反-1-辛烯-1-基硼酸 、 vancomycin hydrocholoride 在 sSPhos 、 sodium acetate 、 palladium diacetate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 以25%的产率得到10-dechloro-10-(trans-oct-1-en-1-yl)-vancomycin
  参考文献：
  名称：

  发现了新型的抗万古霉素细菌的半合成万古霉素衍生物系列

  摘要：

  制备了具有抗万古霉素金黄色葡萄球菌（VRSA）抗菌活性的新型半合成万古霉素衍生物。首次描述了通过铃木-宫浦交叉偶联反应置换万古霉素的Cl基团，得到标题化合物。在万古霉素的氨基酸残基2处引入碳取代基导致对耐万古霉素菌株的抗菌活性增强，而在氨基酸残基6处的额外引入甚至导致对万古霉素敏感菌株的活性降低。

  DOI：

  10.1021/jm9017543

文献信息

• Interfacial self-assembly leads to formation of fluorescent nanoparticles for simultaneous bacterial detection and inhibition
  作者：Chunhua Ren、Huaimin Wang、Xiaoli Zhang、Dan Ding、Ling Wang、Zhimou Yang

  DOI：10.1039/c3cc48807a

  日期：——

  Interfacial self-assembly of a NBD–vancomycin conjugate was applied for bacterial detection and inhibition simultaneously.

  利用NBD-万古霉素共轭物的界面自组装技术，同时实现了细菌检测和抑制。
• Tuning the Polarity of Antibiotic‐Cy5 Conjugates Enables Highly Selective Labeling of Binding Sites
  作者：Fabian Graßl、Maike M. B. Konrad、Jasmin Krüll、Azra Pezerovic、Leon Zähnle、Andreas Burkovski、Markus R. Heinrich

  DOI：10.1002/chem.202301208

  日期：2023.8.10

  Multidrug‐resistant bacteria pose a major threat to global health, even as newly introduced antibiotics continue to lose their therapeutic value. Against this background, deeper insights into bacterial interaction with antibiotic drugs are urgently required, whereas fluorescently labeled drug conjugates can serve as highly valuable tools. Herein, the preparation and biological evaluation of 13 new fluorescent antibiotic‐Cy5 dye conjugates is described, in which the tuning of the polarity of the Cy5 dye proved to be a key element to achieve highly favorable properties for various fields of application.

  摘要多重耐药细菌对全球健康构成重大威胁，即使新引进的抗生素也在不断失去治疗价值。在此背景下，迫切需要深入了解细菌与抗生素药物之间的相互作用，而荧光标记的药物共轭物可以作为非常有价值的工具。本文介绍了 13 种新型荧光抗生素-Cy5 染料共轭物的制备和生物学评价，其中 Cy5 染料极性的调整被证明是实现各种应用领域中非常有利特性的关键因素。
• Synthesis of covalent head-to-tail dimers of vancomycin
  作者：Thomas Staroske、Dudley H. Williams

  DOI：10.1016/s0040-4039(98)00895-8

  日期：1998.7

  The synthesis of covalent dimers of vancomycin which are linked from C-to N-terminus (head-to-tail linkage) is described. Such dimers have the potential to exploit additional cooperative interactions when binding to bacterial cell-wall precursors at a surface. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Total Synthesis of Isokidamycin
  作者：B. Michael O’Keefe、Douglas M. Mans、David E. Kaelin、Stephen F. Martin

  DOI：10.1021/ja107926f

  日期：2010.11.10

  The synthesis of isokidamycin, which represents the first total synthesis of a bis-C-aryl glycoside natural product in the pluramycin family, has been completed. The synthesis features the use of a silicon tether as a disposable regiocontrol element in an intramolecular Diels-Alder reaction between a substituted naphthyne and a glycosyl furan and a subsequent O -> C-glycoside rearrangement.
• Porphyrin-vancomycin: A highly promising conjugate for the identification and photodynamic inactivation of antibiotic resistant Gram-positive pathogens
  作者：Le Zhai、Ke-Wu Yang

  DOI：10.1016/j.dyepig.2015.04.017

  日期：2015.9

  The emergence of drug-resistant pathogens is a global public health problem. With the increasing antibiotic resistance of bacteria, there is an obvious need for the development for alternative therapeutics and materials that can effectively control this situation. In this work, a new conjugate, 5,10,15,20-tetrakis (para-aminophenyl) porphyrin-vancomycin was successfully explored for the identification and photoinactivation of antibiotic resistant Gram-positive pathogens. The minimum inhibitory concentration assay and photodynamic inactivation evaluation results revealed that the conjugate can effective inhibit the growth of 6 tested pathogenic strains under white light. The interaction intensity of the conjugate with Gram-positive and Gram-negative bacterial cells was evaluated by surface plasmon resonance, and the results showed that its activity toward Staphylococcus aureus was 14-fold larger than its activity toward Escherichia coli at 20 mM, indicating the conjugate selectively gathers in Gram-positive cells. (C) 2015 Elsevier Ltd. All rights reserved.