(2-aminoethyl) 4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 929034-07-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-aminoethyl) 4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: 2′-aminoethyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside；Glc2Ac3Ac4Ac6Ac(a1-4)Glc2Ac3Ac6Ac(b)-O-EtNH2；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-(2-aminoethoxy)-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 929034-07-1
• 化学式: C₂₈H₄₁NO₁₈
• 分子量: 679.629
• InChiKey: KMPCTBHKWIOALB-QACPWNKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.42
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  247.04
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  (2-aminoethyl) 4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.67h， 生成
  参考文献：
  名称：

  抗真菌八环肽Tunicyclin D的N-糖基化衍生物的合成及抗真菌活性

  摘要：

  通过高效和通用的合成方法合成了一系列的Tunicyclin D糖基化衍生物。该方法基于固相肽合成，其中2-氯三苯甲基树脂为固相载体，糖基氨基酸为结构单元。合成的Tunicyclin D衍生物的生物学研究表明，含单糖的化合物显示出改善的或相似的抗真菌活性，而带有二糖聚糖的化合物则显示出弱得多的抗真菌活性。

  DOI：

  10.1016/j.tet.2014.05.077
• 作为产物：
  描述：

  2-bromoethoxy (2,3,4,6-tetra-O-acetyl-D-glucopyranoside)-β(1→4)-2,3,4,6-tetra-O-acetyl-D-glucopyranoside 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 (2-aminoethyl) 4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  An Improved Synthetic Procedure for the Preparation of N‐Acyl (2‐aminoethyl)‐β‐d‐glycopyranoside Lipids and Characterization of Their Mesogenic Properties

  摘要：

  A modified synthetic procedure was used for the synthesis of N-acyl (2-aminoethyl) glycosides bearing lactose, maltose, and melibiose carbohydrate headgroups and different acyl chains. The lipid glycosides were prepared in gram scale and investigated for their liquid crystalline properties. It was found that the polar spacer suppresses polymorphism, and the resulting simplified phase behavior was found in the pure state upon heating, as well as for the lyotropic phases.

  DOI：

  10.1080/07328300601082385

文献信息

• Structural polymorphism of hydrated monoacylated maltose glycolipids
  作者：Jörg Howe、Patrick Garidel、Matthias Wulf、Sven Gerber、Götz Milkereit、Volkmar Vill、Manfred Roessle、Klaus Brandenburg

  DOI：10.1016/j.chemphyslip.2008.07.002

  日期：2008.9

  The physico-chemical properties of three fully hydrated monoacyl maltoside glycolipids were investigated with Fourier-transform infrared spectroscopy (FTIR), differential scanning calorimetry (DSC) and small-angle X-ray scattering (SAXS). The different synthesized maltoside glycoconjugates vary in the length and saturation of the fatty acid moiety, whereas the constant head group region contains a

  通过傅立叶变换红外光谱（FTIR），差示扫描量热法（DSC）和小角X射线散射（SAXS）研究了三种完全水合的单酰基麦芽糖苷麦芽糖苷的理化性质。不同的合成麦芽糖苷糖缀合物的长度和脂肪酸部分的饱和度各不相同，而恒定的头部基团区域则包含带有OC（2）-NH间隔基的β-连接的麦芽糖。考虑到所采用的分子的三维聚集结构以及酰基链的从凝胶相到液晶相的主相转变，具有饱和酰基链的化合物表现出复杂的温度依赖性行为模式。饱和酰基链被不饱和酰基链取代导致结构偏好的完全改变，从双层的高度有序堆叠到完全无序和流体膜的单层排列。与缺少NH基团的化合物相比，间隔基中NH基团的存在允许形成氢键网络，这会影响所观察到的相性质。讨论了水合单酰化麦芽糖糖脂的这些研究结果，与不存在水的情况下纯化合物的热致变相性质有关。
• SURFACTANT COMPOUNDS-CLIPS FOR EXTRACTION AND STABILIZATION IN SOLUTION OF MEMBRANE PROTEINS
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US20210130385A1

  公开（公告）日：2021-05-06

  The present invention relates to a compound of formula (I): (I) as defined in the description. The present invention also relates to a method for extracting biological membrane-associated membrane proteins, comprising a step of bringing an aqueous solution of biological membrane-associated membrane proteins into contact with at least one compound of the invention. The present invention also relates to a method for stabilizing membrane proteins in solution in an aqueous solution, comprising a step (i) consisting in bringing an aqueous solution of a membrane protein in solution into contact with at least one compound of the invention.

