nigerose | 2495-70-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: nigerose
• 英文别名: 3-O-α-D-glucopyranosyl-D-glucose；(3R,4S,5R,6R)-6-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2,3,5-triol
• CAS: 2495-70-7
• 化学式: C₁₂H₂₂O₁₁
• mdl: MFCD00057489
• 分子量: 342.3
• InChiKey: QIGJYVCQYDKYDW-NSYYTRPSSA-N

物化性质

• 沸点：
  690.5±55.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  nigerose 在 wild-type glycoside hydrolase LlGH₃₁_u1 from Lactococcuslactis subsp. cremoris MG₁₃₆₃ 作用下， 以 aq. phosphate buffer 为溶剂， 反应 1.0h， 生成 D-葡萄糖
  参考文献：
  名称：

  细菌 GH31 α-1,3-葡萄糖苷酶对黑寡糖的严格特异性的结构基础

  摘要：

  碳水化合物活性酶参与碳水化合物的降解、生物合成和修饰，并随着碳水化合物的多样性而变化。糖苷水解酶 (GH) 家族 31 是最多样化的碳水化合物活性酶家族之一，包含作用于 α-糖苷的各种酶。然而，一些 GH31 基团的功能仍然未知，因为它们的酶活性难以估计，因为特征成员和未特征成员之间的氨基酸序列相似性低。在这里，我们进行了系统发育分析，发现了一个与报道的 GH31 酶具有低序列相似性的蛋白质簇 (GH31_u1)。在这个集群中，我们发现来自乳酸乳球菌的 GH31_u1 蛋白(LlGH31_u1) 及其真菌同系物表现出对黑糖 [α-D-Glc p -(1→3)-D-Glc] 的水解活性。k猫/ K米_LlGH31_u1 对曲二糖和麦芽糖的值分别是对黑糖的 13% 和 2.1%，表明 LlGH31_u1 对黑糖的 α-1,3 键的特异性高于其他表征的 GH31 酶，包括真核酶。此外，使用 X 射线晶体学和低温电子显微镜确定的

  DOI：

  10.1016/j.jbc.2022.101827
• 作为产物：
  描述：

  3-O-苄基-1,2:5,6-O-双异丙叉-α-D-呋喃葡萄糖 在 吡啶 、 palladium on activated charcoal 、 4 A molecular sieve 、 Amberlite IR-120 (H⁽¹⁺⁾) 、 四丁基溴化铵 、 氢气 、 sodium methylate 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 copper(ll) bromide 作用下， 以 甲醇 、 乙二醇甲醚 、 水 为溶剂， 25.0~80.0 ℃ 、101.33 kPa 条件下， 反应 8.33h， 生成 nigerose
  参考文献：
  名称：

  Synthesis of nigero-oligosaccharides

  摘要：

  Nigerose [alpha-D-Glcp-(1 --> 3)-D-Glcp], nigerotriose, nigerotetraose, and nigeropentaose have been synthesized by chain elongation starting at the reducing end, from the corresponding octa-, undeca-, tetradeca-, and heptadeca-beta-D-acetates, respectively, via thioglycoside-mediated 1,2-cis coupling, using 1,2,4,6-tetra-O-acetyl-beta-D-glucopyranose as the glucosyl acceptor and methyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-glucopyranoside, methyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside, and methyl O-(2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl)-(1 --> 3)-2,4,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside as the donors.

  DOI：

  10.1016/0008-6215(92)84098-d

文献信息

• 1H-Nuclear magnetic resonance spectroscopy of reducing-residue anomeric protons of pertrifluoroacetylated carbohydrates
  作者：Steven T. Summerfelt、Etienne J.-M. Selosse、Peter J. Reilly、Walter S. Trahanovsky

  DOI：10.1016/0008-6215(90)80014-t

  日期：1990.8

  from the same carbohydrates when they were free or derivatized with other groups. Neither the location of anomeric proton peaks relative to each other nor the degree of spin-spin coupling between H-1 and H-2 varied greatly with type of derivatization. Spin-spin coupling, however, decreased for some beta-pyranose forms of xylobiose and the three trisaccharides. In all examples except some where H-2 was

