(2S,3S,4R)-1-O-(α-D-galactopyranosyl)-2-(N-tetracosanoylamino)-1,3,4-nonanetriol | 383187-82-4

• 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: (2S,3S,4R)-1-O-(α-D-galactopyranosyl)-2-(N-tetracosanoylamino)-1,3,4-nonanetriol
• 英文别名: (2S,3S,4R)-1-O-(α-D-galactopyranosyl)-2-tetracosanoylamino-1,3,4-nonanetriol；(2S,3S,4R)-1-(α-D-galactopyranosyloxy)-2-tetracosanoylaminononane-3,4-diol；(2S,3S,4R)-1-O-(α-D-galactosyl)-2-(N-tetracosanoylamino)-1,3,4-nonanetriol；(2S,3S,4R)-1-(α-D-galactopyranosyl)-2-(tetracosanoylamino)nonan-3,4-diol；PBS20；OCH；1-O-(alpha-D-galactopyranosyl)-N-tetracosanyl-2-aminononane-1,3,4-triol；N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynonan-2-yl]tetracosanamide
• CAS: 383187-82-4
• 化学式: C₃₉H₇₇NO₉
• 分子量: 704.042
• InChiKey: MPKIDHIOYNMFES-CLTBVUQJSA-N

物化性质

• 熔点：
  125-127 °C
• 沸点：
  861.8±65.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  49
• 可旋转键数：
  33
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-1-O-(α-D-galactopyranosyl)-2-(N-tetracosanoylamino)-1,3,4-nonanetriol 在 水 作用下， 以 乙醇 为溶剂， 生成 2-tetracosanoylamino-1-O-α-D-galactopyranosyl-D-ribo-1,3,4-nonanetriol 1-hydrate
  参考文献：
  名称：

  GLYCOLIPID DERIVATIVES, PROCESS FOR PRODUCTION OF THE SAME, INTERMEDIATES FOR SYNTHESIS THEREOF, AND PROCESS FOR PRODUCTION OF THE INTERMEDIATES

  摘要：

  公开号：

  EP1619199B1
• 作为产物：
  描述：

  D-Arabitol 在 palladium dihydroxide 、 Lindlar's catalyst 吡啶 、 盐酸 、 copper(l) iodide 、 sodium azide 、 三氟化硼乙醚 、 potassium tert-butylate 、 氢气 、 二正丁基氧化锡 、 1-羟基苯并三唑 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 175.0h， 生成 (2S,3S,4R)-1-O-(α-D-galactopyranosyl)-2-(N-tetracosanoylamino)-1,3,4-nonanetriol
  参考文献：
  名称：

  免疫抑制性糖脂（2S，3S，4R）-1 - O-（α-d-半乳糖基）-2-四cosanoylamino-1,3,4-壬三醇的全合成

  摘要：

  实用有效的全合成（2S，3S，4R）-1- O-（α - d-半乳糖基）-2-四cosanoylamino-1,3,4-壬三醇OCH 1b（Th1介导的潜在治疗候选物）描述了自身免疫性疾病。该合成将直接烷基化结合到环氧化物5上，并通过立体特异性卤化物离子催化的α-糖基化反应。从市售的d-阿拉伯糖醇2和1b的总合成中，仅需八步即可获得关键中间体10，总收率达到37％。分12步完成，总收率19％。该方法将能够以高度立体选择性的方式合成多种植物鞘氨醇脂，特别是具有比1a短的鞘氨醇侧链的植物鞘氨醇脂。

  DOI：

  10.1021/jo048151y

文献信息

• Novel synthesis of α-galactosyl-ceramides and confirmation of their powerful NKT cell agonist activity
  作者：Adrianne Lee、Kathryn J. Farrand、Nina Dickgreber、Colin M. Hayman、Stefan Jürs、Ian F. Hermans、Gavin F. Painter

  DOI：10.1016/j.carres.2006.09.006

  日期：2006.12

  identified as a powerful modulator of immunological processes through its capacity to bind CD1d molecules and specifically activate invariant natural killer (NK)-like T cells (iNKT cells). This paper describes the synthesis of 1, the analogous alpha-galactosyl-ceramide 3, and its short chain analogue 'OCH' (2), by use of the 4,6-di-O-tert-butylsilylene (DTBS) protecting group to produce a powerful alpha-galactosylating

