cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside | 168070-10-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl tetradecanoate
• CAS: 168070-10-8
• 化学式: C₄₇H₈₂O₇
• 分子量: 759.164
• InChiKey: WGLLNBXQHLWMOQ-HJUIBCSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  54
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-O-benzyl-D-glucopyranosyl N-phenyl-2,2,2-trifluoroacetimidate 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸 、 20% palladium hydroxide-activated charcoal 、 ammonium acetate 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 氯仿 、 环己烯 为溶剂， 反应 55.25h， 生成 cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Cholesteryl 6-O-acyl-α-glucosides from diverse Helicobacter spp. signal through the C-type lectin receptor Mincle

  摘要：

  具有立体选择性的胆固醇α-葡萄糖基化使得从不同的幽门螺杆菌（Helicobacter spp.）中合成胆固醇6-O-酰基葡萄糖苷成为可能，并且证明它们通过固有免疫受体Mincle发出信号。

  DOI：

  10.1039/d0ob01776k

文献信息

• Methods for the treatment and prevention of inflammatory diseases
  申请人：Umetsu Dale T.

  公开号：US09657046B2

  公开（公告）日：2017-05-23

  The inventors demonstrate that treatment of young, suckling mice with a glycolipid derived from Helicobacter pylori activates NKT cells in a CD1d-restricted fashion, and is protective against AHR in a model of allergen-induced asthma. The inventors further found that this protective effect can be transferred by NKT cells exposed to the glycolipid, and is associated with the expansion of a suppressive double-negative NKT cells and Foxp3+ TReg cells. The inventors also demonstrate herein that pre-treatment of adult mice with a glycolipid derived from Helicobacter pylori partially suppresses airway hyperreactivity and inhibits BAL inflammation in an ozone-exposure model. Accordingly, provided herein are compositions and methods for the treatment and prevention of inflammatory diseases, such as asthma or autoimmune diseases, in a subject in need thereof.

  发明者证明，用源自幽门螺杆菌的糖脂治疗幼年哺乳小鼠会以CD1d限制方式激活NKT细胞，并在过敏原诱导的哮喘模型中对AHR具有保护作用。发明者进一步发现，这种保护效应可以通过暴露于糖脂的NKT细胞转移，并与抑制性双阴性NKT细胞和Foxp3+ TReg细胞的扩增相关。发明者还在此证明，用源自幽门螺杆菌的糖脂对成年小鼠进行预处理部分抑制气道高反应性，并在臭氧暴露模型中抑制BAL炎症。因此，本文提供了用于治疗和预防炎症性疾病（如哮喘或自身免疫疾病）的组合物和方法，适用于需要的受试者。
• Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-α-d-glucopyranoside: a product of host cholesterol efflux promoted by Helicobacter pylori
  作者：Ryan A. Davis、Chun-Hung Lin、Jacquelyn Gervay-Hague

  DOI：10.1039/c2cc33948j

  日期：——

  In a three-step protocol involving regioselective enzymatic acylation, per-O-trimethylsilylation, and a one-pot α-glycosidation–deprotection sequence, cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside (α-CAG) of Helicobacter pylori is afforded starting from glucose in an overall yield of 45%. The production of CAG can be scaled to make purified quantities available to the biological community for the first time.

  在一项包含区域选择性酶促酧化、全-O-三甲基硅醻化和一步法α-糖肟化—脭护序列的三步方案中，从葡萄糖出发，以总体产率45%得到了幽门螺杆菌的胆固醇基-6-O-十四烷酰基-α-D-葡萄糖苷（α-CAG）。CAG的合成可以扩大规模，首次为生物学界提供纯化的量产。
• Cholesteryl glucosides signal through the carbohydrate recognition domain of the macrophage inducible C-type lectin (mincle)
  作者：Mattie S. M. Timmer、Thomas J. Teunissen、Kristel Kodar、Amy J. Foster、Sho Yamasaki、Bridget L. Stocker

