O-β-D-galactopyranosyl (1-4)-D-xylose | 159702-00-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-β-D-galactopyranosyl (1-4)-D-xylose
• 英文别名: β-D-galactopyranosyl-(1,4)-D-xylose；4-O-β-D-galactopyranosyl-D-xylose；Gaxilosa；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(3R,4R,5R)-4,5,6-trihydroxyoxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 159702-00-8
• 化学式: C₁₁H₂₀O₁₀
• 分子量: 312.274
• InChiKey: VCTBNHVCBSUQPG-NCRZSTDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  D-吡喃木糖 在 palladium on activated charcoal β-galactosidase from E. coli 、 氢气 、 溶剂黄146 作用下， 以 acidic aq. solution 、 phosphate buffer 、 乙醇 为溶剂， 20.0~50.0 ℃ 、6.0 MPa 条件下， 反应 29.0h， 生成 O-β-D-galactopyranosyl (1-4)-D-xylose
  参考文献：
  名称：

  Regiospecific synthesis of lactose analog Gal-(β 1,4)-Xyl by transgalactosylation

  摘要：

  已开发出一种合成二糖4-O-β-D-半乳糖基-D-木糖（1）的短酶法合成方法，这对于作为乳糖不耐症的非侵入性药物检测的乳糖类似物具有兴趣。起始物质苄基α-D-木糖苷是通过D-木糖与苄醇的Fischer型糖苷化反应获得的，随后使用来自大米曲霉的一种糖苷酶对混合糖苷进行异构差异化。从几种商业β-半乳糖苷酶中筛选出具有转半乳糖化能力的酶，发现大肠杆菌的酶能够催化供体化合物o-硝基苯基β-D-半乳糖苷或乳糖向α-D-木糖苷的几乎区域和立体特异性的半乳糖基转移。随后的氢解脱保护反应产生所需的二糖1。关键词：寡糖合成，β-半乳糖苷酶，乳糖不耐症。

  DOI：

  10.1139/v02-106

文献信息

• Optimizing the enzymatic synthesis of β-d-galactopyranosyl-d-xyloses for their use in the evaluation of lactase activity in vivo
  作者：Carmen Hermida、Guillermo Corrales、Francisco J. Cañada、Juan J. Aragón、Alfonso Fernández-Mayoralas

  DOI：10.1016/j.bmc.2007.04.067

  日期：2007.7

  their use in the evaluation of intestinal lactase activity in vivo. Their administration to suckling rats followed by determination of the derived D-xylose in the urine and measurement of lactase activity in intestinal homogenates showed 1 to be the most suitable disaccharide for a potential test of the deficiency of intestinal lactase. The synthesis of 1 was further studied by evaluating the effect of

  通过β-半乳糖苷酶催化反应获得二糖2-O-，3-O-和4-O-β-D-吡喃半乳糖基-D-木糖（分别为2、3和1），以用于评估体内肠道乳糖酶活性的测定。他们对乳鼠的给药，然后测定尿液中衍生的D-木糖，并测量肠匀浆中的乳糖酶活性，结果表明1是最适合用于检测肠道乳糖酶缺乏症的二糖。通过评估不同变量对酶促半乳糖基化反应的收率和区域选择性的影响，进一步研究了1的合成，并优化了纯化工艺。
• Regioselectivity of the enzymatic transgalactosidation of d- and l-xylose catalysed by β-galactosidases
  作者：Esther Montero、Jose Alonso、Francisco J. Cañada、Alfonso Fernández-Mayoralas、Manuel Martín-Lomas

  DOI：10.1016/s0008-6215(97)10002-7

  日期：1997.12

  The regioselectivity of enzymatic transgalactosidation depends on the source of the beta-galactosidase used. When the galactosyl acceptor only contains secondary hydroxyl groups, e.g., D- or L-xylose, it is possible to find an enzyme that catalyses preferentially the synthesis of any of the three regioisomers 4-, 3- and 2-O-beta-D-galactopyranosyl-D-xylose (1, 2 and 3, respectively) or 4-, 3- and

