moenomycin A | 76095-39-1

• 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: moenomycin A
• 英文别名: moenomycin；(2R)-3-[[(2R,3R,4R,5S,6S)-3-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-methyl-5-[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-hydroxy-5-oxocyclopenten-1-yl)carbamoyl]oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-carbamoyl-4-carbamoyloxy-5-hydroxy-5-methyloxan-2-yl]oxy-hydroxyphosphoryl]oxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]propanoic acid
• CAS: 76095-39-1
• 化学式: C₆₉H₁₀₈N₅O₃₄P
• 分子量: 1582.6
• InChiKey: CWWXIJNUPCBGQG-HWQYKPDZSA-N

物化性质

• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  109
• 可旋转键数：
  38
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  608
• 氢给体数：
  18
• 氢受体数：
  34

反应信息

• 作为反应物：
  描述：

  moenomycin A 在 sodium periodate 、 sodium acetate 、 溶剂黄146 、 硫酸 、 偏二甲肼 作用下， 以 水 、 异丙醇 为溶剂， 反应 9.5h， 以29%的产率得到(2R)-3-[[(2R,3R,4R,5S,6S)-3-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-carbamoyl-4-carbamoyloxy-5-hydroxy-5-methyloxan-2-yl]oxy-hydroxyphosphoryl]oxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]propanoic acid
  参考文献：
  名称：

  Moenomycin analogues with modified lipid side chains from indium-mediated Barbier-type reactions

  摘要：

  From moenomycin A both the chromophore part and the Lipid side chain were degraded by ozonolysis to give an analogue with a glycolaldehyde unit in 2-position of the glyceric acid moiety. The aldehyde was converted to a number of homoallylic alcohols by indium-mediated Barbier-type reactions with allylic and benzylic halides. With exception of the phytyl bromide-derived reaction product all compounds were antibiotically inactive. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00301-5
• 作为产物：
  描述：

  N1-[(2-hydroxy-5-oxo-cyclopenten-1-yl)-2,3,4-tri-O-acetyl-(5S)-β-D-galactopyranuronamide]-(1-4)-2-acetamide-3-O-acetyl-2,6-dideoxy-β-D-glucopyranosyl-(1-4)-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1-6)-2-acetamido-3-O-acetyl-2-deoxy-β-D-glucopyranosyl]-(1-2)-3-O-carbamoyl-1H-{[(R)-2-methoxycarbonyl-2-((2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylene-nonadeca-2,6,13,17-tetraen-1-yloxy)-ethoxy]-hydroxyphosphoryl}-4-C-methyl-α-D-glucopyranuronamide ammonium salt 在 lithium hydroxide 、 乙酸酐 作用下， 以 四氢呋喃 、 水 为溶剂， 以47%的产率得到moenomycin A
  参考文献：
  名称：

  莫诺霉素A的全合成

  摘要：

  Moenomycin A 是唯一一种已知的天然抗生素，它通过与催化肽聚糖碳水化合物链形成的转糖基酶结合来抑制细菌细胞壁合成。我们在这里报告了使用亚砜糖基化方法对 moenomycin A 的全合成。分离出一种新发现的亚砜反应副产物，该副产物导致糖基受体的大量损失。介绍了一种抑制这种副产物的通用方法，它使糖基化能够有效地进行。亚砜糖基化的反向添加协议也证明在构建一些糖苷键时必不可少。合成路线灵活，可以构建衍生物以进一步分析莫诺霉素 A 的作用机制。

  DOI：

  10.1021/ja065907x

文献信息

• A Method for the Introduction of Reporter Groups into Moenomycin A, Based on Thiouronium Salt Chemistry
  作者：Andrij Buchynskyy、Katherina Stembera、Lothar Hennig、Matthias Findeisen、Sabine Giesa、Peter Welzel

  DOI：10.1002/1099-0690(200204)2002:7<1163::aid-ejoc1163>3.0.co;2-c

  日期：2002.4

  21b reacted selectively with the 2-acylamino-1,3-cyclopentanedione unit A of moenomycin A (1) to give the corresponding 2-alkylated products 14a, 14b, 22a, and 22b. These products, depending on the pH of the solution, were either stable under the reaction conditions or they underwent retro-Claisen-type reactions. The method can be used for the attachment of reporter groups to moenomycin A for the synthesis

  对烷氧基取代的肉桂基硫脲盐 7、13、21a 和 21b 与莫诺霉素 A (1) 的 2-酰氨基-1,3-环戊二酮单元 A 选择性反应，得到相应的 2-烷基化产物 14a、14b、22a，和 22b。这些产物，取决于溶液的 pH 值，要么在反应条件下稳定，要么经历逆克莱森型反应。该方法可用于将报告基团连接到 moenomycin A 以合成例如 25。 (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• [EN] INHIBITORS OF BACTERIAL GLYCOSYL TRANSFERASES<br/>[FR] INHIBITEURS DE GLYCOSYL TRANSFÉRASES BACTÉRIENNES
  申请人：HARVARD COLLEGE

