D-(+)-纤维四糖 | 38819-01-1

• 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: D-(+)-纤维四糖
• 中文别名: 纤维四糖
• 英文名称: cellotetraose
• 英文别名: cellotetrose；O⁴-[O⁴-(O⁴-β-D-Glucopyranosyl-β-D-glucopyranosyl)-β-D-glucopyranosyl]-D-glucose；(2R,3R,4R,5R)-4-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,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-2,3,5,6-tetrahydroxyhexanal
• CAS: 38819-01-1
• 化学式: C₂₄H₄₂O₂₁
• 分子量: 666.585
• InChiKey: UYQJCPNSAVWAFU-ZEUIETHYSA-N

物化性质

• 沸点：
  597.68°C (rough estimate)
• 密度：
  1.3922 (rough estimate)
• 溶解度：
  H2O：50 mg/mL，澄清，无色
• LogP：
  -8.281 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  -9.3
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  356
• 氢给体数：
  14
• 氢受体数：
  21

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  29400090

制备方法与用途

概述

低聚糖集营养、保健、食疗于一体，广泛应用于食品、保健品、饮料、医药、饲料添加剂等领域，被誉为“未来型”新一代功效食品。目前产量最大、应用最广的低聚糖主要来源于淀粉，通常称为麦芽低聚糖。麦芽四糖是由 α-1，4 糖苷键连接的葡萄糖四聚体，是一种新型的麦芽低聚糖。

功能特性

麦芽四糖（G4，Maltotetraose）是由α-1, 4糖苷键连接的葡萄糖四聚体，一般是由麦芽四糖淀粉酶水解淀粉而来，属于低聚麦芽糖中的直链低聚麦芽糖，集营养、保健、食疗等功能于一体，被誉为最有希望的低聚麦芽糖。
麦芽四糖的甜度仅为蔗糖的20％，但粘度为蔗糖的5倍，是一种极好的食品添加剂。麦芽四糖对氨基酸引起的褐变反应（也称为美拉德反应）具有很高的稳定性，并且耐酸和耐热。另外，麦芽四糖还具有防止食品中蛋白质变性及保持速冻食品新鲜度等功能。同时，它还是很好的保健品，可作为“功能性食品”的原料，主要添加到家禽、家畜、鱼等饲料中，还可使用于养蜂、养蚕等。

主要性质

麦芽四糖外观呈无色、透明、粘稠状液体，口感微甜、无任何不良异味，也无可见杂质。它具有保湿性好、吸湿性低、增稠作用强，有一定的耐酸和耐热性，冰点作用小，易形成光泽皮膜等特点，因此具有良好的使用性。另外，麦芽四糖还具有防止食品中蛋白质变性及保持速冻食品新鲜度等功能。

应用

麦芽四糖由于其良好的流动性、无色、无异臭味、微甜等特点，在食品行业被广泛应用，并且用量比例很高时，也不会掩盖产品原有食品的风味和香味，是一种优良的添加剂。麦芽四糖易溶于水，黏性适度，增稠性、胶黏性、抑制糖结晶和稳定泡沫的效果好，具有优良的乳化性能，有促进产品成型和调整产品组织结构的作用，可用于糖果、糕点、饮料、冷饮中，能防止晶体析出、抑制淀粉老化、增加粘稠感、提高食品的感官品质。

