α-D-glucopyranosyl-(1→2)-[α-D-glucopyranosyl-(1→6)]-β-D-fructofuranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-glucopyranosyl-(1→2)-[α-D-glucopyranosyl-(1→6)]-β-D-fructofuranoside
• 英文别名: α-D-glucopyranosyl-(1->6)-β-fructofuranosyl-α-D-glucopyranoside；isomelezitose；2^Fru-α-Glcp-isomaltulose；6^Fru-α-Glcp-sucrose；Glc(a1-6)Fruf(b2-1a)Glc；(2S,3R,4S,5S,6R)-2-[[(2R,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: NIBVDXPSJBYJFT-HRUWSWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.8
• 重原子数：
  34
• 可旋转键数：
  8
• 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：

  Lactose 、 α-D-glucopyranosyl-(1→2)-[α-D-glucopyranosyl-(1→6)]-β-D-fructofuranoside 在 β-galactosidase from bovine testes EC 3.2.1.23 、 Na₂H₂PO₄*12H₂O 、 柠檬酸 作用下， 以 水 为溶剂， 反应 48.0h， 以23%的产率得到β-D-galactopyranosyl-(1->3)-α-D-glucopyranosyl-(1->6)-[α-D-glucopyranosyl-(1<->2)]-β-D-fructofuranoside
  参考文献：
  名称：

  利用牛睾丸中的β-半乳糖苷酶合成低聚糖作为潜在的新型食品成分并进行高级酶促反应

  摘要：

  牛睾丸的β-半乳糖苷酶（EC 3.2.1.23）促进半乳糖单元向歧管衍生物中的葡萄糖或含半乳糖的残基转移，从而建立β1→3键。

  DOI：

  10.1016/j.tet.2004.01.029
• 作为产物：
  描述：

  蔗糖 在 Leuconostoc mesenteroides NRRL B-1297 glucansucrase 作用下， 以 aq. acetate buffer 为溶剂， 生成 α-D-glucopyranosyl-(1→2)-[α-D-glucopyranosyl-(1→6)]-β-D-fructofuranoside
  参考文献：
  名称：

  葡聚糖形成异戊糖

  摘要：

  调查了几种葡聚糖的生产异甜糖的能力，这是一种结构为α-D-吡喃葡萄糖基（1→6）β-D-呋喃呋喃糖基（2→1）α-D-吡喃葡萄糖苷的三糖。除了一个例外，几乎所有测试的菌株至少产生痕量的异三聚糖。产率低但是显着，基于蔗糖，产率从小于1％到大约5％。该三糖可以以两种方式之一出现：将吡喃葡萄糖基转移到蔗糖的6Fru-OH位置，或转移到异麦芽酮糖的异头OH位置。这项研究表明异戊二糖的形成可能是许多葡糖苷酸酶反应的普遍现象。

  DOI：

  10.1016/j.carres.2017.01.004

文献信息

• Regioselective Synthesis of Galactosylated Tri- and Tetrasaccharides by Use of β-Galactosidase from<i>Bacillus circulans</i>
  作者：Joachim Thiem、Erzsébet Farkas、Ulja Schmidt、Jörg Kowalczyk、Markwart Kunz、Manfred Vogel

  DOI：10.1055/s-2003-38075

  日期：——

  forming β1→4 linkages. The synthesis of several biologically relevant tri- and tetrasaccharides β-D-Galp-(1→4)-β-D-Galp-(1→4)-α,β-D-Glcp (2), β-D-Galp-(1→4)-α-D-Glcp-(1→4)-D-Glcp-ol/Manp-ol (4), β-D-Galp-(1→4)-α-D-Glcp-(1→6)-β-D-Fruf (6), β-D-Galp-(1→4)-α-D-Glcp-(1↔2)-β-D-Fruf (8), β-D-Galp-(1→4)-α-D-Glcp-(1↔2)-β-D-Fruf-(1↔2)-β-D-Fruf (10), β-D-Galp-(1→4)-α-D-Glcp-(1→6)-[α-D-Glcp-(1↔2)]-β-D-Fruf (12a)

  来自环状芽孢杆菌的 β-半乳糖苷酶 (EC 3.2.1.23) 催化半乳糖单位向各种葡萄糖和半乳糖衍生物的转移，形成 β1→4 键。几种生物学相关的三糖和四糖的合成β-D-Galp-(1→4)-β-D-Galp-(1→4)-α,β-D-Glcp (2), β-D- Galp-(1→4)-α-D-Glcp-(1→4)-D-Glcp-ol/Manp-ol(4)、β-D-Galp-(1→4)-α-D-Glcp -(1→6)-β-D-Fruf (6), β-D-Galp-(1→4)-α-D-Glcp-(1↔2)-β-D-Fruf (8), β -D-Galp-(1→4)-α-D-Glcp-(1↔2)-β-D-Fruf-(1↔2)-β-D-Fruf (10), β-D-Galp- (1→4)-α-D-Glcp-(1→6)-[α-D-Glcp-(1↔2)]-β-D-Fruf (12a), β-D-Galp-(1→
• Mechanism-Oriented Redesign of an Isomaltulose Synthase to an Isomelezitose Synthase by Site-Directed Mutagenesis
  作者：Julian Görl、Malte Timm、Jürgen Seibel

  DOI：10.1002/cbic.201100576

  日期：2012.1.2

  The redesign of enzymes for new substrates and/or functions is a key endeavor of biocatalysis and the enzymatic synthesis of carbohydrates has been proven to be nontrivial in this regard. One single amino acid mutation, R333K, identified by mechanism‐oriented structural analysis, enabled us to generate an isomelezitose synthase out of the sucrose isomerase from Protaminobacter rubrum.

