agarobiose | 5627-25-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: agarobiose
• 英文别名: (2S)-2-hydroxy-2-[(2S,3R,4S)-4-hydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]acetaldehyde
• CAS: 5627-25-8
• 化学式: C₁₂H₂₀O₁₀
• 分子量: 324.285
• InChiKey: JPLATTLXZFUKRQ-AWXGPMDLSA-N

物化性质

• 沸点：
  636.9±55.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)
• 溶解度：
  Soluble (water)

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  agarobiose 在 吡啶 、 盐酸 作用下， 以 水 为溶剂， 反应 20.0h， 生成 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,5-di-O-acetyl-3,6-anhydro-L-galactose diethyl dithioacetal
  参考文献：
  名称：

  Synthesis of peracetylated C-1-deoxyalditol- and C-glycoside-dipyrranes via dithioacetal derivatives

  摘要：

  Dipyrranes bearing peracetylated mono- or disaccharidic C-1-deoxyalditol moieties were prepared from D-galactose, c-glucose, c-mannose, and lactose. A partially hydrolyzed polysaccharide (agarose) was also used as starting material for the synthesis of a disaccharide-containing C-glycoside dipyrrane. These compounds were synthesized as follows: the sugar starting materials were first submitted to a mercaptolysis-acetylation one-pot procedure (EtSH/HCl-Ac2O/pyridine). The resulting peracetylated diethyl dithioacetals were converted into dipyrranes through carbonyl deprotection (H5IO6, THF-Et2O) followed by TFA-catalyzed pyrrole condensation with yields up to 62%. Overall yields from sugar starting materials were up to 49%. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.12.048
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 agarobiose
  参考文献：
  名称：

  Isolation of Agarobiose Derivative from the Mucilage of Gloiopeltis Furcata

  摘要：

  1. Gloiopeltis furcata 的黏液经过部分甲醇解作用，最终分离出甲基 d-半乳糖苷、3,6-脱水-l-半乳糖二甲基缩醛、甲基 d-木糖苷和琼脂二糖二甲基缩醛。2. 由于琼脂二糖衍生物获得了较好的产率，因此可以断定，该二糖代表了黏液分子的主要重复单元，前提是忽略黏液中存在的硫酸盐残基。3. 目前为止，木糖被首次确认与 Gloiopeltis 的黏液相关。但由于产率极低，该糖可能源自污染的木聚糖。

  DOI：

  10.1246/bcsj.31.428

文献信息

• Studies on the Chemical Constitution of Agar-agar. XIX. Pyruvic Acid as a Constituent of Agar-agar (Part 3). Structure of the Pyruvic Acid-linking Disaccharide Derivative Isolated from the Methanolysis Products of Agar
  作者：Susumu Hirase

  DOI：10.1246/bcsj.30.75

  日期：1957.1

  1. The structure of the acidic compound, isolated from the partial metha-nolysis products of agar in the previous work, has been investigated.2. Methylation data have indicated that the structure of the compound is 4-O-4′, 6′-O-1″-carboxyethylidene-β-d-galactopyranosyl-3,6-anhydro-l-galactose dimethyl-acetal, the β-linkage being suggested on the basis of the optical rotatory behavior.3. The structure assigned is also supported by the result of partial hydrolysis and periodate oxidation of the compound.4. No information has been obtained as to the configuration of the carbon atom C1 of the ethylidene group in the molecule.

  1. 在之前的研究中，从琼脂的部分甲醇解离产物中分离得到的酸性化合物的结构已经被研究。 2. 甲基化数据表明该化合物的结构为4-O-4′, 6′-O-1″-羧乙烯基-β-d-半乳糖吡喃糖-3,6-脱水-l-半乳糖二甲基缩醛，β-连接基因据光学旋转行为推测。 3. 所赋予的结构也得到了该化合物的部分水解和期亚硫酸盐氧化的结果支持。 4. 目前尚未获得关于分子中乙烯基团C1碳原子构型的信息。
• Production of carbohydrate building blocks from red seaweed polysaccharides. Efficient conversion of galactans into C-glycosyl aldehydes
  作者：Diogo R. B. Ducatti、Alessandro Massi、Miguel D. Noseda、Maria Eugênia R. Duarte、Alessandro Dondoni

  DOI：10.1039/b816606d

  日期：——

  and D-galactose, respectively) derivatives. Complete depolymerization of agarose and kappa-carrageenan under harsher conditions produced 3,6-anhydro L- and D-galactose aldehyde derivatives. Chain shortening of these products via alditol formation and oxidative carbon-carbon bond cleavage furnished C-formyl α-L- and α-D-threofuranosides. The above C-glycosyl aldehydes were all prepared on a meaningful

