panose | 490-40-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: panose
• 英文别名: α-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1->4)-D-glucopyranose；α-isomaltosyl-(1->4)-D-glucose；α-isomaltosyl-(1->4)-glucose；α-D-Glcp-(1->6)-α-D-Glcp-(1->4)-D-Glcp；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)tetrahydropyran-3-yl]oxy-tetrahydropyran-2-yl]methoxy]tetrahydropyran-3,4,5-triol；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol
• CAS: 490-40-4；3005-45-6；3425-21-6；7244-19-1；34218-17-2；117466-16-7
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: OWEGMIWEEQEYGQ-UCFFOQEWSA-N

物化性质

• 熔点：
  213 °C
• 沸点：
  860.9±65.0 °C(Predicted)
• 密度：
  1.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  269
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  panose 在 Geobacillus stearothermophilus α-glucosidase 作用下， 反应 18.0h， 生成 葡萄糖
  参考文献：
  名称：

  Bioengineering of Leuconostoc mesenteroides Glucansucrases That Gives Selected Bond Formation for Glucan Synthesis and/or Acceptor-Product Synthesis

  摘要：

  The variations in glucosidic linkage specificity observed in products of different glucansucrases appear to be based on relatively small differences in amino acid sequences in their sugar-binding acceptor subsites. Various amino acid mutations near active sites of DSRBCB4 dextransucrase from Leuconostoc mesenteroides B-1299CB4 were constructed. A triple amino acid mutation (S642N/E643N/V644S) immediately next to the catalytic D641 (putative transition state stabilizing residue) converted DSRBCB4 enzyme from the synthesis of mainly alpha-(1 -> 6) dextran to the synthesis of alpha-(1 -> 6) glucan containing branches of alpha-(1 -> 3) and alpha-(1 -> 4) glucosidic linkages. The subsequent introduction of mutation V532P/V535I, located next to the catalytic D530 (nucleophile), resulted in the synthesis of an alpha-glucan containing increased branched alpha-(1 -> 4) glucosidic linkages (approximately 11%). The results indicate that mutagenesis can guide glucansucrase toward the synthesis of various oligosaccharides or novel polysaccharides with completely altered linkages without compromising high transglycosylation activity and efficiency.

  DOI：

  10.1021/jf104629g
• 作为产物：
  描述：

  麦芽糖 在 3-(N-morpholino)propanesulfonic acid buffer 、 disproportionating enzyme from Bacillus sp. NRRL B-21195 作用下， 反应 160.0h， 生成 panose
  参考文献：
  名称：

  A synergistic reaction mechanism of a cycloalternan-forming enzyme and a d-glucosyltransferase for the production of cycloalternan in Bacillus sp. NRRL B-21195

  摘要：

  Cycloalternan-forming enzyme (CAFE) was first described as the enzyme that produced cycloalternan from alternan. In this study, we found that a partially purified preparation of CAFE containing two proteins catalyzed the synthesis of cycloalternan from maltooligosaccharides, whereas the purified CAFE alone was unable to do so. In addition to the 117 kDa CAFE itself, the mixture also contained a 140 kDa protein. The latter was found to be a disproportionating enzyme (DE) that catalyzes transfer of a D-glucopyranosyl residue from the non-reducing end of one maltooligosaccharide to the non-reducing end of another, forming an isomaltosyl residue at the non-reducing end. CAFE then transfers the isomaltosyl residue to the non-reducing end of another isomaltosyl maltooligosaccharide, to form an alpha-isomaltosyl-(1-->3)-alpha-isomaltosyl-(1-->4)-maltooligosaccharide, and subsequently catalyzes a cyclization to produce cycloalternan. Thus, DE and CAFE act synergistically to produce cycloalternan directly from maltodextrin or starch. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00375-6

文献信息

• Dehydrative Glycosylation Using Heptabenzyl Derivatives of Glucobioses and Lactose
  作者：Shinkiti Koto、Naohiko Morishima、Sonoko Shichi、Hisamitsu Haigoh、Motoko Hirooka、Mitsuko Okamoto、Takashi Higuchi、Koichi Shimizu、Yosuke Hashimoto、Terumi Irisawa、Hidehiro Kawasaki、Yasushi Takahashi、Masayo Yamazaki、Yoko Mori、Keiko Kudo、Takako Ikegaki、Sonoe Suzuki、Shonosuke Zen

  DOI：10.1246/bcsj.65.3257

  日期：1992.12

  reducing tribenzylglucose moiety of the nonreducing tetrabenzylglucosyl residue and on the class of the OH group to be glycosylated. The use of a quaternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine made all but the β(1→2)-linked biosyl donor undergo α-condensation. Several new linear trisaccharides were obtained via debenzylation

  D-吡喃葡萄糖的 2-、3-、4-和 6-OH 基团与葡萄糖二糖的七-O-苄基衍生物的脱水糖基化（OD-吡喃葡萄糖基-（1→n）-D-吡喃葡萄糖；n = 2， 3、4 或 6) 和乳糖，在对硝基苯磺酰氯、三氟甲磺酸银和三乙胺的三元混合物在二氯甲烷中的存在下表明反应的选择性取决于异头构型和与还原三苄基葡萄糖的连接位置非还原性四苄基葡萄糖残基的部分和要糖基化的 OH 基团的类别。使用对硝基苯磺酰氯、三氟甲磺酸银、N,N-二甲基乙酰胺和三乙胺的四元混合物使除 β(1→2)-连接的生物基供体以外的所有物质都发生 α-缩合。
• The Stereoselective Dehydrative α-Glucosylation Using 6-<i>O</i>-Acetyl- and 6-<i>O</i>-<i>p</i>-Nitrobenzoyl-2,3,4-tri-<i>O</i>-benzyl-D-glucopyranoses
  作者：Shinkiti Koto、Naohiko Morishima、Yasuhiro Kihara、Hideko Suzuki、Shigeharu Kosugi、Shonosuke Zen

  DOI：10.1246/bcsj.56.188

  日期：1983.1

  The stereoselective synthesis of α-linked glucobiose derivatives using 6-O-acetyl- or 6-O-p-nitrobenzoyl-2,3,4-tri-O-benzyl-D-glucopyranose and a ternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluorometh-anesulfonate, and triethylamine in dichloromethane is described.