  八个单糖（L-阿拉伯糖苷，L-岩藻糖，D-半乳糖，D-葡萄糖，D-lyxose，D-甘露糖，L-鼠李糖和D-木糖），八个二糖（纤维二糖，龙胆二糖，异麦芽糖，乳糖，麦芽糖，用吡啶溶液中的N-甲基双-（三氟乙酰胺）衍生化了黑糖，槐糖和木糖以及三种三糖（异麦芽三糖，麦芽三糖和木三糖），形成三氟乙酰化衍生物。通过1H-nmr光谱法对它们进行分析，以确定光谱的特征和反应产物的分布。对应于还原残基异头质子的峰位于所有其他场的显着下场，并且当它们与其他基团游离或衍生时，通常来自相同碳水化合物的等价信号的场下限为0.4 ppm或更高。异头质子峰的相对位置和H-1和H-2之间的自旋-自旋偶联程度都不会因衍生化类型而有很大变化。但是，对于某些木糖和三种三糖的β-吡喃糖形式，自旋-自旋偶联降低。在所有实施例中，除了一些其中H-2相对于吡喃糖环赤道取向的实施例之外，通过三氟乙酰化提高或不改变α-吡喃糖的比例。
• Purification and Characterization of a Novel Fungal α-Glucosidase from<i>Mortierella alliacea</i>with High Starch-hydrolytic Activity
  作者：Yoshio TANAKA、Tsunehiro AKI、Yûki HIDAKA、Yûji FURUYA、Seiji KAWAMOTO、Seiko SHIGETA、Kazuhisa ONO、Osamu SUZUKI

  DOI：10.1271/bbb.66.2415

  日期：2002.1

  The fungal strain Mortierella alliacea YN-15 is an arachidonic acid producer that assimilates soluble starch despite having undetectable α-amylase activity. Here, a α-glucosidase responsible for the starch hydrolysis was purified from the culture broth through four-step column chromatography. Maltose and other oligosaccharides were less preferentially hydrolyzed and were used as a glucosyl donor for transglucosylation by the enzyme, demonstrating distinct substrate specificity as a fungal α-glucosidase. The purified enzyme consisted of two heterosubunits of 61 and 31 kDa that were not linked by a covalent bond but stably aggregated to each other even at a high salt concentration (0.5 M), and behaved like a single 92-kDa component in gel-filtration chromatography. The hydrolytic activity on maltose reached a maximum at 55°C and in a pH range of 5.0-6.0, and in the presence of ethanol, the transglucosylation reaction to form ethyl-α-D-glucoside was optimal at pH 5.0 and a temperature range of 45-50°C.

  真菌菌株Mortierella alliacea YN-15是一种能利用可溶性淀粉生产花生四烯酸的菌株，尽管其α-淀粉酶活性无法检测到。在此，通过四步柱层析从培养液中纯化出一种负责淀粉水解的α-葡萄糖苷酶。该酶对麦芽糖和其他低聚糖的水解优先性较低，但能将其作为葡萄糖供体进行转葡萄糖基作用，显示出作为真菌α-葡萄糖苷酶的独特底物特异性。纯化的酶由两个分别为61和31 kDa的异亚基组成，它们之间没有通过共价键连接，但在高盐浓度（0.5 M）下稳定地聚集在一起，在凝胶过滤层析中表现出如同一个92 kDa组分的特性。该酶对麦芽糖的水解活性在55°C和pH 5.0-6.0范围内达到最大，并且在存在乙醇的情况下，形成乙基-α-D-葡萄糖苷的转葡萄糖基反应在pH 5.0和温度范围45-50°C时最优。
• Stereoselective α-Glucosylation with Tetra-<i>O</i>-benzyl-α-D-glucose and a Mixture of Trimethylsilyl Bromide, Cobalt(II) Bromide, Tetrabutylammonium Bromide, and a Molecular Sieve. A Synthesis of 3,6-Di-<i>O</i>-(α-D-glucopyranosyl)-D-glucose
  作者：Shinkiti Koto、Naohiko Morishima、Chiharu Kusuhara、Shigeko Sekido、Toyosaku Yoshida、Shonosuke Zen

  DOI：10.1246/bcsj.55.2995

  日期：1982.9

  A mixture of trimethylsilyl bromide, cobalt(II) bromide, tetrabutylammonium bromide, and a molecular sieve (4A) is effective for the stereoselective, one-stage α-glucosylation of alcohol with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in dichloromethane. Using this procedure, several disaccharide derivatives as well as O-α-D-glucopyranosyl-(1→3)]-O-[α-D-glucopyranosyl-(1→6)]-D-glucopyranose are synthesized

  三甲基溴化甲硅烷、溴化钴 (II)、溴化四丁基铵和分子筛 (4A) 的混合物可有效用于醇与 2,3,4,6-四-O-苄基的立体选择性、一步 α-葡萄糖基化-α-D-吡喃葡萄糖在二氯甲烷中。使用此程序，合成了几种二糖衍生物以及 O-α-D-吡喃葡萄糖基-(1→3)]-O-[α-D-吡喃葡萄糖基-(1→6)]-D-吡喃葡萄糖。
• Glucoamylase Originating from<i>Schwanniomyces occidentalis</i>Is a Typical α-Glucosidase
  作者：Fumiaki SATO、Masayuki OKUYAMA、Hiroyuki NAKAI、Haruhide MORI、Atsuo KIMURA、Seiya CHIBA

