(2R)-2-amino-hexadecanol | 184850-77-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R)-2-amino-hexadecanol
• 英文别名: (2R)-2-aminohexadecan-1-ol；(R)-2-aminohexadecanol；1-Hexadecanol, 2-amino-, (2R)-
• CAS: 184850-77-9
• 化学式: C₁₆H₃₅NO
• 分子量: 257.46
• InChiKey: MNGRWBQCRJBGSJ-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-2-amino-hexadecanol 、 棕榈酰氯 在 吡啶 、 三甲基氯硅烷 作用下， 生成 Hexadecanoic acid ((R)-1-hydroxymethyl-pentadecyl)-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
• 作为产物：
  描述：

  在 sodium periodate 、 lithium aluminium tetrahydride 、 sodium azide 、 三氟乙酸 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 10.0h， 生成 (2R)-2-amino-hexadecanol
  参考文献：
  名称：

  从亚环己基甘油醛对映体合成一些生物活性氨基醇及相关化合物

  摘要：

  由一些对映异构纯的3-烷基甘油合成了两种生物活性氨基醇或相关衍生物2-氨基十六烷醇I和赤型-9-（2-羟基-3-壬基）腺嘌呤盐酸盐（EHNA盐酸盐）IIa。依次通过简单的格利雅（Grignard）加入环己叉基甘油醛1中，然后通过柱色谱法来制备所需的C-3表异构体3-烷基甘油。

  DOI：

  10.1016/s0957-4166(99)00059-2

文献信息

• 2-aminoalchohol immunosuppressants: Structure-activity relationships
  作者：Ryoji Hirose、Norimitsu Hamamichi、Yuuki Kitao、Tohru Matsuzaki、Kenji Chiba、Tetsuro Fujita

  DOI：10.1016/s0960-894x(96)00487-8

  日期：1996.11

  The 2-aminoalcohol series of immunosuppressants showed a bell-shaped relationship between the activity and the carbon number. The (R)-isomers were more potent than the (S)-isomers, and (R)-2-aminohexadecanol displayed comparably activity to a potent immunosuppressant, FTY720. Copyright (C) 1996 Elsevier Science Ltd
• Enantiospecific synthesis of some bioactive amino alcohols and related compounds from cyclohexylideneglyceraldehyde
  作者：Anubha Sharma、Subrata Chattopadhyay

  DOI：10.1016/s0957-4166(99)00059-2

  日期：1999.3

  Two bioactive amino alcohols or related derivatives, 2-aminohexadecanol I and erythro-9-(2-hydroxy-3-nonyl)adenine hydrochloride (EHNA hydrochloride) IIa, have been synthesized from some enantiomerically pure 3-alkylglycerols. The required C-3 epimeric 3-alkylglycerols were, in turn, prepared by simple Grignard addition to cyclohexylideneglyceraldehyde 1 followed by column chromatography.

  由一些对映异构纯的3-烷基甘油合成了两种生物活性氨基醇或相关衍生物2-氨基十六烷醇I和赤型-9-（2-羟基-3-壬基）腺嘌呤盐酸盐（EHNA盐酸盐）IIa。依次通过简单的格利雅（Grignard）加入环己叉基甘油醛1中，然后通过柱色谱法来制备所需的C-3表异构体3-烷基甘油。
• 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.