4-O-β-D-glucopyranosyl-D-mannose | 27452-49-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-β-D-glucopyranosyl-D-mannose
• 英文别名: 4-O-β-D-glucopyranosyl-D-mannopyranose；epicellobiose；beta-D-glucosyl-(1->4)-D-mannopyranose；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3S,4R,5S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 27452-49-9
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: GUBGYTABKSRVRQ-LNCRCTFVSA-N

物化性质

• 熔点：
  133-135 °C(Solv: methanol (67-56-1))
• 沸点：
  667.9±55.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  纤维素二糖 在 Ruminococcus albus cellobiose phosphorylase C₄₈₅A mutant 作用下， 以 aq. phosphate buffer 为溶剂， 反应 5.0h， 生成 4-O-β-D-glucopyranosyl-D-mannose
  参考文献：
  名称：

  Modulation of acceptor specificity of Ruminococcus albus cellobiose phosphorylase through site-directed mutagenesis

  摘要：

  Cellobiose phosphorylase (EC 2.4.1.20, CBP) catalyzes the reversible phosphorolysis of cellobiose to alpha-D-glucose 1-phosphate (Glc1P) and D-glucose. Cys485, Tyr648, and Glu653 of CBP from Ruminococcus albus, situated at the +1 subsite, were mutated to modulate acceptor specificity. C485A, Y648F, and Y648V were active enough for analysis. Their acceptor specificities were compared with the wild type based on the apparent kinetic parameters determined in the presence of 10 mM Glc1P. C485A showed higher preference for D-glucosamine than the wild type. Apparent k(cat)/K-m values of Y648F for D-mannose and 2-deoxy-D-glucose were 8.2- and 4.0-fold higher than those of the wild type, respectively. Y648V had synthetic activity toward N-acetyl-D-glucosamine, while the other variants did not. The oligosaccharide production in the presence of the same concentrations of wild type and each mutant was compared. C485A produced 4-O-beta-D-glucopyranosyl-D-glucosamine from 10 mM Glc1P and D-glucosamine at a rate similar to the wild type. Y648F and Y648V produced 4-O-beta-D-glucopyranosyl-D-mannose and 4-O-beta-D-glucopyranosyl-N-acetyl-D-glucosamine much more rapidly than the wild type when D-mannose and N-acetyl-D-glucosamine were used as acceptors, respectively. After a 4 h reaction, the amounts of 4-O-beta-D-glucopyranosyl-D-mannose and 4-O-beta-D-glucopyranosyl-N-acetyl-D-glucosamine produced by Y648F and Y648V were 5.9- and 12-fold higher than the wild type, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.06.010

文献信息

• Production of keto-disaccharides from aldo-disaccharides in subcritical aqueous ethanol
  作者：Da-Ming Gao、Takashi Kobayashi、Shuji Adachi

  DOI：10.1080/09168451.2015.1127135

  日期：2016.5.3

  Isomerization of disaccharides (maltose, isomaltose, cellobiose, lactose, melibiose, palatinose, sucrose, and trehalose) was investigated in subcritical aqueous ethanol. A marked increase in the isomerization of aldo-disaccharides to keto-disaccharides was noted and their hydrolytic reactions were suppressed with increasing ethanol concentration. Under any study condition, the maximum yield of keto-disaccharides produced from aldo-disaccharides linked by β-glycosidic bond was higher than that produced from aldo-disaccharides linked by α-glycosidic bond. Palatinose, a keto-disaccharide, mainly underwent decomposition rather than isomerization in subcritical water and subcritical aqueous ethanol. No isomerization was noted for the non-reducing disaccharides trehalose and sucrose. The rate constant of maltose to maltulose isomerization almost doubled by changing solvent from subcritical water to 80 wt% aqueous ethanol at 220 °C. Increased maltose monohydrate concentration in feed decreased the conversion of maltose and the maximum yield of maltulose, but increased the productivity of maltulose. The maximum productivity of maltulose was ca. 41 g/(h kg-solution).

  摘要：在亚临界水乙醇中研究了二糖（麦芽糖、异麦芽糖、赤霉糖、乳糖、甜菜碱、蔗糖和海藻糖）的异构化反应。注意到醛基二糖向酮基二糖的异构化明显增加，随着乙醇浓度的增加，它们的水解反应被抑制。在任何研究条件下，通过β-糖苷键连接的醛基二糖产生的酮基二糖的最大产量均高于通过α-糖苷键连接的醛基二糖产生的酮基二糖。在亚临界水和亚临界水乙醇中，酮基二糖甘露糖主要发生分解而非异构化。非还原性二糖海藻糖和蔗糖未观察到异构化。将溶剂从亚临界水改为80%乙醇水溶液后，麦芽糖向麦芽糖酮异构化的速率常数几乎翻倍，温度为220°C。在进料中增加麦芽糖单水合物浓度会降低麦芽糖的转化率和麦芽糖的最大产量，但会提高麦芽糖的生产率。麦芽糖的最大生产率约为41克/（小时·千克-溶液）。
• Efficient chemoenzymatic oligosaccharide synthesis by reverse phosphorolysis using cellobiose phosphorylase and cellodextrin phosphorylase from Clostridium thermocellum
  作者：Hiroyuki Nakai、Maher Abou Hachem、Bent O. Petersen、Yvonne Westphal、Karin Mannerstedt、Martin J. Baumann、Adiphol Dilokpimol、Henk A. Schols、Jens Ø. Duus、Birte Svensson

