6-O-<(2R,3R)-3-hydroxy-2-tetradecyloctadecanoyl>-α,α-trehalose | 62054-35-7

• 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: 6-O-<(2R,3R)-3-hydroxy-2-tetradecyloctadecanoyl>-α,α-trehalose
• 英文别名: Trehalose 6-mono-corynomycolate；6-O-[(2R,3R)-3-hydroxy-2-tetradecyloctadecanoyl]-α,α'-trehalose；6-O-(2''R,3''R)-3''-hydroxy-2''-tetradecyloctadecanoyltrehalose；TMCM；[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl (2R,3R)-3-hydroxy-2-tetradecyloctadecanoate
• CAS: 62054-35-7
• 化学式: C₄₄H₈₄O₁₃
• 分子量: 821.143
• InChiKey: MNBUNKPMKFIPAD-GKDSKYAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  57
• 可旋转键数：
  35
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  216
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  2,2',3,3',4,4'-hexa-O-benzyl-6-O-(2''R,3''R)-3''-hydroxy-2''-tetradecyloctadecanoyltrehalose 在 20% palladium hydroxide-activated charcoal 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.5h， 以83%的产率得到6-O-<(2R,3R)-3-hydroxy-2-tetradecyloctadecanoyl>-α,α-trehalose
  参考文献：
  名称：

  Corynomycolic acid-containing glycolipids signal through the pattern recognition receptor Mincle

  摘要：

  葡萄糖单肉酰肌醇酸盐被发现可以通过小鼠和人类的Mincle信号传导。甘油单肉酰肌醇酸盐被证明可以选择性地通过人类的Mincle信号传导，其活性主要存在于2'的S异构体中。

  DOI：

  10.1039/c5cc00085h

文献信息

• An improved synthesis of trehalose 6-mono and 6,6′-dicorynomycolates and related esters
  作者：Arun K. Datta、Kuni Takayama、Mina A. Nashed、Laurens Anderson

  DOI：10.1016/0008-6215(91)84089-w

  日期：1991.9

  A simplified synthesis of 6-mono- and 6,6'-di-corynomycolate esters of alpha,alpha-trehalose, and related compounds, was achieved by coupling the (hydroxyl-protected) acids to the partially trimethylsilylated sugar in the presence of dicyclohexylcarbodiimide and 4-dimethylaminopyridine. As acid reactants, (2-RS,3-RS)-3-hydroxy-2-tetradecyloctadecanoic acid (DL-corynomycolic acid) and its 2RS,3SR diastereomer

  通过在二环己基碳二亚胺存在下将（羟基保护的）酸偶合到部分三甲基甲硅烷基化的糖上，可以简化α-，α-海藻糖和相关化合物的6-单-和6,6'-二-胭脂红酸酯的合成和4-二甲基氨基吡啶。（2-RS，3-RS）-3-羟基-2-十四烷基十五烷酸（DL-二十二烷酸）及其2RS，3SR非对映异构体是由棕榈酸甲酯通过连续Claisen缩合，还原，色谱分离和分离而制得的酸性反应物。皂化。与叔丁基氯二甲基硅烷（咪唑）反应，得到二取代的醚酯，通过部分水解将其转化为所需的3-叔丁基二甲基甲硅烷基醚。通过RS的反应获得了6联单硬脂酸高收率（78％），SR酸具有已知的七-O-（三甲基甲硅烷基）海藻糖，并且从等摩尔部分的RS，RS酸和六-O-（三甲基甲硅烷基）海藻糖获得高收率。过量（2.5摩尔份）的RS，RS酸得到6，6′-二酯（69％）。类似地，从（Me 3 Si）6-海藻糖获得单和双棕榈酸酯。单（RS，RS）-（Me
• Efficient Syntheses of a Series of Trehalose Dimycolate (TDM)/Trehalose Dicorynomycolate (TDCM) Analogues and Their Interleukin-6 Level Enhancement Activity in Mice Sera
  作者：Mugio Nishizawa、Hirofumi Yamamoto、Hiroshi Imagawa、Véronique Barbier-Chassefière、Emmanuel Petit、Ichiro Azuma、Dulce Papy-Garcia

  DOI：10.1021/jo062018j

  日期：2007.3.1

  We found an IL-6 level-enhancing compound during our synthetic study of trehalose-6,6'-dimycolate (1, TDM, formerly called cord factor) analogues. TDM is a glycolipid distributed in the cell wall of Mycobacterium tuberculosis and shows significant antitumor activity based on an immunoadjuvant activity. However, due to its significant toxicity, TDM is not yet applicable for practical use. In 1993, Datta and Takayama reported the purification of trehalose-6,6'-dicorynomycolate (2c, TDCM) from Corynebacterium spp. We have previously reported the synthesis of four diastereomeric TDCMs and showed that the synthetic (2R,3R,2'R,3'R)-TDCM (2c, hereafter abbreviated RRRR-TDCM-C-14) is identical to natural TDCM; we also demonstrated that 2c and SSSS-TDCM-C-14 (3c) showed significant antitumor activity as well as inhibitory activity in experimental lung metastasis based on the immunoadjuvant activity. Furthermore, we found that the significant lethal toxicity in mice by TDM (1) was no longer observed with the shorter-chain analogues of TDCMs. Therefore, we have elucidated that the 2,3-antistereochemistry (RR or SS) of the fatty acid residue is promising for biological activities. The chain length of the fatty acid residue should also be important for the biological activity, and thus, we designed a general synthetic procedure for trehalose diesters with 2,3-antistereochemistry and a series of chain lengths by using Noyori's asymmetric reduction of beta,beta-ketoesters followed by antiselective alkylation according to Frater to give beta,beta-hydroxy alcohols as the key steps. Thus, we prepared trehalose diesters (TDCM) 2a-d, 3a-d, and 4a-d as well as monoesters (TMCM) 5a-d and 6a-d. Immunological activities of TDCMs and TMCMs were evaluated by determining IL-6 level enhancement in mouse serum, and we found that RRRR-TDCM-C-14 (2c) and RRSS-TDCM-C-14 (4c) showed significant IL-6 level enhancement activities.
• Corynomycolic acid-containing glycolipids signal through the pattern recognition receptor Mincle
  作者：Phillip L. van der Peet、Christian Gunawan、Shota Torigoe、Sho Yamasaki、Spencer J. Williams

  DOI：10.1039/c5cc00085h

  日期：——

  Glucose monocorynomycolate is revealed to signal through both mouse and human Mincle. Glycerol monocorynomycolate is shown to selectively signal through human Mincle, with the activity residing predominantly in the 2′S-isomer.

  葡萄糖单肉酰肌醇酸盐被发现可以通过小鼠和人类的Mincle信号传导。甘油单肉酰肌醇酸盐被证明可以选择性地通过人类的Mincle信号传导，其活性主要存在于2'的S异构体中。