swietenose | 902-54-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: swietenose
• 英文别名: α-D-Galp(1->6)-D-Galp；α-(1->6)-Galactobiose；6-O-alpha-D-galactopyranosyl-D-galactopyranose；(3R,4S,5R,6R)-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
• CAS: 902-54-5
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: DLRVVLDZNNYCBX-BQYJSGCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 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：

  swietenose 、 乙酸酐 在 吡啶 作用下， 反应 5.0h， 生成 Acetic acid (3R,4S,5S,6R)-2,3,5-triacetoxy-6-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of digalactosyl diacylglycerols and their structure–inhibitory activity on human lanosterol synthase

  摘要：

  Digalactosyl and monogalactocyl diacylglycerols (DGDG and MGDG), which were identified as anti-hyperlipemia active components in Colocasia esculenta (Taro), were synthesized. The inhibitory activity of DGDG, MGDG and related compounds on human lanosterol synthase was evaluated as anti-hyperlipemic activity. DGDG with two myristoyl groups at both sn-1 and sn-2 positions and with an oleoyl group at the sn-1 position showed the most potent activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.013
• 作为产物：
  描述：

  4-硝基苯基-α-D-吡喃半乳糖苷 在 recombinant Aspergillus nidulans FGSC GH36 α-galactosidase 作用下， 反应 7.0h， 生成 swietenose
  参考文献：
  名称：

  糖苷水解酶家族36的构巢曲霉α-半乳糖苷酶通过转糖基化催化α-半乳糖低聚糖的形成

  摘要：

  来自构巢曲霉（AglC）的α-半乳糖苷酶属于系统发育簇，包含糖苷水解酶家族36（GH36）的真核α-半乳糖苷酶和α-半乳糖寡糖合酶。重组AglC在大肠杆菌中以His-tag融合形式高产量（0.65 g·L -1培养）产生，催化40 m m 4-硝基苯酚α- d-吡喃半乳糖苷具有α-（1→6）区域选择性的高效转糖基化作用，蜜二糖棉子糖或，产生4-硝基苯酚α-收率的37-74％d -Gal p - （1→6） - d -Gal p，α- d -Gal p - （1→6）-α- d-Gal p - （1→6） - d -Glc p和α- d -Gal p - （1→6）-α- d -Gal p - （1→6） - d -Glc p - （α1→β2 ）-d- Fru f（水苏糖）。此外，在10个候选单糖受体（400 m m）和供体4-硝基苯酚α- d-吡喃半乳糖苷（40 m m）中，还获得了由半

  DOI：

  10.1111/j.1742-4658.2010.07763.x

文献信息

• Reverse Reaction of<i>Aspergillus niger</i>APC-9319 α-Galactosidase in a Supersaturated Substrate Solution: Production of α-Linked Galactooligosaccharide (α-GOS)
  作者：Akiko YAMASHITA、Hiroyuki HASHIMOTO、Koki FUJITA、Masamichi OKADA、Shigeharu MORI、Sumio KITAHATA

  DOI：10.1271/bbb.69.1381

  日期：2005.1

  The α-galactosidase that effectively catalyzes a reverse reaction of galactose, Aspergillus niger APC-9319 α-galactosidase, was screened from industrial enzyme preparations for food processing containing α-galactosidase activity. Reverse reaction of A. niger APC-9319 α-galactosidase was performed using a supersaturated solution (90% galactose [w/v]). A. niger APC-9319 α-galactosidase was not inhibited even in high substrate concentration, and effectively catalyzed the reverse reaction. The yield of the reaction product, α-linked galactooligosaccharide (α-GOS), increased greatly as the initial concentration of galactose increased to 90% (w/v), and was more than 50%. Furthermore, the half life of enzyme activity was about three times as long as that using 60% galactose (w/v). α-GOS (1.4 g) was prepared from galactose (3.0 g) by reverse reaction of A. niger APC-9319 α-galactosidase. The α-GOS contained 58% α-galactobiose (α-Gal2), 28% α-galactotriose, and 14% oligosaccharides larger than α-galactotriose. The main component of positional isomers in α-Gal2 was α-1,6Gal2.

