maltoheptaose | 34620-78-5

• 物质功能分类: 生物化工 - 糖类化合物 - 寡糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: maltoheptaose
• 英文别名: 2-[6-[6-[6-[6-[4,5-Dihydroxy-2-(hydroxymethyl)-6-[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol；(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 34620-78-5
• 化学式: C₄₂H₇₂O₃₆
• 分子量: 1153.01
• InChiKey: BNABBHGYYMZMOA-QJBBZCPBSA-N

物化性质

• 熔点：
  220-222°C
• 沸点：
  1492.7±65.0 °C(Predicted)
• 密度：
  1.85±0.1 g/cm3(Predicted)
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -15.5
• 重原子数：
  78
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  585
• 氢给体数：
  23
• 氢受体数：
  36

安全信息

• WGK Germany：
  3
• 海关编码：
  29400090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

生物活性

Maltoheptaose hydrate 是磷酸化酶 B (phosphorylase B) 的活化剂，可用于制备 2-磷酸庚糖。这种物质是一种含有七个葡萄糖单元的麦芽低聚糖。

靶点

磷酸化酶 B

用途

适用于含量测定、鉴定以及药理实验等。

反应信息

• 作为反应物：
  描述：

  maltoheptaose 在 sodium azide 、 CIP 、 N,N-二异丙基乙胺 作用下， 以 水 为溶剂， 以49%的产率得到β-D-maltoheptaosyl azide
  参考文献：
  名称：

  未保护的1,4个连接葡聚糖的区域选择性氧化†

  摘要：

  钯催化的醇氧化可以对未保护的1,4连接的葡聚糖进行化学和区域选择性修饰。1,7连接的葡聚糖直至7-mer的两步双功能化证明了这一点。引入端基叠氮化物后，对末端C3-OH官能团进行高度区域选择性的单氧化。如4-草酸巴豆酸酯互变异构酶的半胱氨酸突变体与生物素的缀合所证明的，所得的正交双官能化寡糖是PEG-间隔子的可行替代物。

  DOI：

  10.1039/c6ob00608f
• 作为产物：
  描述：

  β-环糊精 在 iron(III) chloride 、 sodium methylate 作用下， 以 甲醇 、 乙酸酐 为溶剂， 生成 maltoheptaose
  参考文献：
  名称：

  Entirely oligosaccharide-based supramolecular amphiphiles constructed via host–guest interactions as efficient drug delivery platforms

  摘要：

  通过ferrocene-终止的乙酰化七糖（Fc-AcMH）和β-环糊精终止的四臂星状七糖（MH4-β-CD）之间的宿主-客体相互作用构建了完全基于寡糖的超分子两性分子。

  DOI：

  10.1039/c7cc06553a

文献信息

• Synthesis of sulfated alkyl malto- and laminara-oligosaccharides with potent inhibitory effects on AIDS virus infection
  作者：Kaname Katsuraya、Naoya Ikushima、Nahoko Takahashi、Tadao Shoji、Hideki Nakashima、Naoki Yamamoto、Takashi Yoshida、Toshiyuki Uryu

  DOI：10.1016/0008-6215(94)80021-9

  日期：1994.7

  A series of sulfated alkyl oligosaccharides, including a sulfate dodecyl laminarapentaoside and a sulfated octadecyl maltohexaoside with potent anti-human immunodeficiency virus (HIV) activity, has been synthesized. An alkyl oligosaccharide in which a long alkyl group is bonded to the reducing end of the oligosaccharide was first synthesized in high yield. Peracetylated oligosaccharides reacted with

  合成了一系列硫酸化的烷基寡糖，包括具有有效抗人免疫缺陷病毒（HIV）活性的硫酸化十二烷基十二烷基戊糖苷和硫酸化十八烷基麦芽六糖苷。首先以高收率合成了其中长烷基键合至寡糖的还原端的烷基寡糖。过乙酰化的低聚糖与路易斯酸作为催化剂的脂肪族醇（如1-癸基醇和1-十二烷基醇）反应。如在α和β过乙酰化的糖苷的糖基化中一样，β异头异构体仅反应，在高温下用乙酸钠-乙酸酐进行乙酰化以使β异头异构体的比例最大化。
• Enzymatic synthesis and characterization of maltoheptaose-based sugar esters
  作者：Phu Cuong Nguyen、My Tuyen Thi Nguyen、Chang-Kyu Lee、Il-Nam Oh、Jae-Han Kim、Soon-Taek Hong、Jong-Tae Park