  使用 6-O-乙酰基-或 6-Op-硝基苯甲酰基-2,3,4-三-O-苄基-D-吡喃葡萄糖和对硝基苯磺酰氯、三氟甲基银的三元混合物立体选择性合成α-连接的葡萄糖二糖衍生物描述了-烷磺酸盐和三乙胺的二氯甲烷溶液。
• Branched cyclic tetrasaccharide, process for producing the same, and use
  申请人：——

  公开号：US20040236097A1

  公开（公告）日：2004-11-25

  The object of the present invention is to provide a novel glycosyl derivative of cyclotetrasaccharide represented by cyclo{→6)-&agr;-D-glucopyranosyl-(1→3)-&agr;-D-glucopyranosyl-(1→6)-&agr;-D-glucopyranosyl-(1→3)-&agr;-D-glucopyranosyl-(1→}, and it is solved by providing a branched cyclotetrasaccharide, wherein one or more hydrogen atoms in the hydroxyl groups of cyclotetrasaccharide are replaced with an optionally substituted glycosyl group, with the proviso that, when only one hydrogen atom in the C-6 hydroxyl group among the above hydrogen atoms is substituted with an optionally-substituted glycosyl group, the substituted glycosyl group is one selected from those excluding D-glucosyl group.

  本发明的目的是提供一种新型的环四糖衍生物，其表示为环{→6)-α-D-葡萄糖吡喃糖苷-(1→3)-α-D-葡萄糖吡喃糖苷-(1→6)-α-D-葡萄糖吡喃糖苷-(1→3)-α-D-葡萄糖吡喃糖苷-(1→}。通过提供一种分支的环四糖，解决了这个问题，其中环四糖的羟基中的一个或多个氢原子被可选的取代糖基所取代，条件是，当上述氢原子中的C-6羟基中只有一个氢原子被可选取代的糖基所取代时，所取代的糖基是从排除D-葡萄糖基的那些中选择的一个。
• Acceptor reactions of alternansucrase from Leuconostoc mesenteroides NRRL B-1355
  作者：Gregory L. Côté、John F. Fobyt

  DOI：10.1016/0008-6215(82)85013-1

  日期：1982.12

  Extracellular glucansucrases from various bacterial sources, including Leuconostoc mesenteroides, have been shown to catalyze the transfer of glucosyl groups from sucrose to low-molecular-weight acceptor sugars, forming a series of oligosaccharides. An extracellular glucansucrase recently isolated from Leuconostoc mesenteroides NRRL B-1355 synthesizes a polysaccharide consisting of alternating α-(1→6)-

  来自各种细菌来源的细胞外葡聚糖蔗糖，包括肠间叶亮葡菌，已显示出可将葡萄糖基团从蔗糖转移至低分子量受体糖，从而形成一系列寡糖。最近从肠膜肠球菌NRNR B-1355中分离出的一种细胞外葡糖苷酶合成了由交替的α-（1→6）-和α-（1→3）连接的d-葡萄糖残基组成的多糖。我们已经发现，在许多低分子量受体糖存在下，这种酶制剂能够形成α-（1→6）-和α-（1→3）-连接的受体产物。d-葡萄糖仅产生异麦芽糖，没有形成黑糖。相似地，甲基α-d-葡萄糖苷，甲基β-d-葡萄糖苷，麦芽糖和黑糖生成了甲基α-异麦芽糖苷，甲基β-异麦芽糖苷，panose和62-O-α-d-葡萄糖基黑麦芽糖，分别。然而，异麦芽糖同时给出了异麦芽三糖和32-O-α-d-葡萄糖基异麦芽糖。这些初始的受体产物也可以充当受体，并且较高dp产物的结构表明，只有当非还原性葡萄糖受体基团通过α-连接时，才形成（1→3）-α-d-糖苷键。 （
• Structural analysis of chromophore-labeled disaccharides and oligosaccharides by electrospray ionization mass spectrometry and high-performance liquid chromatography/electrospray ionization mass spectrometry
  作者：D. T. Li、G. R. Her

  DOI：10.1002/(sici)1096-9888(199807)33:7<644::aid-jms667>3.0.co;2-f

  日期：1998.7

  Disaccharides and linear oligosaccharides were labeled with p-aminobenzoic ethyl ester (ABEE) chromophore and analyzed by negative ion electrospray ionization mass spectrometry (ESIMS). The formation of glycosylamines rather than reductive amination in the labeling reaction produced many characteristic fragment ions under in source collision-induced dissociation (CID). These ions provided unambiguous

  用对氨基苯甲酸乙酯（ABEE）发色团标记二糖和线性低聚糖，并通过负离子电喷雾电离质谱（ESIMS）进行分析。在源碰撞诱导解离（CID）下，标记反应中糖胺的形成而不是还原胺化产生了许多特征性碎片离子。这些离子提供了糖苷键位置的明确分配。该方法扩展到几种线性寡糖的键合和键合序列的分析。此外，ABEE标记的1-3-，1-4和1-6连接的葡萄糖二糖的异头构型可以根据特征离子的相对丰度进行区分。