beta-D-吡喃葡萄糖基-(1->3)-beta-D-吡喃葡萄糖基-(1->3)-beta-D-吡喃葡萄糖基-(1->3)-D-吡喃葡萄糖

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: beta-D-吡喃葡萄糖基-(1->3)-beta-D-吡喃葡萄糖基-(1->3)-beta-D-吡喃葡萄糖基-(1->3)-D-吡喃葡萄糖
• 中文别名: 昆布四糖
• 英文名称: laminaritetraose
• 英文别名: cellotetraose；Glcβ1-3Glcβ1-3Glcβ1-3Glc；Laminaritetraose；(3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol
• 化学式: C₂₄H₄₂O₂₁
• 分子量: 666.585
• InChiKey: OLBQXBHLZOAVSV-UKPDYPBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.4
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  348
• 氢给体数：
  14
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  beta-D-吡喃葡萄糖基-(1->3)-beta-D-吡喃葡萄糖基-(1->3)-beta-D-吡喃葡萄糖基-(1->3)-D-吡喃葡萄糖 在 MATRLMMLLGMIALCMSGVAGQYNYDEVLEKSILFYEAERSGDLPANNRIPYRGDSALGDQGNQGQDLTGGWYDAGDHVKFGFPMAFATTTLAWGILEFRDGYEAAGQYNLALDSIRWTLNYFLKAHVSDNEFYGQVGDANTDHAYWGRPEDMTMERPAWSISPSAPGSDLAAETAAALAAGYLVFRDSDAAFANNLLAHSRTLYDFALNRGIYSQSISNAAGFYASSAYEDELAWGAAWLYRATEEQEYLDRAYEFGTTTNTAWAYDWNEKIVGYQLLLTTSAGQTDFLPRVENFLRNWFPGGSVQYTPLGLAWLAQWGPNRYAANAAFIALVSAKYNILASESEQFARSQIHYMLGDAGRSYVVGFGNNPPQQPHHRSSSCPDQPAECDWDEFNQPGPNYQILYGALVGGPDQNDQFEDLRSDYIRNEVANDYNAGFQGAVAALRAIQLRDGK 作用下， 以 aq. acetate buffer 为溶剂， 生成 laminaribiose 、 laminaritriose
  参考文献：
  名称：

  Cloning and expression of the cold-adapted endo-1,4-β-glucanase gene from Eisenia fetida

  摘要：

  Biofuel production from plant-derived lignocellulosic material using fungal cellulases is facing cost-effective challenges related to high temperature requirements. The present study identified a cold-adapted cellulase named endo-1,4-beta-glucanase (EF-EG2) from the earthworm Eisenia fetida. The gene was cloned in the cold-shock expression vector (pCold I) and functionally expressed in Escherichia coli ArcticExpress RT (DE3). The gene consists of 1368 bp encoding 456 amino acid residues. The amino acid sequence shares sequence homology with the endo-1,4-beta-glucanases of Eisenia andrei (98%), Pheretima hilgendorfi (79%), Perineresis brevicirris (63%), and Strongylocentrotus nudus (58%), which all belong to glycoside hydrolase family 9. Purified recombinant EF-EG2 hydrolyzed soluble cellulose (carboxymethyl cellulose), but not insoluble (powdered cellulose) or crystalline (Avicel) cellulose substrates. Thin-layer chromatography analysis of the reaction products from 1,4-beta-linked oligosaccharides of various lengths revealed a cleavage mechanism consistent with endoglucanases (not exoglucanases). The enzyme exhibited significant activity at 10 degrees C (38% of the activity at optimal 40 degrees C) and was stable at pH 5.0-9.0, with an optimum pH of 5.5. This new cold-adapted cellulase could potentially improve the cost effectiveness of biofuel production. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carbpol.2013.09.057
• 作为产物：
  描述：

  benzyl β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl-(1->3)-β-D-glucopyranoside 在 palladium diacetate 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 生成 beta-D-吡喃葡萄糖基-(1->3)-beta-D-吡喃葡萄糖基-(1->3)-beta-D-吡喃葡萄糖基-(1->3)-D-吡喃葡萄糖
  参考文献：
  名称：

  US2005/65114

  摘要：

  公开号：

文献信息

• Characterization of Recombinant Yeast Exo-β-1,3-Glucanase (Exg 1p) Expressed in Escherichia coli Cells
  作者：Kanako SUZUKI、Tomio YABE、Yutaka MARUYAMA、Keietsu ABE、Tasuku NAKAJIMA

  DOI：10.1271/bbb.65.1310

  日期：2001.1

  Yeast exo-β-1,3-glucanse gene (EXG1) was expressed in Escherichia coli and the recombinant enzyme (EXg1p) was characterized. The recombinant Exg1p had an apparent molecular mass of 45 kDa by SDS-PAGE and the enzyme has a broad specificity for β-1,3-link-ages as well as β-1,6-linkages, and also for other β-glucosidic linked substrates, such as cellobiose and pNPG. Kinetic analyses indicate that the enzyme prefers small substrates such as laminaribiose, gentiobiose, and pNPG rather than polysaccharide substrates, such as laminaran or pustulan. With a high concentration of laminaribiose, the enzyme catalyzed transglucosidation forming laminarioligosaccharides. The enzyme was strongly inhibited with high concentrations of laminaran.

