4-[5-[(2R,3R,4S,5R,6S)-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3R,4R,5S,6S)-6-carbamoyl-4-carbamoyloxy-2-[[(2R)-2-carboxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]ethoxy]-hydroxy-oxidophosphaniumyl]oxy-5-hydroxy-5-methyloxan-3-yl]oxy-4-hydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]-1-[3-(2-aminoethylcarbamoyl)-4-nitrophenyl]-1,2,4-triazol-3-yl]-4-oxobutanoic acid | 261640-46-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-[5-[(2R,3R,4S,5R,6S)-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3R,4R,5S,6S)-6-carbamoyl-4-carbamoyloxy-2-[[(2R)-2-carboxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]ethoxy]-hydroxy-oxidophosphaniumyl]oxy-5-hydroxy-5-methyloxan-3-yl]oxy-4-hydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]-1-[3-(2-aminoethylcarbamoyl)-4-nitrophenyl]-1,2,4-triazol-3-yl]-4-oxobutanoic acid
• CAS: 261640-46-4
• 化学式: C₇₈H₁₁₇N₁₀O₃₇P
• 分子量: 1817.81
• InChiKey: ZVXWAGYTLZONMD-GIRRWVEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  126
• 可旋转键数：
  45
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  733
• 氢给体数：
  19
• 氢受体数：
  40

反应信息

• 作为反应物：
  描述：

  Fluorescein isothiocyanate 、 4-[5-[(2R,3R,4S,5R,6S)-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3R,4R,5S,6S)-6-carbamoyl-4-carbamoyloxy-2-[[(2R)-2-carboxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]ethoxy]-hydroxy-oxidophosphaniumyl]oxy-5-hydroxy-5-methyloxan-3-yl]oxy-4-hydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]-1-[3-(2-aminoethylcarbamoyl)-4-nitrophenyl]-1,2,4-triazol-3-yl]-4-oxobutanoic acid 生成
  参考文献：
  名称：

  抗生素莫恩霉素A荧光衍生物的合成

  摘要：

  Moenomycin 已被高度选择性地转化为氨基衍生物 3b。通过将异硫氰酸酯转化为硫脲，将方酸二酯转化为二酰胺，该化合物的伯氨基可用于将各种荧光标记物连接到莫诺霉素上。概述了一些衍生物的应用。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  DOI：

  10.1002/1099-0690(200204)2002:7<1149::aid-ejoc1149>3.0.co;2-h
• 作为产物：
  描述：

  moenomycin A 、 5-amino-N-(2-aminoethyl)-2-nitrobenzamide 在 sodium nitrite 作用下， 以38%的产率得到4-[5-[(2R,3R,4S,5R,6S)-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3R,4R,5S,6S)-6-carbamoyl-4-carbamoyloxy-2-[[(2R)-2-carboxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]ethoxy]-hydroxy-oxidophosphaniumyl]oxy-5-hydroxy-5-methyloxan-3-yl]oxy-4-hydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]-1-[3-(2-aminoethylcarbamoyl)-4-nitrophenyl]-1,2,4-triazol-3-yl]-4-oxobutanoic acid
  参考文献：
  名称：

  Membrane Anchoring and Intervesicle Transfer of a Derivative of the Antibiotic Moenomycin A

  摘要：

  The anchoring of moenomycin A (1) to the bacterial cell cytoplasmic membrane is essential for its biological activity. The first details of the strength of this interaction and the kinetics of the diffusion-mediated intervesicle transfer have been obtained by means of fluorescence spectroscopic methods using a coumarin-labeled moenomycin A derivative.

  DOI：

  10.1002/(sici)1521-3773(19991216)38:24<3703::aid-anie3703>3.0.co;2-1

文献信息

• Studies on the interaction of the antibiotic moenomycin A with the enzyme penicillin-binding protein 1b
  作者：Thomas Rühl、Mohammed Daghish、Andrij Buchynskyy、Karen Barche、Daniela Volke、Katherina Stembera、Uwe Kempin、Dietmar Knoll、Lothar Hennig、Matthias Findeisen、Ramona Oehme、Sabine Giesa、Juan Ayala、Peter Welzel

  DOI：10.1016/s0968-0896(03)00187-1

  日期：2003.7

  enzyme penicillin binding protein 1b (PBP 1b) has been studied by means of STD NMR. The results obtained initiated the synthesis of a number of moenomycin derivatives modified in unit A including a moenomycin-ampicillin conjugate and determination of their antibiotic activities. A protocol is described that allows studying the interaction of moenomycin analogues with PBP 1b by fluorescence correlation

  已经通过STD NMR研究了莫诺霉素衍生物与酶青霉素结合蛋白1b（PBP 1b）的相互作用。获得的结果启动了许多在A单元中修饰的莫诺霉素衍生物的合成，包括莫诺霉素-氨苄青霉素结合物及其抗生素活性的测定。描述了一种协议，该协议允许通过荧光相关光谱研究莫能霉素类似物与PBP 1b的相互作用。
• Harnessing Fluorescent Moenomycin A Antibiotics for Bacterial Cell Wall Imaging Studies
  作者：Pei‐Yu Hsieh、Fan‐Chun Meng、Chih‐Wei Guo、Kung‐Hsiang Hu、Yu‐Ling Shih、Wei‐Chieh Cheng

  DOI：10.1002/cbic.202100433

  日期：2021.12.10

  Moenomycin A (MoeA)-based fluorescent probes were developed for imaging the bacterial cell wall through specific labeling of transglycosylases. The strategy provided stunning imaging probes for mecA-carrying methicillin-resistant Staphylococcus aureus (MRSA) strains.

  开发了基于Moenomycin A (MoeA)的荧光探针，用于通过转糖基酶的特异性标记对细菌细胞壁进行成像。该策略为携带mecA的耐甲氧西林金黄色葡萄球菌(MRSA) 菌株提供了惊人的成像探针。
• Tetrafunctional Photoaffinity Labels Based on Nakanishi'sm-Nitroalkoxy-Substituted Phenyltrifluoromethyldiazirine
  作者：Mohammed Daghish、Lothar Hennig、Matthias Findeisen、Sabine Giesa、Frank Schumer、Horst Hennig、Annette G. Beck-Sickinger、Peter Welzel

  DOI：10.1002/1521-3773(20020703)41:13<2293::aid-anie2293>3.0.co;2-9

  日期：2002.7.3
• Synthesis of Neo-Peptidoglycans: An Unexpected Activity of Proteases
  作者：Nicole Wehofsky、Reik Löser、Andrij Buchynskyy、Peter Welzel、Frank Bordusa

  DOI：10.1002/1521-3773(20020802)41:15<2735::aid-anie2735>3.0.co;2-e

  日期：2002.8.2
• Ruehl, Thomas; Volke, Daniela; Stembera, Katherina, Chemical Communications, 2002, # 15, p. 1630 - 1631
  作者：Ruehl, Thomas、Volke, Daniela、Stembera, Katherina、Hatanaka, Yasumaru、Hennig, Horst、Schumer, Frank、Welzel, Peter

  DOI：——

  日期：——