  琼脂和角叉菜胶是丰富的天然多糖，可通过以下方法大规模获得 水从各种红色海藻中提取。这些半乳聚糖，除了是制药和食品工业的有价值的产品外，还是低成本的原料，用于制备有用的和稀有的，基于碳水化合物的结构单元，这些单元很难通过全合成获得，而且价格昂贵。半合成L-和D-构象的两组C-糖基醛的半合成。琼脂糖分别描述了α-角叉菜胶和κ-角叉菜胶。简而言之，在温和条件下，两个半乳聚糖的部分酸催化巯基分解反应得到琼脂二糖 和角蛋白（β- d -Gal p - （1→4）-3,6-脱水-醛基-大号- 和 D-半乳糖）。完全解聚琼脂糖 和κ-角叉菜胶在更苛刻的条件下产生 3,6-脱水 L-和D-半乳糖醛衍生物。通过醛糖醇形成和氧化碳-碳键裂解提供的这些产品的链缩短C-甲酰基α- L-和α- D-呋喃呋喃糖苷。以上C-糖基醛均以克量的半乳聚糖为起始以有意义的制备规模制备。最终，通过Baeyer-Villiger氧化苄基化反应建立了一种新的制备2
• Biological upgrading of 3,6-anhydro-<scp>l</scp>-galactose from agarose to a new platform chemical
  作者：Dong Hyun Kim、Jing-Jing Liu、Jae Won Lee、Jeffrey G. Pelton、Eun Ju Yun、Sora Yu、Yong-Su Jin、Kyoung Heon Kim

  DOI：10.1039/c9gc04265b

  日期：——

  This study demonstrated the novel biological upgrading (using engineered yeast cells) of 3,6-anhydro-l-galactose, the main but untapped sugar of red macroalgal biomass, to 3,6-anhydro-l-galactitol that can be converted to various valuable chemicals including isosorbide.

  这项研究展示了一种新型的生物升级技术（使用工程酵母细胞），将红色大型藻类生物质中主要但未被利用的糖——3,6-脱水-l-半乳糖升级为3,6-脱水-l-半乳醇，后者可转化为各种有价值的化学品，包括异山梨醇。
• Matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry analysis of oligosaccharides and oligosaccharide alditols obtained by hydrolysis of agaroses and carrageenans, two important types of red seaweed polysaccharides
  作者：M.Kaniz Fatema、Hiroshi Nonami、Diogo R.B. Ducatti、Alan G. Gonçalves、M. Eugẻnia R. Duarte、Miguel D. Noseda、Alberto S. Cerezo、Rosa Erra-Balsells、María C. Matulewicz

  DOI：10.1016/j.carres.2009.10.009

  日期：2010.1

  oligosaccharide alditols derived from agaroses, kappa- and iota-carrageenans using different matrices (2,5-dihydroxybenzoic acid, nor-harmane, ferulic acid, and the ionic liquid matrices 2,5-dihydroxybenzoic acid-n-butylamine and ferulic acid-n-butylamine) were conducted. These carbohydrates were selected as model compounds to study the MALDI prompt and post-source decay (PSD) fragmentation processes of both

  MALDI-TOF质谱分析了使用不同基质（2,5-二羟基苯甲酸，去甲羟烷，阿魏酸和离子液体基质2，进行5-二羟基苯甲酸-正丁胺和阿魏酸-正丁胺。选择这些碳水化合物作为模型化合物，以研究两个寡糖家族的MALDI迅速和源后衰变（PSD）裂解过程。硫酸化糖醇以负离子模式显示为[M-Na]（-）的分子离子，以及通过其迅速裂解（主要是脱硫）而产生的物质，而硫酸化的低聚糖（醛糖）则主要表现出糖苷的即时裂解（糖苷C-裂解和脱硫）。非硫酸化醛糖和醛糖醇，只能以正离子模式（[M + Na]（+））进行分析，而没有任何迅速的破碎。前者在PSD模式下产生了交叉环碎片。对于所有研究的化合物，使用2,5-二羟基苯甲酸和/或正丁烷作为基质可获得最佳结果。
• Novel beta-agrase and microorganism generating the same
  申请人：KABUSHIKI KAISHA YAKULT HONSHA

  公开号：EP0743363A2

  公开（公告）日：1996-11-20

  Novel two types of β -agarases derived from a marine bacterium screened and isolated from marine sediment, include β -agarase A of a molecular weight of about 90,000 and β -agarase B of a molecular weight of about 98,000. β -agarase A has an enzyme activity of hydrolyzing agarose and porphyran mainly into neoagarotetraose and neoagaro hexaose. β -agarase B has an enzyme activity of hydrolyzing agarose and porphyran mainly into neoagarobiose. These novel two types of β -agarases are used for preparing an oligosaccharide and for preparing the protoplast of seaweed cells.

  从海洋沉积物中筛选和分离出的一种海洋细菌产生的两种新型β-琼脂糖酶，包括分子量约为 90,000 的β-琼脂糖酶 A 和分子量约为 98,000 的β-琼脂糖酶 B。β -琼脂糖酶 A 具有将琼脂糖和卟吩主要水解为新琼脂四糖和新琼脂六糖的酶活性。β -琼脂糖酶 B 具有将琼脂糖和卟吩主要水解成新琼脂生物糖的酶活性。这两种新型的 β -琼脂糖酶可用于制备寡糖和制备海藻细胞的原生质体。