  DOI：10.1016/j.carbpol.2019.04.079

  日期：2019.8

  the ester bond in the G7 was located at C-6 of the glucose at the reducing end. The G7-PA monoester showed the melting temperature at 56.3 °C that was 6.5 °C lower than that of the free PA and exhibited a different endothermic pattern from the free G7. The G7-PA monoester exhibited excellent emulsifier potential with more even droplet size distribution compared with the commercial sucrose esters for

  在这项研究中，基于麦芽七糖（G7）的糖酯是使用商业脂肪酶由麦芽七糖和脂肪酸（C10–C16）合成的。除了二甲基亚砜（DMSO； 76.4％，w / v）外，G7在有机溶剂中的溶解度有限。在脂肪酸中，棕榈酸（PA）是形成G7基酯的最佳底物。G7-PA酯仅在10％DMSO的叔丁醇中成功合成为单酯结构，转化率为22％。纯化的单酯产物的NMR和酶促分析表明，G7中的酯键位于还原端的葡萄糖的C-6处。G7-PA单酯显示的熔融温度为56.3°C，比游离PA的熔融温度低6.5°C，并且表现出与游离G7不同的吸热模式。
• Purification, Characterization, and Subsite Affinities of<i>Thermoactinomyces vulgaris</i>R-47 Maltooligosaccharide-metabolizing Enzyme Homologous to Glucoamylases
  作者：Kazuhiro ICHIKAWA、Takashi TONOZUKA、Rie UOTSU-TOMITA、Hiromi AKEBOSHI、Atsushi NISHIKAWA、Yoshiyuki SAKANO

  DOI：10.1271/bbb.68.413

  日期：2004.1

  A maltooligosaccharide-metabolizing enzyme from Thermoactinomyces vulgaris R-47 (TGA) homologous to glucoamylases does not degrade starch efficiently unlike most glucoamylases such as fungal glucoamylases (Uotsu-Tomita et al., Appl. Microbiol. Biotechnol., 56, 465–473 (2001)). In this study, we purified and characterized TGA, and determined the subsite affinities of the enzyme. The optimal pH and temperature of the enzyme are 6.8 and 60°C, respectively. Activity assays with 0.4% substrate showed that TGA was most active against maltotriose, but did not prefer soluble starch. Kinetic analysis using maltooligosaccharides ranging from maltose to maltoheptaose revealed that TGA has high catalytic efficiency for maltotriose and maltose. Based on the kinetics, subsite affinities were determined. The A1+A2 value of this enzyme was highly positive whereas A4–A6 values were negative and little affinity was detected at subsites 3 and 7. Thus, the subsite structure of TGA is different from that of any other GA. The results indicate that TGA is a metabolizing enzyme specific for small maltooligosaccharides.

  来自热活性放线菌（Thermoactinomyces vulgaris R-47，简称 TGA）的一个代谢小麦糊精酶与葡萄糖淀粉酶同源，但其降解淀粉的效率不如大多数葡萄糖淀粉酶，例如真菌葡萄糖淀粉酶（Uotsu-Tomita 等，应用微生物和生物技术，56，465–473（2001））。在这项研究中，我们纯化并表征了 TGA，并确定了该酶的亚位点亲和力。该酶的最佳 pH 值和温度分别为 6.8 和 60°C。0.4% 底物的活性测定表明，TGA 对麦三糖的活性最高，但对可溶性淀粉并不偏好。使用从麦芽糖到麦七糖的麦糊精进行的动力学分析显示，TGA 对麦三糖和麦芽糖具有很高的催化效率。基于动力学，确定了亚位点亲和力。该酶的 A1+A2 值高度正值，而 A4–A6 值为负值，在亚位点 3 和 7 上几乎没有检测到亲和力。因此，TGA 的亚位点结构与任何其他葡萄糖淀粉酶不同。结果表明，TGA 是一种特定于小麦糊精的代谢酶。
• Purification and characterization of a chloride ion-dependent α-glucosidase from the midgut gland of Japanese scallop (<i>Patinopecten yessoensis</i>)
  作者：Yasushi Masuda、Masayuki Okuyama、Takahisa Iizuka、Hiroyuki Nakai、Wataru Saburi、Taro Fukukawa、Janjira Maneesan、Takayoshi Tagami、Tetsushi Naraoka、Haruhide Mori、Atsuo Kimura

