D-lactose | 15761-61-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: D-lactose
• 英文别名: β-D-glucosyl-(1→4)-D-mannose；O⁴-β-D-Glucopyranosyl-D-mannose；4-O-β-glucosyl-D-mannose；4-O-β-D-glucopyranosyl-D-mannose；4-O-beta-D-Glucopyranosyl-D-mannose；(2S,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanal
• CAS: 15761-61-2
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: DKXNBNKWCZZMJT-VOXHDCLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  197
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  吲哚 、 D-lactose 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙醇 、 水 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  Direct C-glycosylation of indole with unprotected mono-, di-, and trisaccharides: a one-pot synthesis of 1-deoxy-1,1-bis(3-indolyl)alditols

  摘要：

  1-Deoxy-1, 1-bis(3-indolyl)alditols were synthesized by reacting 2.5 equiv of indole with 1 equiv of the following seven monosaccharides (D-galactose, D-mannose, D-allose, 2-deoxy-D-arabinohexose (2-deoxy-D-glucose), D-arabinose, L-arabinose, D-xylose), two disaccharides (D-lactose, D-maltose), and a trisaccharide (D-maltotriose) in 1:1 EtOH-H(2)O at room temperature, or at 40 or 50 degrees C, in the presence of 5 mol % scandium(III) trifluoromethanesulfonate [Sc(OTf)(3)], in a one-pot reaction, in 36-95% yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.08.018
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 过氧化氢苯甲酰 、 乙醚 作用下， 生成 D-lactose
  参考文献：
  名称：

  Haworth et al., Journal of the Chemical Society, 1930, p. 2636,2638

  摘要：

  DOI：

文献信息

• Converting Galactose into the Rare Sugar Talose with Cellobiose 2-Epimerase as Biocatalyst
  作者：Stevie Van Overtveldt、Ophelia Gevaert、Martijn Cherlet、Koen Beerens、Tom Desmet

  DOI：10.3390/molecules23102519

  日期：——

  from d-galactose was discovered, a reaction not yet known to occur in nature. Moreover, the conversion is industrially relevant, as talose and its derivatives have been reported to possess important antimicrobial and anti-inflammatory properties. As the enzyme also catalyzes the keto-aldo isomerization of galactose to tagatose as a minor side reaction, the purity of talose was found to decrease over time

  来自 Rhodothermus marinus (RmCE) 的纤维二糖 2-差向异构酶在 β-1,4 连接的寡糖的还原端可逆地将葡萄糖残基转化为甘露糖残基。在这项研究中，已经绘制了 RmCE 的单糖特异性，并发现了从 d-半乳糖合成 d-塔糖，这种反应尚未在自然界中发生。此外，该转化具有工业相关性，因为据报道，塔罗糖及其衍生物具有重要的抗菌和抗炎特性。由于该酶还催化半乳糖酮醛异构化为塔格糖作为次要副反应，因此发现塔糖的纯度随着时间的推移而降低。经过工艺优化，可以得到23 g/L的塔糖，产品纯度为86%，产率为8.5%（从4 g（24 mmol）半乳糖开始）。然而，分别通过减少和增加反应时间可以达到更高的纯度和浓度。此外，还进行了两次工程尝试。首先，创建了一个 RmCE 突变文库，以尝试增加对单糖底物的活性。接下来，将来自 RmCE 的两个残基引入来自 Caldicellulosiruptor
• Functional reassignment of <i>Cellvibrio vulgaris</i> EpiA to cellobiose 2-epimerase and an evaluation of the biochemical functions of the 4-<i>O</i>-β-<scp>d</scp>-mannosyl-<scp>d</scp>-glucose phosphorylase-like protein, UnkA
  作者：Wataru Saburi、Yuka Tanaka、Hirohiko Muto、Sota Inoue、Rei Odaka、Mamoru Nishimoto、Motomitsu Kitaoka、Haruhide Mori

