1,3-β-D-laminaripentaose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-β-D-laminaripentaose
• 英文别名: laminarapentaose；laminaripentaose；cellopentaose；Laminaripentaose；(3R,4S,5R,6R)-4-[(2S,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-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol
• 化学式: C₃₀H₅₂O₂₆
• 分子量: 828.727
• InChiKey: UUQINGLDFWYORW-IMLBFRLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9
• 重原子数：
  56
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  427
• 氢给体数：
  17
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  1,3-β-D-laminaripentaose 在 MATRLMMLLGMIALCMSGVAGQYNYDEVLEKSILFYEAERSGDLPANNRIPYRGDSALGDQGNQGQDLTGGWYDAGDHVKFGFPMAFATTTLAWGILEFRDGYEAAGQYNLALDSIRWTLNYFLKAHVSDNEFYGQVGDANTDHAYWGRPEDMTMERPAWSISPSAPGSDLAAETAAALAAGYLVFRDSDAAFANNLLAHSRTLYDFALNRGIYSQSISNAAGFYASSAYEDELAWGAAWLYRATEEQEYLDRAYEFGTTTNTAWAYDWNEKIVGYQLLLTTSAGQTDFLPRVENFLRNWFPGGSVQYTPLGLAWLAQWGPNRYAANAAFIALVSAKYNILASESEQFARSQIHYMLGDAGRSYVVGFGNNPPQQPHHRSSSCPDQPAECDWDEFNQPGPNYQILYGALVGGPDQNDQFEDLRSDYIRNEVANDYNAGFQGAVAALRAIQLRDGK 作用下， 以 aq. acetate buffer 为溶剂， 生成 laminaribiose
  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：

  β-D-glucopyranosyl-(1->3)-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 2.5h， 生成 1,3-β-D-laminaripentaose
  参考文献：
  名称：

  US2005/65114

  摘要：

  公开号：

文献信息

• Synthesis of sulfated alkyl malto- and laminara-oligosaccharides with potent inhibitory effects on AIDS virus infection
  作者：Kaname Katsuraya、Naoya Ikushima、Nahoko Takahashi、Tadao Shoji、Hideki Nakashima、Naoki Yamamoto、Takashi Yoshida、Toshiyuki Uryu

  DOI：10.1016/0008-6215(94)80021-9

  日期：1994.7

  A series of sulfated alkyl oligosaccharides, including a sulfate dodecyl laminarapentaoside and a sulfated octadecyl maltohexaoside with potent anti-human immunodeficiency virus (HIV) activity, has been synthesized. An alkyl oligosaccharide in which a long alkyl group is bonded to the reducing end of the oligosaccharide was first synthesized in high yield. Peracetylated oligosaccharides reacted with

  合成了一系列硫酸化的烷基寡糖，包括具有有效抗人免疫缺陷病毒（HIV）活性的硫酸化十二烷基十二烷基戊糖苷和硫酸化十八烷基麦芽六糖苷。首先以高收率合成了其中长烷基键合至寡糖的还原端的烷基寡糖。过乙酰化的低聚糖与路易斯酸作为催化剂的脂肪族醇（如1-癸基醇和1-十二烷基醇）反应。如在α和β过乙酰化的糖苷的糖基化中一样，β异头异构体仅反应，在高温下用乙酸钠-乙酸酐进行乙酰化以使β异头异构体的比例最大化。
• 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。
• Use of modified oligo-β-(1,3)-glucans for treating diseases of the immune system, oligo-β-(1,3)-glucan-(1,3)-mannose, oligo-β-(1,3)-glucan-(1,3)-mannitol and derivatives thereof, methods for preparing them and medicaments containing them
  申请人：Yvin Jean-Claude

  公开号：US08367641B2

  公开（公告）日：2013-02-05

  The present invention relates to the use of at least one compound of formula (I) or (II), in which R1 is H and n is an integer from 2 to 10, for the preparation of a medicament for treating diseases chosen from the group comprising tumour, cancer, viral disease, bacterial disease, fungal disease, disease of the immune system, auto-immune disease or disease linked to a deficiency in immunostimulation, in human beings and warm-blooded animals. The invention also relates to new products having a mannose or mannitol termination as well as a method for preparing them.

  本发明涉及使用式(I)或(II)中至少一种化合物，其中R1为H，n为2至10的整数，用于制备用于治疗人类和温血动物中所选疾病的药物，所述疾病包括肿瘤、癌症、病毒性疾病、细菌性疾病、真菌性疾病、免疫系统疾病、自身免疫疾病或与免疫刺激缺乏有关的疾病。该发明还涉及具有甘露糖或甘露醇末端的新产品以及其制备方法。
• New 4-deoxy-(1→3)-β-d-glucan-based oligosaccharides and their immunostimulating potential
  作者：Vaclav Vetvicka、Sujata Saraswat-Ohri、Aruna Vashishta、Karine Descroix、Frank Jamois、Jean-Claude Yvin、Vincent Ferrières

  DOI：10.1016/j.carres.2011.06.020

  日期：2011.10

  (1 -> 3)-beta-D-Glucans are well-established natural biological immunomodulators. However, problems inherited with the natural origin of these polysaccharides bring about significant setbacks, including batch-to-batch heterogeneity and significant differences based on the source and isolation techniques. In this study, we tried to overcome these problems by preparation of a quantitatively new set of oligo-(1 -> 3)-beta-D-glucan-based synthetic immunomodulators. Some of these non-natural oligosaccharides showed biological activities, such as stimulation of phagocytosis, modulation of gene expression, and anti-cancer activity, which were superior to natural glucans. (C) 2011 Elsevier Ltd. All rights reserved.

  (1→3)-β-D-葡聚糖是公认的天然生物免疫调节剂。然而，这些多糖源于天然所带来的遗传问题，带来了重大挫折，包括批间异质性和基于来源及分离技术的显著差异。在这项研究中，我们试图通过制备一系列定量新的寡-（1→3)-β-D-葡聚糖基合成免疫调节剂来克服这些问题。其中一些非天然寡糖显示出生物活性，如刺激吞噬作用、调控基因表达和抗癌活性，这些活性优于天然葡聚糖。 © 2011 Elsevier Ltd. 保留所有权利。
• 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.