acremomannolipin A | 1403981-83-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: acremomannolipin A
• 英文别名: Acremomannolipin A；[(2R,3S,4S,5R,6R)-4,5-di(hexanoyloxy)-6-(hexanoyloxymethyl)-2-[(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexoxy]oxan-3-yl] octanoate
• CAS: 1403981-83-8
• 化学式: C₃₈H₆₈O₁₅
• 分子量: 764.949
• InChiKey: KXOHHVVQXCNKBM-QDOWTLGRSA-N

物化性质

• 沸点：
  818.4±65.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  53
• 可旋转键数：
  34
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  225
• 氢给体数：
  5
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  acremomannolipin A 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 辛酸 、 己酸 、 O¹-β-D-mannopyranosyl-D-mannitol
  参考文献：
  名称：

  Acremomannolipin A, the potential calcium signal modulator with a characteristic glycolipid structure from the filamentous fungus Acremonium strictum

  摘要：

  By the newly developed assay method, the glycolipid Acremomannolipin A (1) was isolated from a filamentous fungus Acremonium strictum as a potential calcium signal modulator. The structure of 1 elucidated on the basis of intensive spectroscopic analyses as well as its degradation studies is quite unique: the D-mannopyranose is connected to D-mannitol through a beta-glycoside linkage; all the hydroxyls in the mannose are highly masked as peresters with aliphatic acids, and this moiety is made hydrophobic, whereas the mannitol part exhibits a highly hydrophilic property. The compound (1) showed the characteristic bioactivity property, enabling calcineurin deletion cells to grow in the presence of Cl-, which would be caused by calcium signal modulating. The activity was so potent as to exert the effect at a concentration of 200 nM. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.085
• 作为产物：
  描述：

  phenyl 2-O-p-methoxybenzyl-3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 palladium 10% on activated carbon 、 氢气 、 间氯过氧苯甲酸 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 23.67h， 生成 acremomannolipin A
  参考文献：
  名称：

  立体选择性全合成acremomannolipin A及其异构体，具有新型糖脂结构的强效钙信号调节剂：在端粒异构中心对活性的立体化学作用

  摘要：

  甲充分考虑的新的糖脂的立体选择性全合成的，acremomannolipin A（1），从分离出的有效的钙信号调制器顶孢strictum，通过采用的4,6-立体选择性β甘露糖基ø -亚苄基保护的甘露糖基砜与d -以甘露醇为关键反应进行了描述。的α端基异构体（EPI - 1）的1，还选择合成。钙调节活性在异头中心在所述构型的反转降低，表明甘露糖部分的β构型是优选的活性。

  DOI：

  10.1016/j.tet.2013.09.086

文献信息

• Glycosyl-Acceptor-Derived Borinic Ester-Promoted Direct and β-Stereoselective Mannosylation with a 1,2-Anhydromannose Donor
  作者：Masamichi Tanaka、Junki Nashida、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1021/acs.orglett.6b00926

  日期：2016.5.6

  in the presence of a glycosyl-acceptor-derived borinic ester. Reactions proceeded smoothly under mild conditions to provide the corresponding β-mannosides with high stereoselectivity in moderate to high yields. In addition, the present glycosylation method was applied successfully to the total synthesis of acremomannolipin A.

  在糖基受体衍生的硼酸酯存在下，使用1,2-脱水甘露糖供体和单醇受体进行β-立体选择性甘露糖基化。反应在温和条件下平稳进行，以中等至高产率提供具有高立体选择性的相应β-甘露糖苷。此外，本糖基化方法已成功地应用于阿莫莫尼脂A的全合成。
• Construction of β-Mannosidic Bonds via Gold(I)-Catalyzed Glycosylations with Mannopyranosyl<i>ortho</i>-Hexynylbenzoates and Its Application in Synthesis of Acremomannolipin A
  作者：Peng Sun、Peng Wang、Yongzhen Zhang、Xiuli Zhang、Cong Wang、Shaojing Liu、Jinjie Lu、Ming Li

  DOI：10.1021/acs.joc.5b00140

  日期：2015.4.17

  A mild and convenient protocol for direct synthesis of beta-mannosides has been developed. Glycosylation of 4,6-O-benzylidene-protected mannosyl ortho-hexynylbenzoates with various alcohol acceptors catalyzed by gold(I) complex proceeded smoothly at 0 degrees C to room temperature and afforded the corresponding beta-mannoside in high yield and satisfactory stereoselectivity. This reaction was applied to the total synthesis of acremomannolipin A and its analogue.
• ANTI-TUMOR AGENT
  申请人：Kinki University

  公开号：EP2716293B1

  公开（公告）日：2017-09-06
• The first total synthesis of acremomannolipin A, the potential Ca2+ signal modulator with a characteristic glycolipid structure, isolated from the filamentous fungus Acremonium strictum
  作者：Nozomi Tsutsui、Genzoh Tanabe、Ayako Kita、Reiko Sugiura、Osamu Muraoka

  DOI：10.1016/j.tetlet.2012.10.128

  日期：2013.2

  The first total synthesis of acremomannolipin A, the potential Ca2+ signal modulator isolated from Acremonium strictum, was achieved by employing the characteristic stereoselective beta-mannosylation of 4,6-O-benzylidene-protected mannosyl sulfoxide with a D-mannitol derivative in the presence of trifluoromethanesulfonic anhydride as the key reaction. (C) 2012 Elsevier Ltd. All rights reserved.
• Acremomannolipin A, the potential calcium signal modulator with a characteristic glycolipid structure from the filamentous fungus Acremonium strictum
  作者：Reiko Sugiura、Ayako Kita、Nozomi Tsutsui、Osamu Muraoka、Kanako Hagihara、Nanae Umeda、Tatsuki Kunoh、Hirofumi Takada、Dai Hirose

  DOI：10.1016/j.bmcl.2012.08.085

  日期：2012.11

  By the newly developed assay method, the glycolipid Acremomannolipin A (1) was isolated from a filamentous fungus Acremonium strictum as a potential calcium signal modulator. The structure of 1 elucidated on the basis of intensive spectroscopic analyses as well as its degradation studies is quite unique: the D-mannopyranose is connected to D-mannitol through a beta-glycoside linkage; all the hydroxyls in the mannose are highly masked as peresters with aliphatic acids, and this moiety is made hydrophobic, whereas the mannitol part exhibits a highly hydrophilic property. The compound (1) showed the characteristic bioactivity property, enabling calcineurin deletion cells to grow in the presence of Cl-, which would be caused by calcium signal modulating. The activity was so potent as to exert the effect at a concentration of 200 nM. (C) 2012 Elsevier Ltd. All rights reserved.