N,O,O-triacetyl-D-threo-C18-dihydrosphingosine | 35301-21-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,O,O-triacetyl-D-threo-C18-dihydrosphingosine
• 英文别名: triacetyl-D-threo-dihydrosphingosine；L_S-threo-1,3-diacetoxy-2-acetylamino-octadecane；L_S-threo-1,3-Diacetoxy-2-acetylamino-octadecan；(2R,3R)-1,3-Diacetoxy-2-acetylamino-octadecan；[(2R,3R)-2-acetamido-3-acetyloxyoctadecyl] acetate
• CAS: 35301-21-4
• 化学式: C₂₄H₄₅NO₅
• 分子量: 427.625
• InChiKey: WZSNFVBDKZJHSX-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  30.0
• 可旋转键数：
  19.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N,O,O-triacetyl-D-threo-C18-dihydrosphingosine 在 氢氧化钾 作用下， 生成 N-((2R,3R)-1,3-dihydroxyoctadecan-2-yl)acetamide
  参考文献：
  名称：

  Sticht et al., 1972, vol. 8, p. 10,17,22

  摘要：

  DOI：
• 作为产物：
  描述：

  正十四烷基三苯基溴化膦 在 盐酸 、 正丁基锂 、 氢气 、 二苯二硫醚 作用下， 生成 N,O,O-triacetyl-D-threo-C18-dihydrosphingosine
  参考文献：
  名称：

  Synthesis of two pairs of enantiomeric C18-sphingosines

  摘要：

  DOI：

  10.1016/s0040-4039(01)93935-8

文献信息

• Sphingolipids and Glycerolipids. Part II. Syntheses of Two Pairs of Enantiomeric C18-Sphingosines and a Palmitoyl Analogue of Gaucher Spleen Glucocerebroside.
  作者：Hirotaka SHIBUYA、Keiko KAWASHIMA、Norihiko NARITA、Masahiko IKEDA、Isao KITAGAWA

  DOI：10.1248/cpb.40.1154

  日期：——

  Sixteen kinds of chiral C4-epoxides [(-)-10a-d, (+)-10a-d, (-)-11a-d, (+)-11a-d], which are synthons in our synthetic strategy for complex lipids, have been prepared from (2Z)-2-butene-1, 4-diol (6) by employing a Sharpless asymmetric epoxidation. By using the chiral C4-epoxides [(+)-10a, (-)-10a, (-)-11a, (+)-11a] as starting compounds, two pairs of enantiomeric (D-erythro, L-erythro, D-threo, and L-threo)-C18-sphingosines (1, 2, 3, 4) have been synthesized via a regioselective ring-opening of the epoxide ring with azide anion followed by reduction of the azide group to an amino group and a Wittig reaction. Furthermore, D-erythro-C18-sphingosine (1) has been converted to a palmitoyl analogue (5a) of Gaucher spleen glucocerebroside (5) through a reaction pathway including successive condensations with palmitic acid and D-glucose.

  已合成十六种手性C4-环氧化物 [(-)-10a-d, (+)-10a-d, (-)-11a-d, (+)-11a-d]，这些化合物是我们合成复杂脂质策略中的合成子，通过使用Sharpless不对称环氧化反应，从(2Z)-2-丁烯-1, 4-二醇(6)制备而成。利用手性C4-环氧化物 [(+)-10a, (-)-10a, (-)-11a, (+)-11a] 作为起始化合物，通过环氧环的区域选择性开环反应与叠氮阴离子结合，随后将叠氮基团还原为氨基，并进行Wittig反应，合成了两对对映异构体（D-赤藓糖，L-赤藓糖，D-反式，L-反式）C18-鞘氨醇（1, 2, 3, 4）。此外，D-赤藓糖-C18-鞘氨醇（1）通过与棕榈酸和D-葡萄糖的连续缩合反应途径转化为高雪氏脾脏葡萄糖苷脂（5）的棕榈酰类似物（5a）。
• Molecular Interactions and Functional Interference between Vitronectin and Transforming Growth Factor-β
  作者：Michael Schoppet、Triantafyllos Chavakis、Nadia Al-Fakhri、Sandip M Kanse、Klaus T Preissner

  DOI：10.1038/labinvest.3780393

  日期：2002.1

  Different extracellular matrix proteins have been described as binding proteins for growth factors, influencing their storage or presentation towards cellular receptors. The multifunctional adhesive glycoprotein vitronectin (VN), which is found in the circulation and widely distributed throughout different tissues, has been implicated in the regulation of vascular cell functions, and these activities could be related to interactions with various growth factors. In vitro, soluble VN interfered with transforming growth factor-beta (TGF-beta) binding to isolated extracellular matrix and was found to associate with TGF-beta1 and TGF-beta2 as well as with other growth factors such as vascular endothelial growth factor, epidermal growth factor, or basic fibroblast growth factor in a saturable manner. In particular, binding of TGF-beta was maximal for the heparin-binding multimeric isoform of VN, whereas VN in a ternary complex with thrombin and antithrombin or plasma VN exhibited weaker binding. Plasminogen activator inhibitor-1 (PAI-1) or heparin, but not desulfated glycosaminoglycans, interfered with binding of VN to TGF-beta, and soluble PAI-1 was able to dissociate VN-bound TGF-beta. Upon limited plasmin proteolysis of VN, only the fragments comprising the intact aminoterminal portion of VN bound to TGF-beta as did a synthetic peptide (amino acids 43 to 62), indicating that TGF-beta and PAI-1 share common binding site(s) on VN. Although VN did not influence TGF-beta bioactivity for mink lung epithelial cells, TGF-beta dose dependently inhibited both urokinase-receptor as well as alpha(v)-integrin-dependent adhesion to VN. This activity of TGF-beta was reminiscent of the antiadhesive function of PAI-1. In atherosclerotic tissue sections, staining patterns of VN and TGF-beta indicated their colocalization. These findings describe VN as a new binding protein for TGF-beta, whereby specific functions of both factors become modulated by this interaction.
• SHIBUYA, HIROTAKA;KAWASHIMA, KEIKO;IKEDA, MASAHIKO;KITAGAWA, ISAO, TETRAHEDRON LETT., 30,(1989) N1, C. 7205-7208
  作者：SHIBUYA, HIROTAKA、KAWASHIMA, KEIKO、IKEDA, MASAHIKO、KITAGAWA, ISAO

  DOI：——

  日期：——