Methyl (R)-2-(3,8,8,11,11,14,18-hexamethylnonadecyloxy-3-hydroxypropionate) | 119771-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl (R)-2-(3,8,8,11,11,14,18-hexamethylnonadecyloxy-3-hydroxypropionate)
• 英文别名: methyl (R)-3-hydroxy-2-(3,8,8,11,14,18-hexamethylnonadecyloxy)-propionate；methyl (R)-2-(3,8,8,11,14,18-hexamethylnonadecyloxy)-3-hydroxypropionate；methyl (2R)-2-(3,8,8,11,14,18-hexamethylnonadecoxy)-3-hydroxypropanoate
• CAS: 119771-93-6
• 化学式: C₂₉H₅₈O₄
• 分子量: 470.777
• InChiKey: CAMORKGPVVXISI-VZWKQKHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  33
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl (R)-2-(3,8,8,11,11,14,18-hexamethylnonadecyloxy-3-hydroxypropionate) 在 铜 、 乙酰丙酮 、 锌 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 2-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3-O-carbamoyl-1-O-{[(R)-2-carboxy-2-(3,8,8,11,14,18-hexamethyl-nonadecyloxy)-ethoxy]-hydroxyphosphoryl}-α-D-glucopyranuronamide
  参考文献：
  名称：

  Moenomycin A: The role of the methyl group in the moenuronamide unit and a general discussion of structure-activity relationships

  摘要：

  Two disaccharide analogues 1b and 17a of moenomycin A have been synthesized and their antibiotic and transglycosylase-inhibiting properties have been determined. The results permit for the first time to arrive at a general view of the structural requirements in this class of compounds necessary to elicit antibiotic activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01063-1
• 作为产物：
  描述：

  moenomycin C₃ 在 盐酸 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 72.0h， 生成 Methyl (R)-2-(3,8,8,11,11,14,18-hexamethylnonadecyloxy-3-hydroxypropionate)
  参考文献：
  名称：

  某些新霉素抗生素的结构-肽聚糖生物合成抑制剂

  摘要：

  描述了新莫能霉素抗生素C 3（1b）和C 4（1c）的分离，结构分配和抗生素效率。修改了先前发表的磷脂霉素（1d）的结构。

  DOI：

  10.1016/s0040-4020(01)89891-4

文献信息

• Synthesis of two structural analogues of the smallest antibiotically active degradation product of moenomycin a
  作者：Heidemarie Hohgardt、Wolfgang Dietrich、Harald Kühne、Dietrich Müller、Detlef Grzelak、Peter Welzel

  DOI：10.1016/s0040-4020(01)81436-8

  日期：1988.1

  The disacchande analogues 19 and 2 of moenomycin A have been synthesized. In contrast to the moenomycin A degradation product 1, synthetic conpounds 19 and 2 do not show antibiotic activity.

  已经合成了莫诺霉素A的令人不快的类似物19和2。与莫那霉素A降解产物1相反，合成化合物19和2没有显示抗生素活性。
• Moenomycin A - Structure-activity relations synthesis of the D-galacturonamide analogue of the smallest antibiotically active degradation product of moenomycin A
  作者：Uwe Möller、Kurt Hobert、Astrid Donnerstrag、Petra Wagner、Dietrich Müller、Hans-Wolfram Fehlhaber、Astrid Markus、Peter Welzel

  DOI：10.1016/s0040-4020(01)80351-3

  日期：——

  Compound 10c which is the galacturonamide analogue of 2, the smallest degradation product of moenomycin A (1) with full antibiotic activity, has been synthesized. 10c is devoid of antibiotic activity.

  合成了化合物10c，它是2的半乳糖醛酰胺类似物，这是具有完全抗生素活性的莫诺霉素A（1）的最小降解产物。10c没有抗生素活性。
• Acceptor site recognition of transglycosylase inhibitors a β-D-glucopyranosyl-(1→2)-α-D-glucopyranuronamide-derived moenomycin analogue
  作者：Falk-Thilo Ferse、Kerstin Floeder、Lothar Hennig、Matthias Findeisen、Peter Welzel、Dietrich Müller、Jean van Heijenoort

  DOI：10.1016/s0040-4020(98)01181-8

  日期：1999.3

  The synthesis, the antibiotic and the transglycosylase inibiting properties of a disaccharide analogue of moenomycin A in which the NHAc group of unit E is replaced by a hydroxyl function are described. It can be concluded that this NHAc group is essential for eliciting transglycosylase inhibiting properties, in agreement with a recently established solution structure of moenomycin A. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A Moenomycin-type Structural Analogue of Lipid II some possible mechanisms of the mode of action of transglycosylase inhibitors can be discarded
  作者：Ralf Kosmol、Lothar Hennig、Peter Welzel、Matthias Findesien、Dietrich Müller、Astrid Markus、Jean van Heijenoort

  DOI：10.1002/prac.19973390162

  日期：——

  The transglycosylation step in the peptidoglycan biosynthesis belongs to the general class of glycosyltransferase-catalyzed reactions. The structural analogue 2 of moenomycin A has been synthesized and has been found to be antibiotically inactive. The assumption that moenomycin-type transglycosylase inhibitors such as 1 bind at the donor site of the enzyme and that their mode of action is the result of the high stability of the sugar --> phosphate bond seems to be ruled out by the present results.
• Synthesis and transglycosylase-inhibiting properties of a disaccharide analogue of moenomycin A lacking substitution at C-4 of unit F
  作者：Sylvia Riedel、Astrid Donnerstag、Lothar Hennig、Peter Welzel、Joachim Richter、Kurt Hobert、Dietrich Müller、Jean van Heijenoort

  DOI：10.1016/s0040-4020(98)01225-3

  日期：1999.2

  A disaccharide analogue (A4 = 13c) of moenomycin A lacking the OH group in the 4-position of the uronic acid moiety has been synthesized using the Saito deoxygenation reaction as key step. 13c does not inhibit the transglycosylase (PBP 1b), a key enzyme in the biosynthesis of bacterial peptidoglycan. The result demonstrates the importance of this OH group for the binding of disaccharide moenomycin analogues to the enzyme. (C) 1999 Elsevier Science Ltd. All rights reserved.