maltopentaose lactone | 76707-51-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: maltopentaose lactone
• 英文别名: D-maltopentaono-1,5-lactone；(3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-one
• CAS: 76707-51-2
• 化学式: C₃₀H₅₀O₂₆
• 分子量: 826.711
• InChiKey: WZLSAIPXWOSENT-WVXRWCISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.6
• 重原子数：
  56
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  424
• 氢给体数：
  16
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  maltopentaose lactone 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1,5-bis-O-hexadecyl-N-maltopentaonoyl-L-glutamate
  参考文献：
  名称：

  Physical properties and packing states of molecular assemblies of synthetic glycolipids in aqueous dispersions

  摘要：

  合成了具有不同长度的两条碳氢链（碳数，m：14、16、18）和含有（葡萄糖单位，n：3、5、7）麦芽寡糖的酰胺糖脂--1,5-双-O-烷基-N-麦芽寡糖酰-L-谷氨酸（1），以及一种 N-糖苷脂--1,5-双-O-十八烷基-N-麦芽酮基-L-谷氨酸（2）。通过负染 TEM、冷冻 TEM 和原子力显微镜等显微镜观察分析了其组装结构。糖脂 1a（m,n：14,5）在所有观察温度下都呈现出纤维状结构，而糖脂 1b（16,5）在水合温度高于凝胶-液晶相转变温度（Tc；45°C）时呈现出纤维状结构，在低于 Tc 时则呈现出大圆盘状结构。糖脂 1c（18,5）在水合温度高于 Tc 时呈大圆盘状结构。糖脂 1d（18,3）和 1e（18,7）分别呈现出大圆盘和大囊泡的混合物以及小圆盘和胶束的混合物。没有酰胺连接的 N-糖苷脂质 2 只形成了囊泡结构。使用挤压和超声等高剪切应力的制备程序可将 1c 的大圆盘转化为较小的组装体，如小盘状、锥状和颗粒状组装体，具体取决于制备条件。圆盘平面部分的糖脂分子紧密堆积，即使在 Tc（58°C）以上，分子流动性也很低，糖链对康卡伐林 A 的反应活性也很低，这表明高反应活性可能来自于组装体边缘部分糖链的松散堆积。

  DOI：

  10.1039/a800289d
• 作为产物：
  描述：

  麦芽五糖 在 calcium carbonate 、 calcium bromide 作用下， 以 水 为溶剂， 反应 0.78h， 以90.2%的产率得到maltopentaose lactone
  参考文献：
  名称：

  Preparation of oligosaccharide aldonolactones and N-(2-aminoethyl)aldonamides

  摘要：

  DOI：

  10.1016/s0008-6215(00)85912-1

文献信息

• Cryoprotection of Synthetic Glycolipids for Phospholipid Vesicles
  作者：Hiromi Sakai、Mikimasa Takisada、Shinji Takeoka、Eishun Tsuchida

  DOI：10.1246/cl.1993.1891

  日期：1993.11

  The synthetic glycolipid; N-hexadecylmaltopentaonamide (HDMPA), was introduced as a component of a phospholipid vesicle (φ, ca. 100 nm) of 1,2-dipalmitoyl-sn-glycero-3-phosphorylcholine (DPPC) to modify the surface of the vesicle with oligosaccharide. After freeze-thawing, the size of the vesicles does not change, and the leakage of 5(6)-carboxyfluorescein encapsulated into the vesicles is suppressed

  合成糖脂；N-十六烷基麦芽五酰胺 (HDMPA) 作为 1,2-二棕榈酰-sn-甘油-3-磷酰胆碱 (DPPC) 的磷脂囊泡（φ，约 100 nm）的组分引入，用寡糖修饰囊泡的表面. 冻融后，囊泡的大小没有变化，并且包裹在囊泡中的 5(6)-羧基荧光素的泄漏受到抑制，表明糖脂具有冷冻保护活性。
• Structural Characterization of Glucooligosaccharide Oxidase from <i>Acremonium strictum</i>
  作者：Meng-Hwan Lee、Wen-Lin Lai、Shuen-Fuh Lin、Cheng-Sheng Hsu、Shwu-Huey Liaw、Ying-Chieh Tsai

  DOI：10.1128/aem.71.12.8881-8887.2005

  日期：2005.12

  Glucooligosaccharide oxidase from Acremonium strictum was screened for potential applications in oligosaccharide acid production and carbohydrate detection. This protein is a unique covalent flavoenzyme which catalyzes the oxidation of a variety of carbohydrates with high selectivity for cello- and maltooligosaccharides. Kinetic measurements suggested that this enzyme possesses an open carbohydrate-binding groove, which is mainly composed of two glucosyl-binding subsites. The encoding gene was subsequently cloned, and one intron was detected in the genomic DNA. Large amounts of active enzymes were expressed in Pichia pastoris , with a yield of 300 mg per liter medium. The protein was predicted to share structural homology with plant cytokinin dehydrogenase and related flavoproteins that share a conserved flavin adenine dinucleotide (FAD)-binding domain. The closest sequence matches are those of plant berberine bridge enzyme-like proteins, particularly the characteristic flavinylation site. Unexpectedly, mutation of the putative FAD-attaching residue, H70, to alanine, serine, cysteine, and tyrosine did not abolish the covalent FAD linkage and had little effect on the K _m . Instead, the variants displayed k _cat values that were 50- to 600-fold lower, indicating that H70 is crucial for efficient redox catalysis, perhaps through modulation of the oxidative power of the flavin.

