麦芽七糖 | 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
• 中文名称: 麦芽七糖
• 英文名称: malto-heptaose
• 英文别名: maltoheptaose；O⁴-lin-Hexa[1α]4]-D-glucopyranosyl-D-glucose；Einecs 252-119-4；(2R,3R,4R,5R)-4-[(2R,3R,4R,5S,6R)-5-[(2R,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-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal
• CAS: 34620-78-5
• 化学式: C₄₂H₇₂O₃₆
• 分子量: 1153.01
• InChiKey: ZHZITDGOAFCURV-VVTKTIMZSA-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)：
  -15.8
• 重原子数：
  78
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  593
• 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：

  麦芽七糖 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 β-D-maltoheptaosyl azide
  参考文献：
  名称：

  Sweet Block Copolymer Nanoparticles: Preparation and Self-Assembly of Fully Oligosaccharide-Based Amphiphile

  摘要：

  The preparation of biocompatible nanocarriers that have potential applications in the cosmetic and health industries is highly desired. The self-assembly of amphiphilic block copolymers displaying biosourced polysaccharides at the surface is one of the most promising approaches. In the continuity of our works related to the preparation of "hybrid" amphiphilic oligosaccharide-based block copolymers, we present here the design of a new generation of self-assembled nanoparticles composed entirely of oligosaccharide-based amphiphilic block co-oligomers (BCO). These systems are defined by a covalent linkage of the two saccharidic blocks through their reducing end units, resulting in a sweet "head-to-head" connection. As an example, we have prepared and studied a BCO in which the hydrophilic part is composed of a free maltoheptaosyl derivative clicked to a hydrophobic part composed of a peracetylated maltoheptaosyl derivative. This amphiphilic BCO self-assembles to form spherical micelles in water with an average diameter of 30 nm. The efficient enzymatic hydrolysis of the maltoheptaose that constitutes the shell of the micelles was followed by light scattering and colorimetric methods.

  DOI：

  10.1021/bm3000138
• 作为产物：
  描述：

  β-环糊精 在 iron(III) chloride 、 乙酸酐 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 麦芽七糖
  参考文献：
  名称：

  Sweet Block Copolymer Nanoparticles: Preparation and Self-Assembly of Fully Oligosaccharide-Based Amphiphile

  摘要：

  The preparation of biocompatible nanocarriers that have potential applications in the cosmetic and health industries is highly desired. The self-assembly of amphiphilic block copolymers displaying biosourced polysaccharides at the surface is one of the most promising approaches. In the continuity of our works related to the preparation of "hybrid" amphiphilic oligosaccharide-based block copolymers, we present here the design of a new generation of self-assembled nanoparticles composed entirely of oligosaccharide-based amphiphilic block co-oligomers (BCO). These systems are defined by a covalent linkage of the two saccharidic blocks through their reducing end units, resulting in a sweet "head-to-head" connection. As an example, we have prepared and studied a BCO in which the hydrophilic part is composed of a free maltoheptaosyl derivative clicked to a hydrophobic part composed of a peracetylated maltoheptaosyl derivative. This amphiphilic BCO self-assembles to form spherical micelles in water with an average diameter of 30 nm. The efficient enzymatic hydrolysis of the maltoheptaose that constitutes the shell of the micelles was followed by light scattering and colorimetric methods.

  DOI：

  10.1021/bm3000138

文献信息

• Starch granule characterization by kinetic analysis of their stages during enzymic hydrolysis: 1H nuclear magnetic resonance studies
  作者：Anthony C. Dona、Guilhem Pages、Robert G. Gilbert、Philip W. Kuchel

  DOI：10.1016/j.carbpol.2010.10.042

  日期：2011.2.1

  Abstract 1H nuclear magnetic resonance (NMR) spectroscopy was used to study the kinetics of digestion of starch by two hydrolytic enzymes; specifically we studied the reactions of α-amylase from B. licheniformis (E.C. 3.2.1.1) and glucoamylase from Aspergillus niger (E.C. 3.2.1.3) with starch granules (early stages of digestion) and with oligosaccharides (a later stage). This was done to provide a

  摘要 利用1H核磁共振(NMR)光谱研究了两种水解酶消化淀粉的动力学；具体而言，我们研究了来自地衣芽孢杆菌 (EC 3.2.1.1) 的 α-淀粉酶和来自黑曲霉 (EC 3.2.1.3) 的葡糖淀粉酶与淀粉颗粒（消化的早期阶段）和寡糖（后期阶段）的反应。这样做是为了提供来自各种来源的淀粉颗粒的特征，关于从它们中释放葡萄糖的动力学。对于较小的寡糖，α-淀粉酶受其反应产物麦芽糖的抑制，而葡糖淀粉酶不受其主要产物葡萄糖的抑制。长达七个葡萄糖单位（麦芽七糖）的寡糖水解遵循米氏动力学。对于淀粉颗粒，实验证据表明，消化动力学在淀粉链水解后发生变化，淀粉链容易受到酶的攻击。快速消化阶段，包括对可接近的淀粉链的酶攻击，由经典的 Michaelis-Menten 动力学精确描述，而不考虑产物抑制。在缓慢消化阶段，速率显着下降；这被认为是由于葡萄糖间连接的不可接近性成为速率决定步骤。率显着下降；这被认为是由于
• Tagging saccharides for signal enhancement in mass spectrometric analysis
  作者：Yu-Ling Chang、Sylvain Kuo-Shiang Liao、Ying-Chu Chen、Wei-Ting Hung、Hui-Ming Yu、Wen-Bin Yang、Jim-Min Fang、Chung-Hsuan Chen、Yuan Chuan Lee