  DOI：10.1271/bbb.69.1905

  日期：2005.1

  A starch-hydrolyzing enzyme from Schwanniomyces occidentalis has been reported to be a novel glucoamylase, but there is no conclusive proof that it is glucoamylase. An enzyme having the hydrolytic activity toward soluble starch was purified from a strain of S. occidentalis. The enzyme showed high catalytic efficiency (kcat⁄Km) for maltooligosaccharides, compared with that for soluble starch. The product anomer was α-glucose, differing from glucoamylase as a β-glucose producing enzyme. These findings are striking characteristics of α-glucosidase. The DNA encoding the enzyme was cloned and sequenced. The primary structure deduced from the nucleotide sequence was highly similar to mold, plant, and mammalian α-glucosidases of α-glucosidase family II and other glucoside hydrolase family 31 enzymes, and the two regions involved in the catalytic reaction of α-glucosidases were conserved. These were no similarities to the so-called glucoamylases. It was concluded that the enzyme and also S. occidentalis glucoamylase, had been already reported, were typical α-glucosidases, and not glucoamylase.

  来自西方施瓦尼霉的淀粉水解酶被报道为一种新型的葡萄糖淀粉酶，但尚无确凿证据表明其为葡萄糖淀粉酶。从一种西方施瓦尼霉株中分离出一种对可溶性淀粉具有水解活性的酶。与对可溶性淀粉的活性相比，该酶对麦芽低聚糖表现出高催化效率（kcat⁄Km）。产物的异形体为α-葡萄糖，与能产生β-葡萄糖的葡萄糖淀粉酶不同。这些发现是α-葡萄糖苷酶的显著特征。编码该酶的DNA被克隆并测序。从核苷酸序列推导出的一级结构与真菌、植物和哺乳动物的α-葡萄糖苷酶II族及其他糖苷水解酶家族31的α-葡萄糖苷酶高度相似，并且与α-葡萄糖苷酶催化反应相关的两个区域是保守的。与所谓的葡萄糖淀粉酶并无相似之处。最终得出的结论是，该酶以及已经报道的西方施瓦尼霉的葡萄糖淀粉酶都是典型的α-葡萄糖苷酶，而不是葡萄糖淀粉酶。
• Purification and Characterization of a New Type of α-Glucosidase from<i>Paecilomyces lilacinus</i>That Has Transglucosylation Activity to Produce α-1,3- and α-1,2-Linked…
  作者：Isao KOBAYASHI、Masahiro TOKUDA、Hiroyuki HASHIMOTO、Takashi KONDA、Hirofumi NAKANO、Sumio KITAHATA

  DOI：10.1271/bbb.67.29

  日期：2003.1

  A fungus producing an α-glucosidase that synthesizes α-1,3- and α-1,2-linked glucooligosaccharides by transglucosylation was isolated and identified as Paecilomyces lilacinus. The cell-bound enzyme responsible for the synthesis was extracted by suspension of mycelia with 0.1 M phosphate buffer (pH 8.0), and the extract was purified. The molecular weight and the isoelectric point were estimated to be 54,000 and 9.1, respectively. The enzyme was most active at pH 5.0 and 65°C. The enzyme hydrolyzed maltose, nigerose, and kojibiose. The enzyme also hydrolyzed soluble starch and amylose with the rate toward maltose. p-Nitrophenyl α-glucoside and isomaltose were not good substrates. The enzyme had high transglucosylation activity to synthesize oligosaccharides containing α-1,3- and α-1,2-linkages. At an early stage of the reaction, considerable maltotriose, 4-O-α-nigerosyl-D-glucose, and 4-O-α-kojibiosyl-D-glucose were synthesized. Afterwards, nigerose and kojibiose were accumulated gradually with glucose as an acceptor.

  一种产生α-葡萄糖苷酶的真菌被分离并鉴定为紫色土胞霉（Paecilomyces lilacinus）。负责合成的细胞结合酶通过将菌丝体悬浮于0.1 M磷酸盐缓冲液（pH 8.0）中提取，并对提取物进行了纯化。估计其分子量和等电点分别为54,000和9.1。该酶在pH 5.0和65°C下最为活跃。该酶水解麦芽糖、黑麦芽糖和异麦芽糖。该酶还以与麦芽糖相同的速率水解可溶性淀粉和直链淀粉。对对硝基苯基α-葡萄糖苷和异麦芽糖的底物活性较低。该酶具有较高的转葡萄糖基化活性，可以合成含有α-1,3-和α-1,2-连接的寡糖。在反应早期，合成了相当数量的麦芽三糖、4-O-α-黑麦芽糖基-D-葡萄糖和4-O-α-异麦芽糖基-D-葡萄糖。随后，黑麦芽糖和异麦芽糖以葡萄糖作为受体逐渐积累。