  公开号：WO2016191658A1

  公开（公告）日：2016-12-01

  Described herein are compounds of Formula (I'), Formula (IA), Formulae (I)-(VII), pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, and prodrug sthereof. The invention also provides pharmaceutical compositions of the compounds for human and veterinary use. Compounds of the present invention are useful for inhibiting bacterial growth and therefore are useful in treating and/or preventing bacterial infections. Methods of using the compounds for treating and/or preventing a bacterial infection in a subject are also described.

  本文描述了式(I')、式(IA)、式(I)-(VII)的化合物，以及这些化合物的药用盐、溶剂合物、水合物、多型体、共晶体、互变异构体、立体异构体、同位素标记衍生物和前药。本发明还提供了这些化合物的用于人类和兽医用途的药物组合物。本发明的化合物对抑制细菌生长有用，因此在治疗和/或预防细菌感染方面具有用途。还描述了使用这些化合物治疗和/或预防受试者细菌感染的方法。
• [EN] SUBSTITUTED HETEROARYL- AND PHENYLSULFAMOYL COMPOUNDS<br/>[FR] COMPOSES HETEROARYLE ET PHENYLSULFAMOYLE SUBSTITUES
  申请人：PFIZER PROD INC

  公开号：WO2005092845A1

  公开（公告）日：2005-10-06

  The present invention is directed at substituted heteroaryl- and phenylsulfamoyl compounds, pharmaceutical compositions containing such compounds and the use of such compounds as peroxisome proliferator activator receptor (PPAR) agonists. PPAR alpha activators, pharmaceutical compositions containing such compounds and the use of such compounds to elevate certain plasma lipid levels, including high density lipoprotein-cholesterol and to lower certain other plasma lipid levels, such as LDL-cholesterol and triglycerides and accordingly to treat diseases which are exacerbated by low levels of HDL cholesterol and/or high levels of LDL-cholesterol and triglycerides, such as atherosclerosis and cardiovascular diseases, in mammals, including humans. The compounds are also useful for the treatment of negative energy balance (NEB) and associated diseases in ruminants.

  本发明涉及取代杂环芳基和苯基磺酰胺化合物，含有这种化合物的药物组合物以及将这种化合物用作过氧化物酶增殖激活受体（PPAR）激动剂的用途。PPARα激活剂，含有这种化合物的药物组合物以及使用这种化合物提高特定血浆脂质水平，包括高密度脂蛋白胆固醇，并降低其他特定血浆脂质水平，如低密度脂蛋白胆固醇和甘油三酯，从而治疗由高密度脂蛋白胆固醇水平低和/或低密度脂蛋白胆固醇和甘油三酯水平高加重的疾病，如动脉粥样硬化和心血管疾病，在哺乳动物，包括人类中。这些化合物还可用于治疗反常能量平衡（NEB）和反常相关疾病的反刍动物。
• Synthesis of Fluorescent Derivatives of the Antibiotic Moenomycin A
  作者：Andrij Buchynskyy、Uwe Kempin、Stefan Vogel、Lothar Hennig、Matthias Findeisen、Dietrich Müller、Sabine Giesa、Helmut Knoll、Peter Welzel

  DOI：10.1002/1099-0690(200204)2002:7<1149::aid-ejoc1149>3.0.co;2-h

  日期：2002.4

  Moenomycin has been highly selectively converted into amino derivative 3b. The primary amino group of this compound can be used to attach various fluorescent labels to moenomycin, through conversion of isothiocyanates into thioureas and squaric acid diesters into diamides. The application of some of the derivatives is outlined. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  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)
• [EN] METHODS AND COMPOUNDS FOR IDENTIFYING GLYCOSYLTRANSFERASE INHIBITORS<br/>[FR] PROCÉDÉS ET COMPOSÉS POUR L'IDENTIFICATION D'INHIBITEURS DE GLYCOSYLTRANSFÉRASE
  申请人：HARVARD COLLEGE

  公开号：WO2013151697A1

  公开（公告）日：2013-10-10

  The present invention provides moenomycin-based probe compounds of Formula (I) for use in screening inhibitors of bacterial glycosyltransferases. The present invention also provides bacterial glycosyltransferase screening assays using compounds of Formula (I).

  本发明提供了用于筛选细菌糖基转移酶抑制剂的以莫诺霉素为基础的探针化合物的公式(I)。本发明还提供了使用公式(I)化合物进行细菌糖基转移酶筛选的检测方法。