  DOI：10.1002/jms.1887

  日期：2011.3

  enhancer for maltoheptaose, GlcNAc oligomers and oligogalacturonic acids. In the MALDI‐TOF‐MS analysis using 2,5‐dihydroxybenzoic acid (2,5‐DHB) as the matrix, the GalA4–BK and GalA5–BK conjugates prepared by reductive amination showed the detection limit at 0.1 fmol, i.e. ∼800‐fold enhancement over the unmodified pentagalacturonic acids. The remarkable MS enhancement was attributable to the synergistic

  MALDI-MS可对大型生物分子（例如蛋白质和核酸）进行快速灵敏的分析。但是，寡糖和多糖在质谱分析中灵敏度较低，部分原因是它们具有中性和亲水性，导致电离效率低。在这项研究中，通过还原末端的适当标签修饰了醛糖，氨基醛糖，醛糖醛酸和α-酮酸这四种低聚糖，以提高其电离效率。缓激肽（BK）是一种血管活性的九肽（RPPGFSPFR），含有两个精氨酸和两个苯丙氨酸残基，被证明是麦芽七糖，GlcNAc低聚物和低聚半乳糖醛酸的出色MS信号增强剂。在以2,5-二羟基苯甲酸（2,5-DHB）为基质的MALDI-TOF-MS分析中，还原胺化制得的GalA4-BK和GalA5-BK结合物的检出限为0.1 fmol，即比未修饰的五内酯酸高约800倍。MS的显着增强归因于碱性精氨酸残基对高质子亲和力和疏水性苯基丙氨酸残基对电离的协同作用。四肽GFGR（OMe）和精氨酸连接的苯二胺（H因此2 N）2 Ph-R（OMe）
• PERMETHYLATION OF OLIGOSACCHARIDES
  申请人：Kang Pilsoo

  公开号：US20110015386A1

  公开（公告）日：2011-01-20

  A solid-phase permethylation procedure is described. For example, solid-phase permethylation can be utilized to prepare permethylated linear and branched, neutral and sialylated oligosaccharides, which can be analyzed by MALDI-MS.

  描述了一种固相甲基化过程。例如，固相甲基化可以用于制备甲基化的线性和分支的中性和唾液酸化寡糖，这些寡糖可以通过MALDI-MS进行分析。
• Expanding Glycomic Investigations through Thiol-Derivatized Glycans
  作者：Robert D. Hurst、Angel Nieves、Matthew Brichacek

  DOI：10.3390/molecules28041956

  日期：——

  convenient, shelf-stable thiol directly onto the desired free glycans with purification advantages and direct modification with efficient reactions through alkenes, halides, epoxides, disulfides, and carboxylates in yields of 49% to 93%. Subsequently, a thiol-selective modification of the BSA protein was used to generate a neoglycoprotein with a bifunctional PEG-maleimide linker. To further illustrate the

  合成了一种新型聚糖助剂 N-(2-硫乙基)-2-氨基苯甲酰胺 (TEAB) 并评估了其实用性。通过使用水稳定试剂 2-甲基吡啶硼烷复合物进行还原胺化，将辅助剂与聚糖缀合。通过反相色谱纯化后，聚糖产物（范围为 1 至 7 个连接的己糖）均以 60% 至 90% 的产率分离。这种新型缀合物将方便的、货架稳定的硫醇直接引入到所需的游离聚糖上，具有纯化优势，并通过烯烃、卤化物、环氧化物、二硫化物和羧酸盐进行有效反应进行直接修饰，产率为 49% 至 93%。随后，对 BSA 蛋白进行硫醇选择性修饰，生成具有双功能 PEG-马来酰亚胺接头的新糖蛋白。为了进一步说明硫醇基序的实用性，含硫醇支持物的 2-硫代吡啶活化促进了标记聚糖的共价色谱纯化，收率高达 63%。最后，通过 FITC 标记的刀豆球蛋白 A 结合探索和验证了光印刷微阵列中实施概念的初步证明。总之，所产生的硫醇功能化聚糖极大地扩展了可以用聚糖
• Controlled synthesis of amphiphilic rod-coil biodegradable maltoheptaose-graft-poly(ɛ-caprolactone) copolymers
  作者：Xiongying Qiu、Caiqi Wang、Juan Shen、Mingwei Jiang

  DOI：10.1016/j.carbpol.2010.10.034

  日期：2011.2.1

  The controlled synthesis of novel amphiphilic biodegradable maltoheptaose-graft-poly(epsilon-caprolactone) copolymers was achieved through a three-step method. The first step consisted of partial silylation of the maltoheptaose hydroxyl groups. This protection step was followed by ring-opening polymerization of epsilon-caprolactone initiated from the remaining OH functional group of the partially silylated oligosaccharide. The third step involved the deprotection of the silylether group under mild conditions. The effects of varying the experimental conditions on grafting efficiency and graft length were investigated to ensure controlled polymerization of epsilon-caprolactone. The protection and deprotection of the TMS group during the entire procedure were carefully monitored with Fourier transform infrared (FTIR) and H-1 NMR. The final graft copolymers were characterized by FTIR, H-1 NMR, gel permeation chromatography (GPC), and differential scanning calorimetry (DSC). (C) 2010 Elsevier Ltd. All rights reserved.