  DOI：10.1039/d0ob02342f

  日期：——

  response, they are thought to play a role in the development of gastric atrophy. Herein, we prepared the first library of steryl D-glucosides and determined that they preferentially signal through the carbohydrate recognition domain of human Mincle, rather than the amino acid consensus motif. Lipidated steryl D-glucosides exhibited enhanced Mincle agonist activity, with C18 cholesteryl 6-O-acyl-α-D-glucoside

  胆固醇α- D-葡萄糖苷（αGCs）是引起癌症的人类病原体幽门螺杆菌的独特代谢产物。通过巨噬细胞可诱导的C型凝集素（Mincle）的信号传导和促炎反应的诱导，它们被认为在胃萎缩的发生中起作用。本文中，我们制备了第一个甾基D-葡萄糖苷文库，并确定它们优先通过人Mincle的碳水化合物识别结构域而不是氨基酸共有基序发出信号。脂化的甾基D-葡萄糖苷具有增强的Mincle激动剂活性，C18胆固醇基6 - O-酰基-α- D-葡萄糖苷（2c）是人类单核细胞最有效的激活剂。尽管表现出强烈的Mincle信号转导，但西多（5b）和豆甾醇（6b）导致原代细胞中较差的炎症反应，表明Mincle是预防幽门螺杆菌介导的炎症和癌症的潜在治疗靶标。
• Metabolic Isolation, Stereochemical Determination, and Total Synthesis of Predominant Native Cholesteryl Phosphatidyl-α-glucoside from Carcinogenic <i>Helicobacter pylori</i>
  作者：Chia-Chen Chang、Hau-Ming Jan、Chieh-Jen Tseng、Soumik Mondal、Andualem Bahiru Abera、Ming-Yen Hsieh、Tsai-Chen Yang、Sasikala Muthusamy、Sheng-Cih Huang、Chun-Hung Lin、Kwok-Kong Tony Mong

  DOI：10.1021/acs.orglett.2c01815

  日期：2022.7.22

  cholesteryl 6-O-phosphatidyl α-glucoside (CPG) from Helicobacter pylori via an integrated biological and chemical strategy. The strategy employed (i) the metabolic isolation of a CPG analogue and (ii) the enzymatic degradation of the analogue to obtain the native lactobacillic acid for the stereochemical determination. The absolute stereochemistry of the acid was found to be 11R and 12S. Using the new

  我们报告了通过综合生物和化学策略从幽门螺杆菌中分离和立体化学测定主要的天然胆固醇 6 - O-磷脂酰 α-葡萄糖苷 (CPG) 。该策略采用 (i) CPG 类似物的代谢分离和 (ii) 类似物的酶促降解以获得用于立体化学测定的天然乳杆菌酸。发现酸的绝对立体化学为 11 R和 12 S。使用新的立体化学数据，我们完成了主要天然 CPG 和其他主要 αCG 衍生物的全合成。
• Tandem Glycosyl Iodide Glycosylation and Regioselective Enzymatic Acylation Affords 6-<i>O</i>-Tetradecanoyl-α-<scp>d</scp>-cholesterylglycosides
  作者：Ryan A. Davis、James C. Fettinger、Jacquelyn Gervay-Hague

  DOI：10.1021/jo501371h

  日期：2014.9.5

  A generalized synthesis of α-d-cholesterylglycosides has been achieved using one-pot per-O-trimethylsilyl glycosyl iodide glycosidation. Both cholesteryl α-d-glucopyranoside (αCG) and cholesteryl α-d-galactopyranoside were prepared in high yield. These compounds were further esterified using regioselective enzymatic acylation with tetradecanoyl vinyl ester to afford 6-O-tetradecanoyl-α-d-cholesteryl glucopyranoside (αCAG) of Helicobacter pylori and the corresponding galactose analogue in 66-78% overall yields from free sugars. The tandem step-economy sequence provides novel analogues to facilitate glycolipidomic profiling.