2-O-<2-acetylamino-4-O-<2-acetylamino-4-O-((5S)-5-carbamoyl-β-L-arabinopyranosyl)-2,6-dideoxy-β-D-glucopyranosyl>-2-deoxy-6-O-β-D-glucopyranosyl-β-D-glucopyranosyl>-3-O-carbamoyl-1-O-<<(S)-2-carboxy-2-((2Z,6E,13E-3,8,8,14,18-pentamethyl-11-methyle.. | 156648-09-8

• 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: 2-O-<2-acetylamino-4-O-<2-acetylamino-4-O-((5S)-5-carbamoyl-β-L-arabinopyranosyl)-2,6-dideoxy-β-D-glucopyranosyl>-2-deoxy-6-O-β-D-glucopyranosyl-β-D-glucopyranosyl>-3-O-carbamoyl-1-O-<<(S)-2-carboxy-2-((2Z,6E,13E-3,8,8,14,18-pentamethyl-11-methyle..
• 英文别名: (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-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]propanoic acid
• CAS: 156648-09-8
• 化学式: C₆₄H₁₀₄N₅O₃₂P
• 分子量: 1486.52
• InChiKey: KUQAHLSJUBYZKY-VIEZKXRXSA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  102
• 可旋转键数：
  37
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  584
• 氢给体数：
  17
• 氢受体数：
  32

反应信息

• 作为反应物：
  描述：

  2-O-<2-acetylamino-4-O-<2-acetylamino-4-O-((5S)-5-carbamoyl-β-L-arabinopyranosyl)-2,6-dideoxy-β-D-glucopyranosyl>-2-deoxy-6-O-β-D-glucopyranosyl-β-D-glucopyranosyl>-3-O-carbamoyl-1-O-<<(S)-2-carboxy-2-((2Z,6E,13E-3,8,8,14,18-pentamethyl-11-methyle.. 在 sodium periodate 、 硫酸 、 sodium acetate 、 溶剂黄146 、 偏二甲肼 作用下， 生成 2-O-<2-acetamido-4-O-<2-acetamido-2,6-dideoxy-β-D-glucopyranosyl>-2-deoxy-β-D-glucopyranosyl>-3-O-carbamoyl-1-O-<<(R)-2-carboxy-2-((2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylene-nonadeca-2,6,13,17-tetraen-1-yloxy)-ethoxy>-hydroxyphosphoryl>-4-...
  参考文献：
  名称：

  A structurally and biogenetically interesting moenomycin antibiotic

  摘要：

  Isolation and structure elucidation of a new moenomycin antibiotic (A(12), 1a) is reported that differs from moenomycin A by lack of the branching methyl group and by the configuration at C-4 of unit F. The smallest antibiotically active degradation product of 1a is the trisaccharide derivative 3a. This observation is in contrast to structure activity relations in the moenomycin A series where it was found that disaccharide 4b is fully active. An explanation is offered for this difference.

  DOI：

  10.1016/0040-4020(94)01074-a
• 作为产物：
  描述：

  moenomycin A 在 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 以58%的产率得到2-O-<2-acetylamino-4-O-<2-acetylamino-4-O-((5S)-5-carbamoyl-β-L-arabinopyranosyl)-2,6-dideoxy-β-D-glucopyranosyl>-2-deoxy-6-O-β-D-glucopyranosyl-β-D-glucopyranosyl>-3-O-carbamoyl-1-O-<<(S)-2-carboxy-2-((2Z,6E,13E-3,8,8,14,18-pentamethyl-11-methyle..
  参考文献：
  名称：

  Moenomycin A: reactions at the lipid part. New structure-activity relations

  摘要：

  Methods for the removal and the oxidation of the lipid moiety of the antibiotic moenomycin A have been studied. Combined with biochemical studies,the results demonstrate that antibiotic activity is closely related with the integrity of the lipid unit.

  DOI：

  10.1016/s0040-4020(01)80688-8

文献信息

• Introduction of a terminal hydroxy group into the lipid part of a moenomycin-type transglycosylase inhibitor suppresses antibiotic activity
  作者：Uwe Kempin、Lothar Hennig、Peter Welzel、Susanne Marzian、Dietrich Müller、Hans-Wolfram Fehlhaber、Astrid Markus、Yveline van Heijenoort、Jean van Heijenoort

  DOI：10.1016/0040-4020(95)00462-h

  日期：1995.7

  On reaction with singlet oxygen 1 provided a mixture of 2 and 3 which could not be separated. In-vivo, 2/3 were antibiotically of low activity whereas in the in-vitro assays at least one of the compounds inhibited the transglycosylase effectively.
• Moenomycin A: reactions at the lipid part. New structure-activity relations
  作者：Susanne Marzian、Markus Happel、Ulrich Wagner、Dietrich Müller、Peter Welzel、Hans-Wolfram Fehlhaber、Andreas Stärk、Hans-Jürgen Schütz、Astrid Markus、Michael Limbert、Yveline van Heijenoort、Jean van Heijenoort

  DOI：10.1016/s0040-4020(01)80688-8

  日期：1994.5

  Methods for the removal and the oxidation of the lipid moiety of the antibiotic moenomycin A have been studied. Combined with biochemical studies,the results demonstrate that antibiotic activity is closely related with the integrity of the lipid unit.
• A structurally and biogenetically interesting moenomycin antibiotic
  作者：Astrid Donnerstag、Susanne Marzian、Dietrich Müller、Peter Welzel、Dirk Böttger、Andreas Stärk、Hans-Wolfram Fehlhaber、Astrid Markus、Yveline van Heijenoort、Jean van Heijenoort

  DOI：10.1016/0040-4020(94)01074-a

  日期：1995.2

  Isolation and structure elucidation of a new moenomycin antibiotic (A(12), 1a) is reported that differs from moenomycin A by lack of the branching methyl group and by the configuration at C-4 of unit F. The smallest antibiotically active degradation product of 1a is the trisaccharide derivative 3a. This observation is in contrast to structure activity relations in the moenomycin A series where it was found that disaccharide 4b is fully active. An explanation is offered for this difference.