  酶促半乳糖苷化的区域选择性取决于所用β-半乳糖苷酶的来源。当半乳糖基受体仅包含仲羟基，例如D-或L-木糖时，有可能找到一种酶，优先催化三种区域异构体4-，3-和2-O-β-D的合成-半乳糖吡喃糖基-D-木糖（分别为1、2和3）或4-，3-和2-O-β-D-吡喃半乳糖苷-L-木糖（分别为4、5和6）。通过O-硝基苯基-β-D-D-半乳糖吡喃糖苷和D-木糖的半乳糖苷化反应，分别使用来自大肠杆菌，牛睾丸或米曲霉的β-半乳糖苷酶获得1、2或3中的富集混合物，并在4、4中富集混合物使用米曲霉的β-半乳糖苷酶以类似方式获得5或6，
• A novel cold-active β-d-galactosidase with transglycosylation activity from the Antarctic Arthrobacter sp. 32cB – Gene cloning, purification and characterization
  作者：Anna Pawlak-Szukalska、Marta Wanarska、Arkadiusz Tomasz Popinigis、Józef Kur

  DOI：10.1016/j.procbio.2014.09.018

  日期：2014.12

  A gene encoding a novel beta-D-galactosidase from the psychrotolerant Antarctic bacterium Arthrobacter sp. 32cB was isolated, cloned and expressed in Escherichia coli. The active form of recombinant beta-D-galactosidase consists of two subunits with a combined molecular weight of approximately 257 kDa. The enzyme's maximum activity towards o-nitrophenyl-beta-D-galactopyranoside was determined as occurring at 28 degrees C and pH 8.0. However, it exhibited 42% of maximum activity at 10 degrees C and was capable of hydrolyzing both lactose and o-nitrophenyl-beta-D-galactopyranoside at that temperature, with K-m, values of 1.52 and 16.56 mM, and k(cat) values 30.55 and 31.84 s(-1), respectively. Two units of the enzyme hydrolyzed 90% of the lactose in 1 mL of milk at 10 degrees C in 24 h. The transglycosylation activity of Arthrobacter sp. 32cB beta-D-galactosidase was also examined. It synthesized galactooligosaccharides in a temperature range from 10 to 30 degrees C. Moreover, it catalyzed the synthesis of heterooligosaccharides such as lactulose, galactosyl-xylose and galactosyl-arabinose, alkyl glycosides, and glycosylated salicin from lactose and the appropriate acceptor at 30 degrees C. The properties of Arthrobacter sp. 32cB beta-D-galactosidase make it a candidate for use in the industrial removal of lactose from milk and a promising tool for the glycosylation of various acceptors, especially those which are thermosensitive. (C) 2014 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY-NC-ND license.
• Enzymatic syntheses and selective hydrolysis of O-β-d-galactopyranosides using a marine mollusc β-galactosidase
  作者：Assunta Giordano、Annabella Tramice、Giuseppina Andreotti、Ernesto Mollo、Antonio Trincone

  DOI：10.1016/j.bmcl.2004.10.016

  日期：2005.1

  The use of crude extract of the hepatopancreas of Aplysia fasciata, a large mollusc belonging to the order Anaspidea containing a beta-galactosidase activity, was reported for the synthesis of different galactosides. Good yields with polar acceptors and the uncommon beta-1-3 selectivity in the transgalactosylation reactions with most of the acceptors were observed. A beta-1-2 selectivity in the hydrolytic conditions was also observed and discussed. (C) 2004 Elsevier Ltd. All rights reserved.
• ENZYMATIC METHOD FOR THE EVALUATION OF XYLOSE
  申请人：Venter Pharma, S.L

  公开号：EP3394284B1

  公开（公告）日：2020-02-12