(2R)-3-[[(2R,3R,4R,5S,6S)-3-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2R,3R,4S,5R,6S)-6-carbamoyl-3,4,5-trihydroxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-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-(2-oxoethoxy)propanoic acid | 303185-58-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-3-[[(2R,3R,4R,5S,6S)-3-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2R,3R,4S,5R,6S)-6-carbamoyl-3,4,5-trihydroxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-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-(2-oxoethoxy)propanoic acid
• CAS: 303185-58-2
• 化学式: C₄₁H₆₆N₅O₃₃P
• 分子量: 1187.96
• InChiKey: OHQOLLYROPDRBB-XWIKSHJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11.2
• 重原子数：
  80
• 可旋转键数：
  25
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  601
• 氢给体数：
  17
• 氢受体数：
  33

反应信息

• 作为反应物：
  描述：

  (2R)-3-[[(2R,3R,4R,5S,6S)-3-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2R,3R,4S,5R,6S)-6-carbamoyl-3,4,5-trihydroxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-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-(2-oxoethoxy)propanoic acid 在 sodium tetrahydroborate 作用下， 以91%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-5-[(2R,3R,4S,5R,6S)-6-carbamoyl-3,4,5-trihydroxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-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-(2-hydroxyethoxy)propanoic acid
  参考文献：
  名称：

  Some Selective Reactions of Moenomycin A

  摘要：

  A number of new moenomycin A derivatives have been prepared. Their antibiotic properties highlight the very specific recognition of moenomycin A at the transglycosylase binding site which is the basis of the transglycosylase inhibiting property of moenomycin A (4a). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00377-2
• 作为产物：
  描述：

  moenomycin A 在 氧气 、 臭氧 作用下， 以 甲醇 为溶剂， 以98%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-5-[(2R,3R,4S,5R,6S)-6-carbamoyl-3,4,5-trihydroxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-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-(2-oxoethoxy)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

文献信息

• 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)
• Synthesis of tools for raising antibodies against moenomycin epitopes and initial immunological studies
  作者：Andrij Buchynskyy、Katherina Stembera、Dietmar Knoll、Stefan Vogel、Uwe Kempin、Astrid Biallaß (née Donnerstag)、Lothar Hennig、Matthias Findeisen、Dietrich Müller、Peter Welzel

  DOI：10.1016/s0040-4020(02)00838-4

  日期：2002.9

  The moenomycins A and C-1 as well as penta-. di- and monosaccharide analogues have been conjugated to BSA and biotin, respectively, The moenomycin A-BSA conjugates have been used to raise polyclonal antibodies. It has been demonstrated that the antisera recognize moenomycin A. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Moenomycin analogues with long-chain amine lipid parts from reductive aminations
  作者：Stefan Vogel、Katherina Stembera、Lothar Hennig、Matthias Findeisen、Sabine Giesa、Peter Welzel、Claire Tillier、Christian Bonhomme、Maxime Lampilas

  DOI：10.1016/s0040-4020(01)00306-4

  日期：2001.5

  From a moenomycin A glycolic aldehyde degradation product lacking the chromophore unit and most of the lipid part, a number of amines were prepared by reductive amination. Their interaction with artificial membranes as well as their transglycosylase inhibiting and antibiotic properties were studied. (C) 2001 Elsevier Science Ltd. Ah rights reserved.
• Some Selective Reactions of Moenomycin A
  作者：Stefan Vogel、Andrij Buchynskyy、Katka Stembera、Karin Richter、Lothar Hennig、Dietrich Müller、Peter Welzel、Françis Maquin、Christian Bonhomme、Maxime Lampilas

  DOI：10.1016/s0960-894x(00)00377-2

  日期：2000.9

  A number of new moenomycin A derivatives have been prepared. Their antibiotic properties highlight the very specific recognition of moenomycin A at the transglycosylase binding site which is the basis of the transglycosylase inhibiting property of moenomycin A (4a). (C) 2000 Elsevier Science Ltd. All rights reserved.
• Moenomycin analogues with modified lipid side chains from indium-mediated Barbier-type reactions
  作者：Stefan Vogel、Katherina Stembera、Lothar Hennig、Matthias Findeisen、Sabine Giesa、Peter Welzel、Maxime Lampilas

  DOI：10.1016/s0040-4020(01)00301-5

  日期：2001.5

  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.