  α-半乳糖苷神经酰胺（1）通过结合CD1d分子并特异性激活不变的自然杀伤（NK）样T细胞（iNKT细胞），已被认为是免疫过程的有力调节剂。本文通过使用4,6-二-O-叔丁基亚甲硅烷基（DTBS）保护基来描述1，类似的α-半乳糖基神经酰胺3及其短链类似物'OCH'（2）的合成产生强大的α-半乳糖基化剂。体内实验证实这些化合物以CD1d依赖性方式是iNKT细胞的有效和选择性激活剂，每种诱导细胞因子释放的独特过程。这种合成策略将允许产生新的衍生物，用于研究iNKT细胞活化的机制。
• ORGANIC COMPOUNDS
  申请人：Callaghan Innovation Research Limited

  公开号：US20150191503A1

  公开（公告）日：2015-07-09

  This invention relates to sphingoglycolipid analogues, compositions comprising these compounds, processes for preparing the compounds, and methods of treating or preventing diseases or conditions using the compounds, such as diseases or conditions relating to infection, atopic disorders, autoimmune disease, diabetes or cancer.

  本发明涉及鞘氨醇糖脂类似物，包括这些化合物的组合物，制备这些化合物的方法，并使用这些化合物治疗或预防与感染、变态反应性疾病、自身免疫疾病、糖尿病或癌症相关的疾病或病况的方法。
• Memory invariant NKT cell marker
  申请人：RIKEN

  公开号：US10416160B2

  公开（公告）日：2019-09-17

  The present invention provides use of KLRG1 as a marker specific to memory invariant NKT cells. Using an antibody that specifically recognizes KLRG1, memory invariant NKT cells can be easily detected or isolated.

  本发明将 KLRG1 用作记忆不变 NKT 细胞的特异性标记。使用特异性识别 KLRG1 的抗体，可轻松检测或分离记忆不变 NKT 细胞。
• Synthesis and Evaluation of Sphinganine Analogues of KRN7000 and OCH
  作者：Rachel M. Ndonye、Douglas P. Izmirian、Matthew F. Dunn、Karl O. A. Yu、Steven A. Porcelli、Archana Khurana、Mitchell Kronenberg、Stewart K. Richardson、Amy R. Howell

  DOI：10.1021/jo051147h

  日期：2005.12.1

  The phytosphingosine-containing alpha-galactosylceramides (alpha-GalCers), KRN7000 and OCH, have been shown to activate NKT cells via interaction with CD1d, a member of the CD1 family of antigen presenting proteins. Evidence from KRN7000 stimulation of NKT cells suggests that alpha-GalCers may have applications in the treatment or prevention of a range of viral, bacterial, and autoimmune conditions. Moreover, OCH, a truncated analogue of KRN7000, appears to induce a T(H)2 bias, which could have implications for the treatment of autoimmune and inflammatory conditions. We have prepared the direct sphinganine-containing analogues of KRN7000 and OCH, 1 and 2, and found them to be comparable in activity to the parent compounds in inducing the release of IL-2, IL-4, and IFN gamma. In addition, compound 2 leads to a cytokine bias similar to that seen with OCH. This is significant because sphinganines are more easily accessed than phytosphingosines, which should facilitate SAR studies.
• RCAI-17, 22, 24–26, 29, 31, 34–36, 38–40, and 88, the analogs of KRN7000 with a sulfonamide linkage: Their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines
  作者：Takuya Tashiro、Naomi Hongo、Ryusuke Nakagawa、Ken-ichiro Seino、Hiroshi Watarai、Yasuyuki Ishii、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.bmc.2008.08.060

  日期：2008.10

  RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 (1) with a sulfonamide linkage instead of an amide bond, were synthesized to examine their bioactivity for mouse natural killer (NK) T cells. RCAI-17, 22, 24-26, 29, 31, 34-36, and 88 are the aromatic sulfonamide analogs, while RCAI-39 and 40 are the aliphatic ones. RCAI-38 is a C-galactoside analog of RCAI-26, which is the p-toluenesulfonamide analog of KRN7000. According to their bioassay, these sulfonamide analogs were shown to be the stimulants of mouse NKT cells to induce the production of Th2-biased cytokines in vitro, while RCAI-38 did not induce any cytokine production. (C) 2008 Elsevier Ltd. All rights reserved.