Hexadecanoic acid [3-(4-octyl-phenyl)-1-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-propyl]-amide | 903894-74-6

• 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: Hexadecanoic acid [3-(4-octyl-phenyl)-1-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-propyl]-amide
• 英文别名: N-[4-(4-octylphenyl)-1-[(2S,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxybutan-2-yl]hexadecanamide
• CAS: 903894-74-6
• 化学式: C₆₈H₉₅NO₇
• 分子量: 1038.5
• InChiKey: RAKPSDMOVAQHSO-AODJLLEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.6
• 重原子数：
  76
• 可旋转键数：
  41
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Hexadecanoic acid [3-(4-octyl-phenyl)-1-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-propyl]-amide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以33%的产率得到N-[1-(α-D-mannopyranosyl-oxymethyl)-3-(4-octylphenyl)propyl]hexadecanamide
  参考文献：
  名称：

  Induction of promotive rather than suppressive immune responses from a novel NKT cell repertoire Vα19 NKT cell with α-mannosyl ceramide analogues consisting of the immunosuppressant ISP-I as the sphingosine unit

  摘要：

  A 2-substituted 2-aminopropane-1,3-diol or 2-aminoethanol is the minimum structure required for the immunosuppressive activity of ISP-I, an antibiotic isolated from the culture broth of Isaria sinclairil. A series of alpha-mannosyl ceramide (alpha-ManCer) analogues was derived from 2-substituted 2-aminopropane-1,3-diols or 2-aminoethanols in place of sphingosine. The newly synthesized glycosides were evaluated for their effects on immune responses. In contrast to the immunosuppressive activity of the precursors, the a-ManCer analogues induced immunopromotive responses from invariant V alpha N-J alpha 26 transgenic mouse lymphocytes more effectively than the original a-ManCer. Collectively, it is strongly suggested that the 2-substituted 2-aminopropane-1,3-diols and 2-aminoethanols mimic sphingosine in the alpha-ManCer analogues so that they potentially acquire specific antigenicity toward V alpha 19 NKT cell, a novel NKT cell subset. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.11.013
• 作为产物：
  描述：

  (RS)-2-amino-4-(4-octylphenyl)butan-1-ol 在 吡啶 、 三甲基氯硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 Hexadecanoic acid [3-(4-octyl-phenyl)-1-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-propyl]-amide
  参考文献：
  名称：

  Induction of promotive rather than suppressive immune responses from a novel NKT cell repertoire Vα19 NKT cell with α-mannosyl ceramide analogues consisting of the immunosuppressant ISP-I as the sphingosine unit

  摘要：

  A 2-substituted 2-aminopropane-1,3-diol or 2-aminoethanol is the minimum structure required for the immunosuppressive activity of ISP-I, an antibiotic isolated from the culture broth of Isaria sinclairil. A series of alpha-mannosyl ceramide (alpha-ManCer) analogues was derived from 2-substituted 2-aminopropane-1,3-diols or 2-aminoethanols in place of sphingosine. The newly synthesized glycosides were evaluated for their effects on immune responses. In contrast to the immunosuppressive activity of the precursors, the a-ManCer analogues induced immunopromotive responses from invariant V alpha N-J alpha 26 transgenic mouse lymphocytes more effectively than the original a-ManCer. Collectively, it is strongly suggested that the 2-substituted 2-aminopropane-1,3-diols and 2-aminoethanols mimic sphingosine in the alpha-ManCer analogues so that they potentially acquire specific antigenicity toward V alpha 19 NKT cell, a novel NKT cell subset. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.11.013

文献信息

• Induction of promotive rather than suppressive immune responses from a novel NKT cell repertoire Vα19 NKT cell with α-mannosyl ceramide analogues consisting of the immunosuppressant ISP-I as the sphingosine unit
  作者：Michio Shimamura、Naoki Okamoto、Yi-Ying Huang、Jouji Yasuoka、Kenji Morita、Akira Nishiyama、Yuusuke Amano、Tadashi Mishina

  DOI：10.1016/j.ejmech.2005.11.013

  日期：2006.5

  A 2-substituted 2-aminopropane-1,3-diol or 2-aminoethanol is the minimum structure required for the immunosuppressive activity of ISP-I, an antibiotic isolated from the culture broth of Isaria sinclairil. A series of alpha-mannosyl ceramide (alpha-ManCer) analogues was derived from 2-substituted 2-aminopropane-1,3-diols or 2-aminoethanols in place of sphingosine. The newly synthesized glycosides were evaluated for their effects on immune responses. In contrast to the immunosuppressive activity of the precursors, the a-ManCer analogues induced immunopromotive responses from invariant V alpha N-J alpha 26 transgenic mouse lymphocytes more effectively than the original a-ManCer. Collectively, it is strongly suggested that the 2-substituted 2-aminopropane-1,3-diols and 2-aminoethanols mimic sphingosine in the alpha-ManCer analogues so that they potentially acquire specific antigenicity toward V alpha 19 NKT cell, a novel NKT cell subset. (c) 2006 Elsevier SAS. All rights reserved.