  DOI：10.1080/09168451.2015.1116926

  日期：2016.3.3

  Marine glycoside hydrolases hold enormous potential due to their habitat-related characteristics such as salt tolerance, barophilicity, and cold tolerance. We purified an α-glucosidase (PYG) from the midgut gland of the Japanese scallop (Patinopecten yessoensis) and found that this enzyme has unique characteristics. The use of acarbose affinity chromatography during the purification was particularly effective, increasing the specific activity 570-fold. PYG is an interesting chloride ion-dependent enzyme. Chloride ion causes distinctive changes in its enzymatic properties, increasing its hydrolysis rate, changing the pH profile of its enzyme activity, shifting the range of its pH stability to the alkaline region, and raising its optimal temperature from 37 to 55 °C. Furthermore, chloride ion altered PYG’s substrate specificity. PYG exhibited the highest Vmax/Km value toward maltooctaose in the absence of chloride ion and toward maltotriose in the presence of chloride ion.

  摘要 海洋中的糖苷水解酶由于其耐盐性、耐压性和耐寒性等栖息地相关特性具有巨大潜力。我们从日本扇贝（Patinopecten yessoensis）的中肠腺中纯化出一种α-葡萄糖苷酶（PYG），发现这种酶具有独特的特性。在纯化过程中使用阿卡波糖亲和色谱特别有效，将特异活性提高了570倍。PYG是一种有趣的氯离子依赖性酶。氯离子导致其酶的性质发生显著变化，增加了其水解速率，改变了其酶活性的pH特性，将其pH稳定范围转移到碱性区域，并将其最适温度从37摄氏度提高到55摄氏度。此外，氯离子改变了PYG的底物特异性。在无氯离子存在时，PYG对马尔托八糖表现出最高的Vmax/Km值，在氯离子存在时对麦芽三糖表现出最高的Vmax/Km值。
• Purification and characterization of an α-glucosidase from germinating millet seeds
  作者：Yoshiki Yamasaki、Mikio Fujimoto、Junji Kariya、Haruyoshi Konno

  DOI：10.1016/j.phytochem.2005.02.024

  日期：2005.4

  4-fold lower than that for maltose. The enzyme preferably hydrolyzed amylopectin in starch, but also readily hydrolyzed nigerose, which has an α-1,3-glucosidic linkage and exists as an abnormal linkage in the structure of starch. In particular, the enzyme readily hydrolyzed millet starch from germinating seeds that had been degraded to some extent.

  摘要 α-葡萄糖苷酶（α-d-葡萄糖苷葡萄糖水解酶，EC 3.2.1.20）通过硫酸铵分馏、CM-cellulofine/Fractogel EMD SO 3 色谱法从发芽的小米（Panicum miliaceum L.）种子中分离出来。 Sephacryl S-200 HR 和 TSK 凝胶 Phenyl-5 PW，以及制备等电聚焦。该酶通过 SDS-PAGE 是同质的。根据其在 SDS-PAGE 中的迁移率估计该酶的分子量为 86,000，根据 TSKgel super SW 3000 的凝胶过滤估计为 80,000，这表明它由单个单元组成。该酶的等电点为8.3。该酶容易水解麦芽糖、麦芽低聚糖和 α-1,4-葡聚糖，但水解多糖的速度比麦芽糖快。K m 值随着底物分子量的增加而降低。麦芽七糖的值比麦芽糖的值低约 4 倍。该酶优选水解淀粉中的支链淀粉，但也容易水解具有α-1,3-糖苷键且在