  摘要 葡萄糖寡糖氧化酶 的葡萄糖寡糖氧化酶 中的葡萄糖低聚糖氧化酶进行了筛选，以确定其在低聚糖酸生产和碳水化合物检测中的潜在应用。该蛋白是一种独特的共价黄酮酶，可催化多种碳水化合物的氧化，对纤维寡糖和麦芽寡糖具有高选择性。动力学测量表明，这种酶具有一个开放的碳水化合物结合槽，主要由两个葡萄糖基结合亚位点组成。随后克隆了编码基因，并在基因组 DNA 中检测到一个内含子。大量活性酶在 Pichia pastoris 中表达了大量活性酶，每升培养基的产量为 300 毫克。据预测，该蛋白与植物细胞分裂素脱氢酶及相关黄素蛋白在结构上具有同源性，它们共享一个保守的黄素腺嘌呤二核苷酸（FAD）结合域。与之序列最接近的是植物小檗碱桥酶样蛋白，尤其是其特有的黄素化位点。出乎意料的是，将假定的 FAD 连接残基 H70 突变为丙氨酸、丝氨酸、半胱氨酸和酪氨酸并不能取消 FAD 的共价连接，而且对 FAD 的合成几乎没有影响。 K m .相反，显示的变量 k cat 值低 50 到 600 倍，这表明 H70 对高效氧化还原催化作用至关重要，也许是通过调节黄素的氧化能力实现的。
• Enzyme-Responsive Molecular Assembly System with Amylose-Primer Surfactants
  作者：Nobuyuki Morimoto、Naruhito Ogino、Tadashi Narita、Shinichi Kitamura、Kazunari Akiyoshi

  DOI：10.1021/ja065966a

  日期：2007.1.1

  The association of amylose-primer surfactants was controlled by changing the amphiphilicity with a chain-elongation reaction triggered by the addition of phosphorylase. By using this property, the micelle-to-vesicle transition of mixed lipid/primer systems can be controlled.
• Preparation of oligosaccharide aldonolactones and N-(2-aminoethyl)aldonamides
  作者：Winfried N. Emmerling、Beate Pfannemüller

  DOI：10.1016/s0008-6215(00)85912-1

  日期：1980.11
• Physical properties and packing states of molecular assemblies of synthetic glycolipids in aqueous dispersions
  作者：Shinji Takeoka、Keitaro Sou、Christoph Boettcher、Jürgen-Hinrich Fuhrhop、Eishun Tsuchida

  DOI：10.1039/a800289d

  日期：——

  Amidic glycolipids, 1,5-bis-O-alkyl-N-maltooligonoyl-L-glutamate (1), having various lengths of two hydrocarbon chains (carbon number, m: 14, 16, 18) and maltooligotose with (glucose unit, n: 3, 5, 7) and a N-glycosidic lipid, 1,5-bis-O-octadecyl-N-maltopentaonosyl-L-glutamate (2) have been synthesized. The assembling structures were analyzed by microscopic observation, such as negatively stained TEM, cryo-TEM, and AFM. The glycolipid 1a (m,n: 14,5) showed a fiber-like structure in all the observed temperatures, while 1b (16,5) showed a fiber-like structure when the hydrating temperature was above the gel-to-liquid crystalline phase transition temperature (Tc; 45°C) and a large disk-like structure when incubated below the Tc. The glycolipid 1c (18,5) took a large disk-like structure after hydration of the powder above the Tc. The glycolipids 1d (18,3) and 1e (18,7) showed a mixture of large disks and large vesicles and a mixture of small disks and micelles, respectively. The N-glycosidic lipid, 2, with no amide linkage made a vesicular structure only. The preparation procedure using high shear stress, such as extrusion and sonication, converted the large disk of 1c to smaller assemblies, such as small disk-, cone-, and granule-like assemblies, depending on the preparation conditions. The glycolipid molecules in the planer part of the disk were packed so tightly that molecular mobility was very low even above the Tc (58°C), and the reactivity of the saccharide chain against Concanavalin A was also very low, indicating that the high reactivity probably comes from the loose packing of saccharide chains around the edge part of the assemblies.

  合成了具有不同长度的两条碳氢链（碳数，m：14、16、18）和含有（葡萄糖单位，n：3、5、7）麦芽寡糖的酰胺糖脂--1,5-双-O-烷基-N-麦芽寡糖酰-L-谷氨酸（1），以及一种 N-糖苷脂--1,5-双-O-十八烷基-N-麦芽酮基-L-谷氨酸（2）。通过负染 TEM、冷冻 TEM 和原子力显微镜等显微镜观察分析了其组装结构。糖脂 1a（m,n：14,5）在所有观察温度下都呈现出纤维状结构，而糖脂 1b（16,5）在水合温度高于凝胶-液晶相转变温度（Tc；45°C）时呈现出纤维状结构，在低于 Tc 时则呈现出大圆盘状结构。糖脂 1c（18,5）在水合温度高于 Tc 时呈大圆盘状结构。糖脂 1d（18,3）和 1e（18,7）分别呈现出大圆盘和大囊泡的混合物以及小圆盘和胶束的混合物。没有酰胺连接的 N-糖苷脂质 2 只形成了囊泡结构。使用挤压和超声等高剪切应力的制备程序可将 1c 的大圆盘转化为较小的组装体，如小盘状、锥状和颗粒状组装体，具体取决于制备条件。圆盘平面部分的糖脂分子紧密堆积，即使在 Tc（58°C）以上，分子流动性也很低，糖链对康卡伐林 A 的反应活性也很低，这表明高反应活性可能来自于组装体边缘部分糖链的松散堆积。