  酵母 exo-β-1,3-葡聚糖酶基因 (EXG1) 在大肠杆菌中表达，并对重组酶 (EXg1p) 进行了特性分析。重组的 Exg1p 的表观分子量为 45 kDa（通过 SDS-PAGE 测定），该酶对 β-1,3 键和 β-1,6 键具有广泛的特异性，并且对其他 β-葡萄糖苷链接的底物（如纤维二糖和 pNPG）也具有活性。动力学分析表明，该酶更喜欢小底物，如兰梅糖、根茎糖和 pNPG，而不是多糖底物，如兰梅糖或双聚赖氨酸。高浓度的兰梅糖时，该酶催化转葡萄糖作用形成兰梅寡糖。在高浓度的兰梅糖下，该酶受到强烈抑制。
• 1,3-Dideoxynojirimycin-3-yl glycosides of β-(1→3)- and β-(1→6)-linked gluco-oligosaccharides
  作者：Regine Blattner、Richard H. Furneaux、Zbigniew Pakulski

  DOI：10.1016/j.carres.2006.05.004

  日期：2006.9

  glycosyl trichloroacetimidates as glycosylating agents were used to prepare the five 1,3-dideoxynojirimycin-3-yl β-(1→3)-linked oligo-glucosides ( 1 – 5) and also the β-(1→6)-bonded glucobiose (gentiobiose)-based analogue 6 as potential fungicides. In the course of the work, the β-(1→6), β-(1→6)-linked analogue 8 of 6 and 6- O - and 4- O -β-glucopyranosyl-deoxynojirimycins 7 and 9 , respectively, were also

  摘要使用涉及以O-乙酰化的糖基三氯乙酰亚氨酸酯为糖基化剂的标准化学方法，制备了5种与1,3-二脱氧野oji菌素-3-基β-（1→3）连接的低聚葡糖苷（1-5），以及β-（1→6）键合的葡萄糖二糖（龙胆二糖）基类似物6作为潜在的杀菌剂。在工作过程中，分别由β-（1→6），β-（1→6）连接的6和6-O-和4-O-β-吡喃葡萄糖基-脱氧野oji霉素7和9的类似物8，也产生了。
• NOVEL FUCOSYLATED OLIGOSACCHARIDES AND PROCESS FOR THEIR PREPARATION
  申请人：Biotie Therapies Corp.

  公开号：EP1228079B1

  公开（公告）日：2004-08-18
• Synthesis of sulfated oligosaccharide glycosides having high anti-HIV activity and the relationship between activity and chemical structure
  作者：Kaname Katsuraya、Hideki Nakashima、Naoki Yamamoto、Toshiyuki Uryu

  DOI：10.1016/s0008-6215(98)00315-2

  日期：1999.2

  Sulfated laminara-oligosaccharide glycosides having high anti-human immunodeficiency virus (HIV) activities were synthesized from laminara-tetraose, -pentaose and -hexaose. The oligosaccharide glycosides were synthesized by treating peracetylated beta-oligosaccharides with various alcohols and Lewis acid catalysts. The effects of the number of glucose residues and the alkyl chain-length on anti-HIV activity were examined. The anti-HIV activity of sulfated dodecyl laminara-pentaosides and -hexaosides increased with increasing degree of sulfation (DS) and the pentaoside having an almost fully-sulfated saccharide portion had the highest activity, whereas for the hexaoside a somewhat lower DS manifested the highest activity. Sulfated laminara-oligosaccharide glycosides having fluoroalkyl-containing aglycons of high hydrophobicity showed potent inhibitory effects against HIV infection, in contrast, hydrophilic substituents containing oligo(ethyleneoxy) groups as aglycons in the sulfated oligosaccharides did not show high anti-HIV activity. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of Epoxyalkyl (1→3)‐β‐<scp>D</scp>‐Oligoglucosides
  作者：Gang‐Liang Huang、Man‐Xi Liu、Xin‐Ya Mei

  DOI：10.1081/scc-200032424

  日期：2004.1.1

  We describe an approach for the synthesis of (1 --> 3)-beta-D-oligosaccharide derivatives 10-18. 1-9 were synthesized by treating peracetylated (1 --> 3)-beta-D-oligosaccharides with the corresponding alkenyl alcohols and Lewis acid (SnCl4) catalyst. Epoxidation of the corresponding alkenyl oligoglucosides took place by m-CPBA. NaOMe in dry methanol was used for the deacetylation of the blocked derivatives, to give 10-18 in overall yields of 25-32%.