  DOI：10.1080/09168451.2015.1012146

  日期：2015.6.3

  The aerobic soil bacterium Cellvibrio vulgaris has a β-mannan-degradation gene cluster, including unkA, epiA, man5A, and aga27A. Among these genes, epiA has been assigned to encode an epimerase for converting d-mannose to d-glucose, even though the amino acid sequence of EpiA is similar to that of cellobiose 2-epimerases (CEs). UnkA, whose function currently remains unknown, shows a high sequence identity to 4-O-β-d-mannosyl-d-glucose phosphorylase. In this study, we have investigated CE activity of EpiA and the general characteristics of UnkA using recombinant proteins from Escherichia coli. Recombinant EpiA catalyzed the epimerization of the 2-OH group of sugar residue at the reducing end of cellobiose, lactose, and β-(1→4)-mannobiose in a similar manner to other CEs. Furthermore, the reaction efficiency of EpiA for β-(1→4)-mannobiose was 5.5 × 104-fold higher than it was for d-mannose. Recombinant UnkA phosphorolyzed β-d-mannosyl-(1→4)-d-glucose and specifically utilized d-glucose as an acceptor in the reverse reaction, which indicated that UnkA is a typical 4-O-β-d-mannosyl-d-glucose phosphorylase.

  摘要：有氧土壤细菌Cellvibrio vulgaris具有一个β-甘露聚糖降解基因簇，包括unkA、epiA、man5A和aga27A。在这些基因中，epiA被指定为编码一个使d-甘露糖转化为d-葡萄糖的异构酶，尽管EpiA的氨基酸序列与赤霉糖2-异构酶（CEs）的相似。UnkA的功能目前仍未知，显示出与4-O-β-d-甘露基-d-葡萄糖磷酸化酶具有高度相似的序列。在这项研究中，我们使用大肠杆菌的重组蛋白研究了EpiA的CE活性和UnkA的一般特性。重组EpiA催化了赤霉糖、乳糖和β-(1→4)-甘露二糖末端的糖残基的2-OH基的异构化，类似于其他CEs。此外，EpiA对β-(1→4)-甘露二糖的反应效率比对d-甘露高5.5×104倍。重组UnkA对β-d-甘露基-(1→4)-d-葡萄糖进行了磷酸解除作用，并在反向反应中特异地利用d-葡萄糖作为受体，这表明UnkA是一种典型的4-O-β-d-甘露基-d-葡萄糖磷酸化酶。
• Biochemical Characterization of a Thermophilic Cellobiose 2-Epimerase from a Thermohalophilic Bacterium,<i>Rhodothermus marinus</i>JCM9785
  作者：Teruyo OJIMA、Wataru SABURI、Hiroki SATO、Takeshi YAMAMOTO、Haruhide MORI、Hirokazu MATSUI

  DOI：10.1271/bbb.110456

  日期：2011.11.23

  Cellobiose 2-epimerase (CE) reversibly converts glucose residue to mannose residue at the reducing end of β-1,4-linked oligosaccharides. It efficiently produces epilactose carrying prebiotic properties from lactose, but the utilization of known CEs is limited due to thermolability. We focused on thermoholophilic Rhodothermus marinus JCM9785 as a CE producer, since a CE-like gene was found in the genome of R. marinus DSM4252. CE activity was detected in the cell extract of R. marinus JCM9785. The deduced amino acid sequence of the CE gene from R. marinus JCM9785 (RmCE) was 94.2% identical to that from R. marinus DSM4252. The N-terminal amino acid sequence and tryptic peptide masses of the native enzyme matched those of RmCE. The recombinant RmCE was most active at 80 °C at pH 6.3, and stable in a range of pH 3.2–10.8 and below 80 °C. In contrast to other CEs, RmCE demonstrated higher preference for lactose over cellobiose.