  本发明涉及式（I）的化合物：（I）如描述中所定义。本发明还涉及一种提取生物膜相关膜蛋白的方法，包括将生物膜相关膜蛋白的水溶液与本发明中的至少一种化合物接触的步骤。本发明还涉及一种在水溶液中稳定膜蛋白的方法，包括步骤（i）将膜蛋白的水溶液与本发明中的至少一种化合物接触。
• Surfactant compounds-clips for extraction and stabilization in solution of membrane proteins
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US11440932B2

  公开（公告）日：2022-09-13

  The present invention relates to a compound of formula (I): (I) as defined in the description. The present invention also relates to a method for extracting biological membrane-associated membrane proteins, comprising a step of bringing an aqueous solution of biological membrane-associated membrane proteins into contact with at least one compound of the invention. The present invention also relates to a method for stabilizing membrane proteins in solution in an aqueous solution, comprising a step (i) consisting in bringing an aqueous solution of a membrane protein in solution into contact with at least one compound of the invention.

  本发明涉及一种式 (I) 化合物：(I)的化合物。本发明还涉及一种提取生物膜相关膜蛋白的方法，包括使生物膜相关膜蛋白的水溶液与至少一种本发明化合物接触的步骤。本发明还涉及一种在水溶液中稳定溶液中膜蛋白的方法，包括使溶液中膜蛋白的水溶液与至少一种本发明化合物接触的步骤(i)。
• Saccharide-Functionalized Alkanethiols for Fouling-Resistant Self-Assembled Monolayers: Synthesis, Monolayer Properties, and Antifouling Behavior
  作者：Timmy Fyrner、Hung-Hsun Lee、Alberto Mangone、Tobias Ekblad、Michala E. Pettitt、Maureen E. Callow、James A. Callow、Sheelagh L. Conlan、Robert Mutton、Anthony S. Clare、Peter Konradsson、Bo Liedberg、Thomas Ederth

  DOI：10.1021/la202774e

  日期：2011.12.20

  We describe the synthesis of a series of mono-, di-, and trisaccharide-functionalized alkanethiols as well as the formation of fouling-resistant self-assembled monolayers (SAMs) from these. The SAls,,Is were characterized using ellipsometry, wetting measurements, and infrared reflection absorption spectroscopy (WAS). We show that the structure of the carbohydrate moiety affects the packing density and that this also alters the alkane chain organization. Upon increasing the size of the sugar moieties (from mono- to di- and trisaccharides), the structural qualities of the monolayers deteriorated with increasing disorder, and for the trisaccharide, slow reorganization dynamics in response to changes in the environmental polarity were observed. The antifouling properties of these SAMs were investigated through protein adsorption experiments from buffer solutions as well as settlement (attachment) tests using two common marine fouling species, zoospores of the green macroalga Ulva linza and cypris larvae of the barnacle Balanus amphitrite. The SAMs showed overall good resistance to fouling by both the proteins and the tested marine organisms. To improve the packing density of the SAMs with bulky headgroups, we employed mixed SAMs where the saccharide-thiols are diluted with a filler molecule having a small 2-hydroxyethyl headgroup. This method also provides a means by which the steric availability of sugar moieties can be varied, which is of interest for specific interaction studies with surface-bound sugars. The results of the surface dilution study and the low nonspecific adsorption onto the SAMs both indicate the feasibility of this approach.