  DOI：10.1016/j.biochi.2010.07.013

  日期：2010.12

  Inverting cellobiose phosphorylase (CtCBP) and cellodextrin phosphorylase (CtCDP) from Clostridium thermocellum ATCC27405 of glycoside hydrolase family 94 catalysed reverse phosphorolysis to produce cellobiose and cellodextrins in 57% and 48% yield from α-d-glucose 1-phosphate as donor with glucose and cellobiose as acceptor, respectively. Use of α-d-glucosyl 1-fluoride as donor increased product yields

  糖苷水解酶家族94的热纤梭菌ATCC27405转化纤维二糖磷酸化酶（CtCBP）和纤维糊精磷酸化酶（CtCDP）催化逆向磷酸分解，以57％和48％的α-d-葡萄糖1-磷酸葡萄糖作为供体与葡萄糖和纤维素生成糊精。纤维二糖分别作为受体。使用α-d-葡萄糖基1-氟化物作为供体可将CtCBP的产品收率提高到98％，将CtCDP的收率提高到68％。CtCBP显示出广泛的受体特异性，可从五个单糖形成具有β-（1→4）-区域选择性的β-葡萄糖基二糖，以及从三个（1→6）连接的具有β-（1→4）-区域选择性的支链β-葡萄糖基三糖二糖。CtCDP表现出严格的β-（1→4）-区域选择性和催化的三个β-连接的葡糖基二糖，纤维二糖，槐糖和拉米纳糖的线性扩链，而12个测试的单糖不是受体。通过NMR和ESI-MS的结构分析证实了两个β-葡萄糖基寡糖产物系列代表了新化合物，即β-D-吡喃葡萄糖基-[（1→4）-β-D-吡喃葡萄糖基]（n）-（1→2）
• Identification of the Cellobiose 2-Epimerase Gene in the Genome of<i>Bacteroides fragilis</i>NCTC 9343
  作者：Takeshi SENOURA、Hidenori TAGUCHI、Shigeaki ITO、Shigeki HAMADA、Hirokazu MATSUI、Satoru FUKIYA、Atsushi YOKOTA、Jun WATANABE、Jun WASAKI、Susumu ITO

  DOI：10.1271/bbb.80691

  日期：2009.2.23

  Cellobiose 2-epimerase (CE, EC 5.1.3.11) catalyzes the reversible epimerization of cellobiose to 4-O-β-d-glucopyranosyl-d-mannose. In this study, we found a CE gene in the genome sequence of non-cellulolytic Bacteroides fragilis NCTC 9343. The recombinant enzyme, expressed in Escherichia coli cells, catalyzed a hydroxyl stereoisomerism at the C-2 positions of the reducing terminal glucose and at the mannose moiety of cello-oligosaccharides, lactose, β-mannobiose (4-O-β-d-mannopyranosyl-d-mannose), and globotriose [O-α-d-galactopyranosyl-(1→4)-O-β-d-galactopyranosyl-(1→4)-d-glucose]. The CE from B. fragilis showed less than 40% identity to reported functional CEs. It exhibited 44–63% identities to N-acyl-d-glucosamine 2-epimerase-like hypothetical proteins of unknown function in bacterial genome sequences of the phyla Firmicutes, Bacteroidetes, Proteobacteria, Chloroflexi, and Verrucomicrobia. On the other hand, it showed less than 26% identity to functional N-acyl-d-glucosamine 2-epimerases. Based on the amino acid homology and phylogenetic positions of the functional epimerases, we emphasize that many genes for putative N-acyl-d-glucosamine 2-epimerases and related hypothetical proteins of unknown function reported to date in the bacterial genomes should be annotated as CE-like proteins or putative CEs.

  纤维生物糖 2-表聚酶（CE，EC 5.1.3.11）催化纤维生物糖与 4-O-β-d-吡喃葡萄糖基-d-甘露糖的可逆表聚。在这项研究中，我们在非纤维素溶解性脆弱拟杆菌（Bacteroides fragilis NCTC 9343）的基因组序列中发现了一个 CE 基因。这种重组酶在大肠杆菌细胞中表达，可催化还原型末端葡萄糖的 C-2 位置和胞寡糖甘露糖分子的羟基立体异构、乳糖、β-甘露寡糖（4-O-β-d-甘露吡喃糖基-d-甘露糖）和球三糖[O-α-d-吡喃半乳糖基-(1→4)-O-β-d-吡喃半乳糖基-(1→4)-d-葡萄糖]。来自脆弱拟杆菌的 CE 与已报道的功能性 CE 的相同度低于 40%。它与固氮菌门、类杆菌门、变形菌门、绿僵菌门和疣菌门的细菌基因组序列中功能未知的 N-酰基-d-葡糖胺 2-epimerase-like假定蛋白的相同度为 44-63%。另一方面，它与功能性 N-acyl-d-glucosamine 2-epimerases 的同源性不足 26%。根据功能性表聚酶的氨基酸同源性和系统发育位置，我们强调迄今为止在细菌基因组中报道的许多假定的 N-酰基-d-葡糖胺 2-表聚酶基因和功能未知的相关假定蛋白应被注释为类 CE 蛋白或假定的 CEs。
• Polysaccharides ofEremurus. XV. Structure of the glucomannan ofEremurus lactiflorus
  作者：A. Dzhumamuratova、D. A. Rakhimov、E. S. Kondratenko

  DOI：10.1007/bf00579414

  日期：1982.11
• Polysaccharides ofPolygonatum. IV. A study of the structure of the glucomannan ofPolygonatum severzovii
  作者：R. K. Rakhmanberdyeva、D. A. Rakhimov、E. S. Kondratenko

  DOI：10.1007/bf00575033

  日期：1982.9