  Cellobiose 2-epimerase（CE）可逆地将β-1,4-连接寡糖还原端的葡萄糖残基转化为甘露糖残基。它能有效地从乳糖中产生具有益生特性的表乳糖，但由于热稳定性的原因，对已知 CE 的利用受到了限制。由于在R. marinus DSM4252的基因组中发现了一个类似CE的基因，因此我们重点研究了嗜热型Rhodothermus marinus JCM9785作为CE生产者的情况。在 R. marinus JCM9785 的细胞提取物中检测到了 CE 活性。R. marinus JCM9785的CE基因（RmCE）的氨基酸序列与R. marinus DSM4252的氨基酸序列有94.2%的相同度。原生酶的 N 端氨基酸序列和胰蛋白酶肽的质量与 RmCE 相吻合。重组的 RmCE 在 pH 值为 6.3、温度为 80 ℃ 时活性最高，在 pH 值为 3.2-10.8 和低于 80 ℃ 的范围内稳定。与其他 CE 相比，RmCE 对乳糖的偏好高于纤维生物糖。
• CELLOBIOSE 2-EPIMERASE, ITS PREPARATION AND USES
  申请人：Watanabe Hikaru

  公开号：US20120040407A1

  公开（公告）日：2012-02-16

  The present invention has objects to provide a thermostable cellobiose 2-epimerase, its preparation and uses. The present invention attains the above objects by providing a thermostable cellobiose 2-epimerase, a DNA encoding the enzyme, a recombinant DNA and transformant comprising the DNA, a process for producing the enzyme, and a process for producing isomerized saccharides using the enzyme.

  本发明的目的是提供一种热稳定的纤维二糖2-表异构酶，其制备和用途。本发明通过提供一种热稳定的纤维二糖2-表异构酶，编码该酶的DNA，含有该DNA的重组DNA和转化体，生产该酶的过程以及使用该酶生产异构化糖的过程来实现上述目的。
• PREBIOTIC COMPOSITIONS COMPRISING OLIGOSACCHARIDES FROM HYPTIS SUAVEOLENS
  申请人：Sinutron KG

  公开号：EP3275446A1

  公开（公告）日：2018-01-31

  Disclosed is a prebiotic composition comprising one or more oligosaccharides, selected from the group consisting of - a βGlc-(1→4) [βGal-(1→2)-α-Gal-(1→6)] Man tetrasaccharide, - a nonasaccharide consisting of a Glc(1→ ) βMan(1→4)βGlc(1→4)[βGal (1→2)αGal(1→6)]Man hexasaccharide with three βGal monosaccharide residues attached as branches to the hexasaccharide, and - higher oligosaccharides (degree of polymerization 9 - 13), typically consisting of a Glc(1→) Glc(1→) Glc(1→) βMan(1→4)βGlc(1→4) [βGal(1→2)αGal(1→6)]Man with three or more β-Gal monosaccharide residues attached as branches to the octasaccharide, wherein the tetrasaccharide and/or the nonasaccharide and/or the higher oligosaccharides is/are contained in the composition in an amount of at least 5 % w/w, preferably at least 10 % w/w, especially at least 25 % w/w, dry weight.

  本发明公开了一种益生元组合物，该组合物包含一种或多种低聚糖，这些低聚糖选自以下组别 - βGlc-(1→4)[βGal-(1→2)-α-Gal-(1→6)] Man 四糖、 - 由 Glc(1→ ) βMan(1→4)βGlc(1→4)[βGal(1→2)αGal(1→6)]Man 六糖和作为六糖分支连接的三个 βGal 单糖残基组成的非糖，以及 - 更高的寡糖（聚合度为 9 - 13），通常由 Glc(1→) Glc(1→) Glc(1→) βMan(1→4)βGlc(1→4) [βGal(1→2)αGal(1→6)]Man 组成，其中有三个或更多的β-Gal 单糖残基作为分支连接到八糖上、 其中四糖和/或非糖和/或高级低聚糖在组合物中的含量至少为 5%（重量比），最好至少为 10%（重量比），特别是至少为 25%（重量比）（干重）。