N-palmitoylsuccinimide | 56776-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-palmitoylsuccinimide
• 英文别名: N-(palmitoyloxy)succinimide；N-succinimidylpalmitate；1-Hexadecanoylpyrrolidine-2,5-dione
• CAS: 56776-06-8
• 化学式: C₂₀H₃₅NO₃
• 分子量: 337.503
• InChiKey: KHKNVXNSFCIZFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-palmitoylsuccinimide 在 咪唑 、 三乙胺 、 三氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 (S)-N-palmitoyl-O-H-phosphonate-serine tert-butyl ester
  参考文献：
  名称：

  N-酰基-O-磷酸胆碱脂氨酸：新型脂质结构，是尼曼-皮克C1病的生物标记。

  摘要：

  尼曼-匹克病C1型（NPC1）是一种致命的神经退行性胆固醇存储障碍。随着临床试验中新疗法的出现，迫切需要利用生物标记物改善诊断水平并监测疗效。在这项研究中，我们试图用m / z 509.3351的[M + H] +离子（以前称为lysoSM-509）定义NPC1未知脂质生物标记的结构。基于质谱分析和化学衍生化的结果，提出了用于脂质生物标志物的N-棕榈酰-O-磷酸胆碱化赖氨酸（PPCS）结构。由于没有商业标准，因此化学合成了正宗的PPCS，并使用液相色谱-串联质谱（LC-MS / MS）通过比较内源性化合物和合成化合物及其衍生物来确定结构。PPCS是N-酰基-O-磷酸胆碱脂蛋白（APCS）中最丰富的物种，APCS是一类以前从未在生物样品中检测到的脂质。进一步的分析表明，在NPC1血浆中，所有具有C14至C24酰基的APCS种类均升高。在NPC1猫模型的中央和周围组织中，PPCS也升高。APC

  DOI：

  10.1194/jlr.ra119000157
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 棕榈酸 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 N-palmitoylsuccinimide
  参考文献：
  名称：

  Fatty acid-binding site environments of serum vitamin D-binding protein and albumin are different

  摘要：

  Vitamin D-binding protein (DBP) and albumin (ALB) are abundant serum proteins and both possess high-affinity binding for saturated and unsaturated fatty acids. However, certain differences exist. We surmised that in cases where serum albumin level is low, DBP presumably can act as a transporter of fatty acids. To explore this possibility we synthesized several alkylating derivatives of 14 C-palmitic acid to probe the fatty acid-binding pockets of DBP and ALB. We observed that N-ethyl-5-phenylisooxzLzolium-3'-sulfonate-ester (WRX-ester) of C-14-palmitic acid specifically labeled DBP; but p-nitrophenyl- and N-hydroxysuccinimidyl-esters failed to do so. However, p-nitrophenyl ester of C-14-palmitic acid specifically labeled bovine ALB, indicating that the micro-environment of the fatty acid-binding domains of DBP and ALB may be different; and DBP may not replace ALB as a transporter of fatty acids. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2008.02.002

文献信息

• Physicochemical Studies on the Phospholipid Bilayer Incorporated.
  作者：Hideo KANEKO、Naokazu MURAHASHI、Atsushi SASAKI、Harutami YAMADA、Masahiro SAKAGAMI、Masahiro IKEDA

  DOI：10.1248/cpb.45.951

  日期：——

  With the intention of obtaining a novel liposome as a drug carrier able to avoid clearance by the reticuloendothelial system (RES), the authors synthesized two sialoglycolipids, i.e., 2-O-(8-hexadecanoylamino-3, 6-dioxaoctyl)-β-N-acetylneuraminic acid sodium salt (Sia-t-pa) and 2-O-[8-(2-hexadecyloctadecanoylamino)-3, 6-dioxaoctyl]-β-N-acetylneuraminic acid sodium salt (Sia-t-psa) and modified the surface of their liposomal membrane.Sia-t-pa was found to be eluted from the liposomal membrane by serum albumin, whereas Sia-t-psa was not, using the gel filtration method. In order to clarify the reason why there was such a difference between Sia-t-pa and Sia-t-psa, we investigated the properties of the phospholipid bilayer-incorporated sialoglycolipids physicochemically.The effect of the anchor structure of the sialoglycolipids, i.e., single acyl chain (Sia-t-pa) or double acyl chain (Sia-t-psa), on the fluidity and calorimetric properties was noticeably different. It was inferred that the effect was attributable to a difference in the position of the sialoglycolipid incorporated in the bilayer membrane.

  为了获得一种新型脂质体作为药物载体，以避免被网状内皮系统（RES）清除，作者合成了两种sialoglycolipids，即：2-O-(8-hexadecanoylamino-3, 6-dioxaoctyl)-β-N-乙酰神经氨酸钠盐（Sia-t-pa）、2-O-(8-hexadecyloctadanoylamino-3, 6-dioxaoctyl)-β-N-acetylneuraminic acid sodium salt (Sia-t-pa)和 2-O-[8-(2-hexadecyloctadanoylamino)-3, 6-dioxaoctyl]-β-N-acetylneuraminic acid sodium salt (Sia-t-psa)，并对其脂质体膜表面进行了修饰。使用凝胶过滤法发现，血清白蛋白能从脂质体膜上洗脱 Sia-t-pa，而 Sia-t-psa 却不能。为了弄清 Sia-t-pa 和 Sia-t-psa 之间存在这种差异的原因，我们从理化角度研究了磷脂双分子层包合的硅氧烷糖脂的特性。硅氧烷糖脂的锚结构（即单酰基链（Sia-t-pa）或双酰基链（Sia-t-psa））对流动性和热量特性的影响明显不同。据推断，这种影响可归因于双分子层膜中的酰基糖脂的位置不同。
• Heissschmelzdruckfarbe
  申请人：Siegwerk Druckfarben GmbH & Co. KG