  针对新的底物和/或功能的酶的重新设计是生物催化的关键努力，并且碳水化合物的酶促合成在这方面已被证明是不平凡的。通过机制导向的结构分析鉴定出一个单一的氨基酸突变，R333K，使我们能够从来自红生棒杆菌的蔗糖异构酶中生成同聚半乳糖合酶。
• Hydrolysis of low-molecular-weight oligosaccharides and oligosaccharide alditols by pig intestinal sucrase/isomaltase and glucosidase/maltase
  作者：Sabine Hertel、Fritz Heinz、Manfred Vogel

  DOI：10.1016/s0008-6215(00)00008-2

  日期：2000.6

  The ability of purified pig intestinal sucrase/isomaltase (SI; EC 3.2.1.10/48) and glucosidase/maltase (GM; EC 3.2.1.20) to hydrolyze di- and oligosaccharides consisting of D-glucose and D-fructose residues and the corresponding alditols was studied. The products, after incubation, reflect different binding patterns at both catalytic sites of SI. The active site of the sucrase subunit cleaves alpha,beta-(1 --> 2) glycosidic bonds, and only two monomer units of the substrates bind with favorable affinity. Oligosaccharides and reduced oligosaccharides containing alpha-(1 --> 6) and alpha-(1 --> 1) glycosidic bonds are hydrolyzed by isomaltase, and for the active site of this subunit more than two subsites were postulated. Moreover, different binding sites for various aglycons seem to exist for isomaltase. Oligosaccharide alcohols are cleaved at lower rates if the reduced sugar residue occupies the aglycon binding site. GM also hydrolyzes alpha-(1 --> 1) linkages, but at a lower rate. The enzyme has the ability to bind compounds containing residues other than D-glucose. There are indications for similarities between GM and the isomaltase subunit of SI in the binding mode of oligosaccharides. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Lactose- and cellobiose-derived branched trisaccharides and a sucrose-containing trisaccharide produced by acceptor reactions of Weissella confusa dextransucrase
  作者：Qiao Shi、Minna Juvonen、Yaxi Hou、Ilkka Kajala、Antti Nyyssölä、Ndegwa Henry Maina、Hannu Maaheimo、Liisa Virkki、Maija Tenkanen

  DOI：10.1016/j.foodchem.2015.05.090

  日期：2016.1

  Dextran-producing Weissella have received significant attention. However, except for maltose, the acceptor reactions of Weissella dextransucrases with different sugars have not been investigated. The action of recombinant Weissella confuse VIT E-90392 dextransucrase was tested with several potential acceptors, particularly, analogs lactose and cellobiose. The major acceptor products of both disaccharides were identified as branched trisaccharides, with a glucosyl residue alpha-(1 -> 2)-linked to the acceptor's reducing end. An additional product, isomelezitose (6(Fru)-alpha-Glcp-sucrose), was also produced when using lactose as an acceptor. This is the first report of the synthesis of isomelezitose by a dextransucrase. The NMR spectra of the three trisaccharides were fully assigned, and their structures were confirmed by selective enzymatic hydrolysis. The trisaccharides prepared from C-13(6)glc sucrose and lactose were analyzed by ESI-MSn, and the fragmentation patterns of these compounds were characterized. (C) 2015 Elsevier Ltd. All rights reserved.
• Sucrosyl‐(1 → 2)‐β‐Isomaltulose: Enzymatic Synthesis and Structure Determination
  作者：Sonja Ehrhardt、Frank Rittig、Manfred Vogel、Victor Wray、Bernhard Skeries

  DOI：10.1081/car-120037574

  日期：2004.12.26

  By enzymatic reaction of sucrose (1) and isomelezitose (2) with the enzyme inulinase (NOVO, SP230) a novel tetrasaccharide (3) was synthesised,.the molecular weight of which was confirmed by electrospray-ionisation mass spectrometry and gel permeation chromatography. Its structure was established by acid hydrolysis as well as H-1 and C-13 NMR spectroscopy to be sucrosyl-(1-->2)-beta-isomaltulose 3 (alpha-D-glucopyranosyl-(1-->2)-beta-D-fructofuranosyl-(1-->2)-beta-D-fructofuranosyl-(6-->1)-alpha-D-glucopyranoside).