(2S,3S,4R)-2-amino-1,3,4-nonanetriol | 872356-77-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,3S,4R)-2-amino-1,3,4-nonanetriol
• 英文别名: (2S,3S,4R)-2-aminononane-1,3,4-triol
• CAS: 872356-77-9
• 化学式: C₉H₂₁NO₃
• 分子量: 191.271
• InChiKey: CKMWXJBZFFJHKX-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-2-amino-1,3,4-nonanetriol 在 吡啶 、 2,6-二甲基吡啶 、 四丁基氟化铵 、 水 、 silver perchlorate 、 三氟乙酸 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 (2S,3S,4R)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-(tetracosanoylamino)nonane-3,4-diol
  参考文献：
  名称：

  Synthesis and Evaluation of Sphinganine Analogues of KRN7000 and OCH

  摘要：

  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.

  DOI：

  10.1021/jo051147h
• 作为产物：
  描述：

  (2S,3S,4R)-2-azido-nonane-1,3,4-triol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 12.0h， 生成 (2S,3S,4R)-2-amino-1,3,4-nonanetriol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2008.08.060

文献信息

• Effects of Lipid Chain Lengths in α-Galactosylceramides on Cytokine Release by Natural Killer T Cells
  作者：Randal D. Goff、Ying Gao、Jochen Mattner、Dapeng Zhou、Ning Yin、Carlos Cantu、Luc Teyton、Albert Bendelac、Paul B. Savage

  DOI：10.1021/ja045385q

  日期：2004.10.1

  Glycolipid presentation by CD1 proteins has emerged as an important aspect of antigen recognition, and presentation of alpha-glycosylceramides by CD1d to natural killer T cells has become a central focus in understanding how glycolipid presentation can influence immune responses. An alpha-galactosylceramide containing relatively long lipid chains has been the subject of intense study because, when presented by CD1d to natural killer T cells, it stimulates the release of both proinflammatory and immunomodulatory cytokines. Using an efficient synthesis of alpha-galactosylceramides, we have prepared a series of glycolipids in which the lipid chain lengths have been incrementally varied. The responses of natural killer T cells to these glycolipids have been determined, and we have found that truncation of the phytosphingosine lipid chain increases the relative amounts of immunomodulatory cytokines released. In similar fashion, the length of the acyl chain in alpha-galactosylceramides influences cytokine release profiles.
• 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.