  公开号：EP1118644A2

  公开（公告）日：2001-07-25

  Gegenstand der Erfindung ist eine Heißschmelzdruckfarbe, insbesondere für Tiefdruckverfahren, enthaltend a. 50 bis 80 Gew.-% Lösemittel mit einem Schmelzpunkt von 65 bis 109 Grd C und einer Viskosität von 2,9 bis 20 mPas bei 110 Grd C b. 20 bis 50 Gew.-% Bindemittel mit einer Glasübergangstemperatur TG von 30 bis 65 Grd C Ein weiterer Gegenstand der Erfindung ist eine Verwendung der Heißschmelzdruckfarbe.

  本发明的主题是一种热熔印刷油墨，特别是用于凹版印刷工艺，包括 a. 50 至 80 wt.% 溶剂，熔点为 65 至 109 Grd C，110 Grd C 时粘度为 2.9 至 20 mPas b.20 至 50 重量百分比的粘合剂，玻璃化温度 TG 为 30 至 65 摄氏度 本发明的另一个目的是热熔印刷油墨的用途。
• Glycosynthase-Mediated Synthesis of Glycosphingolipids
  作者：Mark D. Vaughan、Karl Johnson、Shawn DeFrees、Xiaoping Tang、R. Antony J. Warren、Stephen G. Withers

  DOI：10.1021/ja058469n

  日期：2006.5.1

  Glycosphingolipids play crucial roles in virtually every stage of the cell cycle, and their clinical administration has been proposed as a treatment for Alzheimer's, Parkinson's, stroke, and a range of other conditions. However, lack of supply has severely hindered testing of this potential. A novel glycosynthase-based synthetic strategy is demonstrated, involving a mutant of an endoglycoceramidase in which the catalytic nucleophile has been ablated. This mutant efficiently couples a range of glycosyl fluoride donors with a range of sphingosine-based acceptors in yields around 95%. This technology opens the door to large-scale production of glycosphingolipids and, thus, to clinical testing.
• N-acyl-O-phosphocholineserines: structures of a novel class of lipids that are biomarkers for Niemann-Pick C1 disease
  作者：Rohini Sidhu、Yawo Mondjinou、Mingxing Qian、Haowei Song、Arun Babu Kumar、Xinying Hong、Fong-Fu Hsu、Dennis J. Dietzen、Nicole M. Yanjanin、Forbes D. Porter、Elizabeth Berry-Kravis、Charles H. Vite、Michael H. Gelb、Jean E. Schaffer、Daniel S. Ory、Xuntian Jiang

  DOI：10.1194/jlr.ra119000157

  日期：2019.8

  disease type C1 (NPC1) is a fatal, neurodegenerative, cholesterol storage disorder. With new therapeutics in clinical trials, there is an urgency to improve diagnostics and monitor therapeutic efficacy with biomarkers. In this study, we sought to define the structure of an unknown lipid biomarker for NPC1 with [M + H]+ ion at m/z 509.3351, previously designated as lysoSM-509. The structure of N-palmi

  尼曼-匹克病C1型（NPC1）是一种致命的神经退行性胆固醇存储障碍。随着临床试验中新疗法的出现，迫切需要利用生物标记物改善诊断水平并监测疗效。在这项研究中，我们试图用m / z 509.3351的[M + H] +离子（以前称为lysoSM-509）定义NPC1未知脂质生物标记的结构。基于质谱分析和化学衍生化的结果，提出了用于脂质生物标志物的N-棕榈酰-O-磷酸胆碱化赖氨酸（PPCS）结构。由于没有商业标准，因此化学合成了正宗的PPCS，并使用液相色谱-串联质谱（LC-MS / MS）通过比较内源性化合物和合成化合物及其衍生物来确定结构。PPCS是N-酰基-O-磷酸胆碱脂蛋白（APCS）中最丰富的物种，APCS是一类以前从未在生物样品中检测到的脂质。进一步的分析表明，在NPC1血浆中，所有具有C14至C24酰基的APCS种类均升高。在NPC1猫模型的中央和周围组织中，PPCS也升高。APC
• Fatty acid-binding site environments of serum vitamin D-binding protein and albumin are different
  作者：Narasimha Swamy、Rahul Ray

  DOI：10.1016/j.bioorg.2008.02.002

  日期：2008.6

  Vitamin D-binding protein (DBP) and albumin (ALB) are abundant serum proteins and both possess high-affinity binding for saturated and unsaturated fatty acids. However, certain differences exist. We surmised that in cases where serum albumin level is low, DBP presumably can act as a transporter of fatty acids. To explore this possibility we synthesized several alkylating derivatives of 14 C-palmitic acid to probe the fatty acid-binding pockets of DBP and ALB. We observed that N-ethyl-5-phenylisooxzLzolium-3'-sulfonate-ester (WRX-ester) of C-14-palmitic acid specifically labeled DBP; but p-nitrophenyl- and N-hydroxysuccinimidyl-esters failed to do so. However, p-nitrophenyl ester of C-14-palmitic acid specifically labeled bovine ALB, indicating that the micro-environment of the fatty acid-binding domains of DBP and ALB may be different; and DBP may not replace ALB as a transporter of fatty acids. (C) 2008 Elsevier Inc. All rights reserved.