n-hexadecanyl α-D-galactopyranoside | 103000-88-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: n-hexadecanyl α-D-galactopyranoside
• 英文别名: hexadecyl β-D-galactopyranoside；Cetyl-β-galactoside；hexadecyl-β-D-galactopyranoside；(2R)-2r-Hexadecyloxy-6c-hydroxymethyl-tetrahydro-pyran-3t,4c,5c-triol；Hexadecyl-β-D-galactopyranosid；(2R,3R,4S,5R,6R)-2-hexadecoxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 103000-88-0；75319-63-0；123000-26-0；142696-64-8；146453-38-5
• 化学式: C₂₂H₄₄O₆
• 分子量: 404.588
• InChiKey: PAEMERHSTIDLSE-CDJZJNNCSA-N

物化性质

• 熔点：
  145 °C
• 沸点：
  543.6±50.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  n-hexadecanyl α-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 Lipase PS 、 三氟甲磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 52.0h， 生成 hexadecyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-6-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Ganglioside Gm4 Analogs as Potential Immunosuppressive Agents

  摘要：

  An efficient, chemoenzymatic synthesis of ganglioside GM4 analogs having a potent immunosuppressive activity is described. One-step and highly regioselective 6-O-acetylation of long-chain alkyl, 2-(trimethysilyl)ethyl and phenyl 1-thio beta-D-galactopyranosides was performed by using vinyl acetate and lipase PS. The resulting 6-O-acetates (70-93%) were sialylated with methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate promoted by N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH). The 2-(trimethylsilyl)ethyl glycoside derivative was converted to the imidate which was then coupled with dodecan-1-ol, hexadecan-1-ol, and 2-(tetradecyl)hexadecan-1-ol, respectively, to give the protected GM4 derivatives (90-96%). O-Deacylation and saponification of the methyl ester gave the target ganglioside GM4 analogs in high yields.

  DOI：

  10.1080/07328309908543992
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 甲醇 、 氢溴酸 、 sodium methylate 、 溶剂黄146 、 silver(l) oxide 作用下， 以 氯仿 为溶剂， 生成 n-hexadecanyl α-D-galactopyranoside
  参考文献：
  名称：

  赋予凝集素诱导的脂质体凝集能力的半乳糖衍生物的合成。

  摘要：

  三种半乳糖（Gal）衍生物，Gal beta 1-n-C16H33（1），Gal beta（1-4）-Glc beta 1-n-C16H33（2）和Gal beta 1-（CH2CH2O）3-n-C16H33 （3）被合成并掺入由蛋黄卵磷脂制备的脂质体中。通过追踪浊度的变化来检查这些脂质体与蓖麻蓖麻凝集素的凝集。与1和2的情况相比，含有3的脂质体被有效凝集，表明氧乙烯基团是将Gal基团挤出到水中的有利间隔基。差示扫描量热法显示3在室温下与蛋黄卵磷脂混合，而1和2处于凝胶状态，导致相分离，这使得Ricinus communis凝集素难以识别Gal残基。

  DOI：

  10.1002/jps.2600820311

文献信息

• Antimicrobial and cytotoxic activity of (thio)alkyl hexopyranosides, nonionic glycolipid mimetics
  作者：Petr Džubák、Soňa Gurská、Kateřina Bogdanová、Daniela Uhríková、Nina Kanjaková、Sophie Combet、Tomáš Klunda、Milan Kolář、Marian Hajdúch、Monika Poláková

  DOI：10.1016/j.carres.2019.107905

  日期：2020.2

  as well as for antimicrobial potential on 12 bacterial and yeast strains. The most potent compounds were found to be tetradecyl and hexadecyl β-d-galactopyranosides (18, 19), which showed the best cytotoxicity and therapeutic index against CCRF-CEM cancer cell line. Similar cytotoxic activity showed hexadecyl α-d-mannopyranoside (5) but it also inhibited non-tumor cell lines. Because these two galactosides

  研究了一系列衍生自d-甘露糖，d-葡萄糖和d-半乳糖的，具有C10-C16糖苷配基的19种合成烷基和硫代烷基糖苷对7种人类癌症和2种非肿瘤细胞系的细胞毒活性以及抗菌潜力在12种细菌和酵母菌株上。发现最有效的化合物是十四烷基和十六烷基β-d-吡喃半乳糖苷（18、19），显示出对CCRF-CEM癌细胞系最佳的细胞毒性和治疗指数。相似的细胞毒活性显示十六烷基α-d-甘露吡喃糖苷（5），但它也抑制了非肿瘤细胞系。因为这两个半乳糖苷（18、19）对所有测试的细菌和酵母菌株均无活性，所以它们可能是真核细胞的靶标特异性靶标。另一方面，具有十四烷基（11）和十六烷基（12）糖苷配基的β-D-吡喃葡萄糖苷仅抑制革兰氏阳性菌粪肠球菌。从POPC模型膜上的SAXS实验推导，所研究的苷在高浓度下诱导脂质双层厚度和侧向相分离的变化。通常，葡糖苷和半乳糖苷表现出更具体的性质。具有较长糖苷配基的化合物显示出高细胞毒性，
• The anomeric mixture of some O-galactolipid derivatives is more toxic against cancer cells than either anomer alone
  作者：Shao-Xing Song、Ming-Li Wu、Xiao-Peng He、Yu-Bo Zhou、Li Sheng、Jia Li、Guo-Rong Chen

  DOI：10.1016/j.bmcl.2012.01.069

  日期：2012.3

  The anomeric mixture of a series of O-galactolipid derivatives is revealed to be more toxic against several cancer cell lines than their either single component with the pure alpha- or beta-configuration. This interesting phenomenon has been confirmed on pairs of synthesized O-galactosyl anomers bearing length-varied alkyl chains at the lipid end. Furthermore, the most potent mixture was determined inoffensive to a normal cell line tested. (C) 2012 Elsevier Ltd. All rights reserved.
• Hori; Ikegami, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 80,82
  作者：Hori、Ikegami

  DOI：——

  日期：——
• Konstantinović; Dimitrijević; Radulović, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 3, p. 598 - 603
  作者：Konstantinović、Dimitrijević、Radulović

  DOI：——

  日期：——
• Wilhelm, Falk; Chatterjee, Swapan Kumar; Rattay, Bernd, Liebigs Annalen, 1995, # 9, p. 1673 - 1680
  作者：Wilhelm, Falk、Chatterjee, Swapan Kumar、Rattay, Bernd、Nuhn, Peter、Benecke, Renate、Ortwein, Jutta

  DOI：——

  日期：——