功效与作用

1）优良的食品添加剂：麦芽四糖由于其良好的流动性、无色、无异臭味、微甜等特点，在食品行业被广泛应用，是一种优良的添加剂。麦芽四糖易溶于水，黏性适度，增稠性、胶黏性、抑制糖结晶和稳定泡沫的效果好，具有优良的乳化性能，有促进产品成型和调整产品组织结构的作用，可用于糖果、糕点、饮料、冷饮中，能防止晶体析出、抑制淀粉老化、增加粘稠感、提高食品的感官品质。
2）功能性食品：麦芽四糖具有较好的耐酸盐和耐热性，并且不易褐变，在人体内的消化吸收非常好，可作为儿童病人及运动员的食品原料。人体长期食用，能有效抑制肠道中产气腐败菌和胡萝卜软腐欧文氏病原菌的增殖，具有净化肠道、增进健康的作用。因此，近年来麦芽四糖在食品行业中得到广泛的应用，是理想的食品基础原料。
3）作为经肠营养剂：经肠营养剂是专门为消化吸收机能低下和低营养状态的人群设计的一种营养品。该营养物质是以经口、经管营养为主的营养剂，以补助营养为目的，可刺激食欲和调节胃肠道功能，并且安全易行，因此受到广泛的应用。然而经肠营养剂中的糖类以前多采用葡萄糖、蔗糖、麦芽糖等单糖或双糖，但由于这些糖类使用时渗透压很高，很容易引起渗透压性腹泻，所以都会同时加入调节渗透压的糊精。研究发现，麦芽四糖由于其分支结构少，并且属于直链状的低聚糖，低渗透压，能够以高效率分解、代谢，所以可以作为营养剂有效的糖类和能量来源。

制备

1.单酶法制备麦芽四糖

主要采用麦芽四糖淀粉酶分解淀粉得到。由于该酶具有的独特分子结构性质，淀粉需经预处理，使其DE 值控制在 8~12，添加麦芽四糖酶量应控制在 0。02%，最适反应温度为 58 ℃，最适反应 pH 值为 6。8~7。0，最适反应时间 6~7 h，得麦芽四糖粗水解液。粗水解液再经灭酶、冷却澄清、过滤、真空浓缩、喷雾干燥，成固体成品。该方法简单易行，且成本不高，被广泛应用。

2.普鲁兰酶协同作用制备麦芽四糖

普鲁兰酶是一种支链淀粉酶，它对支链淀粉和糖原等支点的 α-1，6 糖苷键具有很强的水解作用，生产低聚异麦芽糖时，大多以玉米和木薯淀粉为原料，淀粉经液化、糖化或再转苷，再经过滤、离子交换等处理得到具有一定浓度的糖浆或糖粉。利用酶法生产麦芽四糖，应适当加入普鲁兰酶作为协同酶。因为加入普鲁兰酶之后大多数淀粉糖的过滤速度都减慢了，但糖浆透射比增大，有利于提高糖的品质。

化学性质

白色结晶粉末，可溶于甲醇、乙醇、DMSO等有机溶剂，来源于蜂蜜。

用途

用于含量测定/鉴定/药理实验等

反应信息

• 作为反应物：
  描述：

  D-(+)-纤维四糖 在 Cellulosimicrobium cellulans strain 21 GH1 β-glucosidase CcBgl1B, recombinant, molecular weight: 57 kDa 、 水 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.34h， 生成 D-纤维二糖
  参考文献：
  名称：

  Cloning, expression and biochemical characterization of a GH1 β-glucosidase from Cellulosimicrobium cellulans

  摘要：

  beta-Glucosidase plays an important role in the degradation of cellulose. In this study, a novel -glucosidase ccbgl1b gene for a glycosyl hydrolase (GH) family 1 enzyme was cloned from the genome of Cellulosimicrobium cellulans and expressed in Escherichia coli BL21 cells. The sequence contained an open reading frame of 1494bp, encoded a polypeptide of 497amino acid residues. The recombinant protein CcBgl1B was purified by Ni sepharose fastflow affinity chromatography and had a molecular weight of 57kDa, as judged by SDS-PAGE. The optimum -glucosidase activity was observed at 55 degrees C and pH 6.0. Recombinant CcBgl1B was found to be most active against aryl-glycosides p-nitrophenyl--D-glucopyranoside (pNPGlc), followed by p-nitrophenyl--D-galactopyranoside (pNPGal). Using disaccharides as substrates, the enzyme efficiently cleaved -linked glucosyl-disaccharides, including sophorose (-1,2-), laminaribiose (-1,3-) and cellobiose (-1,4-). In addition, a range of cello-oligosaccharides including cellotriose, cellotetraose and cellopentaose were hydrolysed by CcBgl1B to produce glucose. The interaction mode between the enzyme and the substrates driving the reaction was modelled using a molecular docking approach. Understanding how the GH1 enzyme CcBgl1B from C. cellulans works, particularly its activity against cello-oligosaccharides, would be potentially useful for biotechnological applications of cellulose degradation.