  从含有α-半乳糖苷酶活性的食品加工工业酶制剂中筛选出能有效催化半乳糖逆反应的Aspergillus niger APC-9319 α-半乳糖苷酶。使用过饱和溶液（90%半乳糖[w/v]）进行A. niger APC-9319 α-半乳糖苷酶的逆反应。即使在高的底物浓度下，A. niger APC-9319 α-半乳糖苷酶也没有被抑制，并且能有效催化逆反应。反应产物α-半乳糖寡糖（α-GOS）的产率随着半乳糖初始浓度的增加而大幅增加，达到90%（w/v）时超过50%。此外，酶活性的半衰期约为使用60%半乳糖（w/v）时的三倍。通过A. niger APC-9319 α-半乳糖苷酶的逆反应，从3.0 g半乳糖制备了1.4 g的α-GOS。α-GOS含有58%的α-半乳二糖（α-Gal2），28%的α-半乳三糖，以及14%的大于α-半乳三糖的寡糖。α-Gal2中的主要位置异构体是α-1,6Gal2。
• A non-ionic seed-gum from cassia corymbosa
  作者：Kailash Tewari、Neeta Khare、Vandana Singh、Purna C. Gupta

  DOI：10.1016/0008-6215(84)85011-9

  日期：1984.12

  Abstract A polysaccharide has been extracted from Cassia corymbosa seeds with cold, acidulated water, and purified to give a water-soluble product containing d -galactose and d -mannose in 4:7 molar ratio. Acid-catalyzed fragmentation, periodate oxidation, methylation, and enzymic hydrolysis showed that the seed gum has a branched structure consisting of a linear chain of β- d -(1→4)-linked mannopyranosyl

  摘要用冷酸水从决明子种子中提取多糖，纯化后制成摩尔比为4：7的d-半乳糖和d-甘露糖的水溶性产物。酸催化的裂解，高碘酸盐氧化，甲基化和酶水解表明，种子胶具有由β-d-（1→4）连接的甘露吡喃糖基单元的线性链组成的支链结构，其中一些在O-处被取代。 6由两个α-d-（1→6）吡喃半乳糖苷单元相互糖苷键连接。半乳甘露聚糖的甲基化分析提供了2,3,4-三-和2,3,4,6-四-O-甲基半乳糖，以及2,3-二-和2,3,6-三-O-甲基甘露糖，以2：2：2：5的摩尔比。甲基化和高碘酸氧化研究均显示约36.4％的端基。这些结果的意义，
• Improving Properties of a Novel β-Galactosidase from Lactobacillus plantarum by Covalent Immobilization
  作者：Rocio Benavente、Benevides Pessela、Jose Curiel、Blanca de las Rivas、Rosario Muñoz、Jose Guisán、Jose Mancheño、Alejandra Cardelle-Cobas、Ana Ruiz-Matute、Nieves Corzo

  DOI：10.3390/molecules20057874

  日期：——

  A novel β-galactosidase from Lactobacillus plantarum (LPG) was over-expressed in E. coli and purified via a single chromatographic step by using lowly activated IMAC (immobilized metal for affinity chromatography) supports. The pure enzyme exhibited a high hydrolytic activity of 491 IU/mL towards o-nitrophenyl β-d-galactopyranoside. This value was conserved in the presence of different divalent cations and was quite resistant to the inhibition effects of different carbohydrates. The pure multimeric enzyme was stabilized by multipoint and multisubunit covalent attachment on glyoxyl-agarose. The glyoxyl-LPG immobilized preparation was over 20-fold more stable than the soluble enzyme or the one-point CNBr-LPG immobilized preparation at 50 °C. This β-galactosidase was successfully used in the hydrolysis of lactose and lactulose and formation of different oligosaccharides was detected. High production of galacto-oligosaccharides (35%) and oligosaccharides derived from lactulose (30%) was found and, for the first time, a new oligosaccharide derived from lactulose, tentatively identified as 3'-galactosyl lactulose, has been described.