  DOI：

  10.1080/10242422.2017.1395415
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 甲醇 、 sodium methylate 作用下， 生成 D-(+)-纤维四糖
  参考文献：
  名称：

  The Polymer-homologous Series of Oligosaccharides from Cellulose¹

  摘要：

  DOI：

  10.1021/ja01141a032

文献信息

• Properties of a Metagenome-Derived β-Glucosidase from the Contents of Rabbit Cecum
  作者：Yi FENG、Cheng-Jie DUAN、Li LIU、Ji-Liang TANG、Jia-Xun FENG

  DOI：10.1271/bbb.80664

  日期：2009.7.23

  In this study, a previously cloned β-glucosidase gene, umbgl3B, was heterologously expressed in Escherichia coli, and the biochemical properties of the purified enzyme were characterized. The recombinant enzyme was stable over a wide range of pH values (5.0–9.0) and below 30 °C. It displayed optimum enzymatic activity at pH 6.5 at 40 °C, under condition similar to that in the rabbit cecum, suggesting an active role of the native enzyme in vivo. The recombinant β-glucosidase Umbgl3B showed high activity to aryl β-d-glucosides and low activity to cellooligosaccharides, with a polymerization degree of less than 5. The enzyme had no activity toward long cellooligosaccharides or polysaccharides. The aspartic acid residue, D772, of the wild-type Umbgl3B was predicted as a nucleophile. Mutant D772A was constructed. It showed less than 1/10,000 activity of the wild-type enzyme, but had the same properties, suggesting that residue D772 plays a key role in the enzyme’s activity.

  在本研究中，之前克隆的β-葡萄糖苷酶基因umbgl3B在大肠杆菌中进行异源表达，并对纯化酶的生化性质进行了表征。重组酶在pH值范围（5.0–9.0）和30°C以下稳定。它在pH 6.5和40°C的条件下显示出最佳酶活性，这与兔盲肠中的环境条件相似，表明该酶在体内具有活跃作用。重组β-葡萄糖苷酶Umbgl3B对芳基β-D-葡萄糖苷表现出高活性，而对聚糖寡糖（聚合度小于5）则活性较低。该酶对长链聚糖或多糖没有活性。野生型Umbgl3B的天冬氨酸残基D772被预测为亲核试剂。构建了突变体D772A。它的活性不到野生型酶的1/10,000，但具有相同的性质，表明残基D772在酶的活性中发挥了关键作用。
• Effects of active site cleft residues on oligosaccharide binding, hydrolysis, and glycosynthase activities of rice BGlu1 and its mutants
  作者：Salila Pengthaisong、James R. Ketudat Cairns

  DOI：10.1002/pro.2556

  日期：2014.12

  mode in BGlu1 E176Q and E386G, but in a different mode in the BGlu1 E386G/Y341A variant, in which glucosyl residue 4 (Glc4) interacts with Q187 instead of the eliminated phenolic group of Y341. Here, we found that the Q187A mutation has little effect on BGlu1 cellooligosaccharide hydrolysis activity or oligosaccharide binding in BGlu1 E176Q, and only slight effects on BGlu1 E386G glycosynthase activity

  稻米BGlu1（Os3BGlu7）是一种糖苷水解酶1β-葡萄糖苷酶，随着聚合度（DP）从2增加到6，水解纤维素寡糖的效率提高，这表明有6个用于糖基残基结合的亚位点。在纤维寡糖复合物的X射线晶体结构及其E176Q酸碱和E386G亲核突变体中，鉴定出五个亚位点。X射线晶体结构表明，纤维四糖在BGlu1 E176Q和E386G中以相似的方式结合，但在BGlu1 E386G / Y341A变异体中以不同的方式结合，其中葡糖基残基4（Glc4）与Q187相互作用而不是被消除的酚基Y341。在这里，我们发现Q187A突变对BGlu1纤维寡糖水解活性或BGlu1 E176Q中寡糖结合的影响很小，对BGlu1 E386G糖合酶活性的影响很小。X射线晶体结构显示，纤维四糖在BGlu1 E176Q / Y341A中的不同位置结合，在其中它与R178和W337直接相互作用，而Q187A突变对纤维四糖的结合几乎没
• Identification of Rice β-Glucosidase with High Hydrolytic Activity towards Salicylic Acid β-<scp>D</scp>-Glucoside
  作者：Nami HIMENO、Wataru SABURI、Shinji WAKUTA、Ryosuke TAKEDA、Hideyuki MATSUURA、Kensuke NABETA、Sompong SANSENYA、James R. KETUDAT CAIRNS、Haruhide MORI、Ryozo IMAI、Hirokazu MATSUI

  DOI：10.1271/bbb.120889

  日期：2013.5.23

  beta-Glucosidases (EC 3.2.1.21) split beta-glucosidic linkages at the non-reducing end of glucosides and oligosaccharides to release beta-D-glucose. One of the important functions of plant beta-glucosidase is deglucosylation of inactive glucosides of phytohormones to regulate levels of active hormones. Tuberonic acid is a jasmonate-related compound that shows tuber-inducing activity in the potato. We have identified two enzymes, OsTAGG1 and OsTAGG2, that have hydrolytic activity towards tuberonic acid beta-D-glucoside in rice (Oryza sativa L.). The expression of OsTAGG2 is upregulated by wounding and by methyl jasmonate, suggesting that this isozyme is involved in responses to biotic stresses and wounding, but the physiological substrate of OsTAGG2 remains ambiguous. In this study, we produced recombinant OsTAGG2 in Pichia pastoris (rOsTAGG2P), and investigated its substrate specificity in detail. From 1 L of culture medium, 2.1 mg of purified recombinant enzyme was obtained by ammonium sulfate precipitation and Ni-chelating column chromatography. The specific activity of rOsTAGG2P (182 U/mg) was close to that of the native enzyme (171 U/mg), unlike recombinant OsTAGG2 produced in Escherichia coli, which had approximately 3-fold lower specific activity than the native enzyme. The optimum pH and temperature for rOsTAGG2P were pH 3.4 and 60 degrees C. After pH and heat treatments, the enzyme retained its original activity in a pH range of 3.4-9.8 and below 55 degrees C. Native OsTAGG2 and rOsTAGG2P showed 4.5-4.7-fold higher activities towards salicylic acid beta-D-glucoside, an inactive storage-form of salicylic acid, than towards tuberonic acid beta-D-glucoside (TAG), although OsTAGG2 was originally isolated from rice based on TAG-hydrolytic activity.
• Enzymatic synthesis of cellulose II-like substance via cellulolytic enzyme-mediated transglycosylation in an aqueous medium
  作者：Takeshi Hattori、Makoto Ogata、Yumiko Kameshima、Kazuhide Totani、Mitsuru Nikaido、Takashi Nakamura、Hiroyuki Koshino、Taichi Usui

  DOI：10.1016/j.carres.2012.03.018

  日期：2012.5

  The enzymatic synthesis of cellulose-like substance via a non-biosynthetic pathway has been achieved by transglycosylation in an aqueous system of the corresponding substrate, cellotriose for cellulolytic enzyme endo-acting endoglucanase I (EG I) from Hypocrea jecorina. A significant amount of water-insoluble product precipitated out from the reaction system. MALDI-TOF mass analysis showed that the resulting precipitate had a degree of polymerization (DP) of up to 16 from cellotriose. Solid-state C-13 NMR spectrum of the resulting water-insoluble product revealed that all carbon resonance lines were assigned to two kinds of anhydroglucose residues in the corresponding structure of cellulose II. X-ray diffraction (XRD) measurement as well as C-13 NMR analysis showed that the crystal structure corresponds to cellulose II with a high degree of crystallinity. We propose the multiple oligomers form highly crystalline cellulose II as a result of self-assembly via oligomer-oligomer interaction when they precipitate. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.
• Walker; Wright, Archives of Biochemistry, 1957, vol. 69, p. 362,366
  作者：Walker、Wright

  DOI：——

  日期：——

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