  来自植物乳杆菌 (LPG) 的新型 β-半乳糖苷酶在大肠杆菌中过表达，并使用低活化 IMAC（用于亲和层析的固定金属）支持物通过单一层析步骤进行纯化。纯酶对邻硝基苯基 β-d-吡喃半乳糖苷表现出 491 IU/mL 的高水解活性。该值在不同二价阳离子存在下是保守的，并且对不同碳水化合物的抑制作用具有相当的抵抗力。通过乙醛酰琼脂糖上的多点和多亚基共价连接来稳定纯多聚体酶。在 50 °C 下，乙醛酰-LPG 固定化制剂比可溶性酶或单点 CNBr-LPG 固定化制剂稳定 20 倍以上。该β-半乳糖苷酶成功用于乳糖和乳果糖的水解，并检测到不同寡糖的形成。低聚半乳糖 (35%) 和乳果糖衍生低聚糖 (30%) 的高产量被发现，并且首次描述了一种新的乳果糖衍生低聚糖，暂时鉴定为 3'-半乳糖基乳果糖。
• Characterization of Properties and Transglycosylation Abilities of Recombinant α-Galactosidase from Cold-Adapted Marine Bacterium Pseudoalteromonas KMM 701 and Its C494N and D451A Mutants
  作者：Irina Bakunina、Lubov Slepchenko、Stanislav Anastyuk、Vladimir Isakov、Galina Likhatskaya、Natalya Kim、Liudmila Tekutyeva、Oksana Son、Larissa Balabanova

  DOI：10.3390/md16100349

  日期：——

  (α-PsGal) from the cold-adapted marine bacterium Pseudoalteromonas sp. KMM 701, and its mutants D451A and C494N, were studied in terms of their structural, physicochemical, and catalytic properties. Homology models of the three-dimensional α-PsGal structure, its active center, and complexes with D-galactose were constructed for identification of functionally important amino acid residues in the active site

  一种新的野生型重组冷活性α-d-半乳糖苷酶（α-PsGal），来自适应寒冷的海洋细菌Pseudoalteromonas sp。研究了KMM 701及其突变体D451A和C494N的结构，物理化学和催化特性。建立了三维α-PsGal结构，其活性中心以及与D-半乳糖的复合物的同源性模型，以利用酶的α-半乳糖苷酶的晶体结构鉴定酶活性位点中功能上重要的氨基酸残基。嗜酸乳杆菌为模板。野生α-PsGal和突变体C494N的圆二色性光谱大致相同。C494N突变降低了保留酶与标准对硝基苯基-α-吡喃半乳糖苷（pNP-α-Gal）亲和力的效率。薄层色谱法，使用基质辅助激光解吸/电离质谱法和核磁共振波谱法鉴定反应混合物中的糖基转移产物。α-PsGal具有狭窄的受体特异性。果糖，木糖，岩藻糖和葡萄糖在转糖基化反应中作为受体没有活性。α-PsGal由蜜三糖以及-α（1→6）-和-α（1→3）连接的对硝基苯基-合成
• Preparation of α-galactooligoglycosides by cell walls from Cryptococcus laurentii using a novel α-galactosyl donor
  作者：Vladimír Mastihuba、Mária Mastihubová、Miroslav Belák、Jana Dudíková、Elena Karnišová Potocká、Ladislav Petruš

  DOI：10.1016/j.tetasy.2017.07.007

  日期：2017.8

  The cell walls of an acapsular strain of the yeast Cryptococcus laurentii catalyze the regioselective formation of alpha-galactooligosaccharides through self-condensation of 4-nitrophenyl alpha-D-galactopyranoside and of a novel activated ot-galactosyl donor 2,2,2-trifluoroethyl of-o-galactopyranoside. The latter substance can be easily prepared by several methods and is highly soluble in water and therefore can be used in higher initial concentrations suppressing secondary product hydrolysis. The preparative reaction catalyzed by cell walls provided 17.4% and 2% of corresponding 2,2,2-trifluoroethyl galactobioside and galactotrioside, respectively, while the reaction with 4-nitrophenyl alpha-D-galactopyranoside provided the corresponding 4-nitrophenyl galactobioside and galactotrioside in 6.6 and 2.5% yields, respectively. The reactions proceeded with strict alpha-(1 -> 6)-regioselectivity. (C) 2017 Elsevier Ltd. All rights reserved.