3-O-(β-galactopyranosyl)-rac-glycerol | 7420-23-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 3-O-(β-galactopyranosyl)-rac-glycerol
• 英文别名: (2R,3R,4S,5R,6R)-2-(2,3-dihydroxypropoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 7420-23-7
• 化学式: C₉H₁₈O₈
• 分子量: 254.237
• InChiKey: NHJUPBDCSOGIKX-VGPGGAHRSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-O-(β-galactopyranosyl)-rac-glycerol 在 E. coli β-galactosidase 作用下， 以 水 为溶剂， 生成 口服葡萄糖 、 甘油
  参考文献：
  名称：

  Nakano, Hirofumi; Takenishi, Shigeyuki; Watanabe, Yasuto, Agricultural and Biological Chemistry, 1988, vol. 52, # 8, p. 1913 - 1922

  摘要：

  DOI：
• 作为产物：
  描述：

  (2'RS)-2',3'-epoxyprop-1'-yl-β-D-galactopyranoside 在 四乙基溴化铵 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 3-O-(β-galactopyranosyl)-rac-glycerol
  参考文献：
  名称：

  New enzyme catalyzed synthesis of monoacyl galactoglycerides

  摘要：

  DOI：

  10.1016/s0040-4020(88)90033-6

文献信息

• Prodrugs of a 3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives
  申请人：Sugen. Inc.

  公开号：US20030100555A1

  公开（公告）日：2003-05-29

  The present invention relates to pyrrole substituted 2-indolinone compounds and their pharmaceutically acceptable salts which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.

  本发明涉及吡咯替代的2-吲哚酮化合物及其药学上可接受的盐，这些化合物调节蛋白激酶的活性，因此预计在预防和治疗蛋白激酶相关的细胞疾病，如癌症方面具有用处。
• Enzymatic method for preparation of epoxy compounds
  申请人：NOVO NORDISK A/S

  公开号：EP0268461A2

  公开（公告）日：1988-05-25

  An epoxy group in a molecule can enzymatically be transferred to another molecule, thereby synthesising carbohydrates carrying an epoxy group in the aglycone position.

  分子中的环氧基团可以通过酶法转移到另一个分子上，从而合成在琼脂酮位置带有环氧基团的碳水化合物。
• PROCESS FOR PRODUCING GLYCOSIDES
  申请人：Showa Sangyo Co., Ltd.

  公开号：EP1205558A1

  公开（公告）日：2002-05-15

  The present invention provides a lactosyl glycoside or an N-acetyllactosaminyl glycoside useful as foods, functional food materials, medicines, and reagents with high yield and inexpensively by using a transfer reaction represented by the following formula in the presence of an enzyme having an activity of cleaving a β 1,4 glucosyl bond: LacA-X+Y → LacA-Y+X,   wherein LacA represents lactose or N-acetyllactosaminide; X represents hydrogen (H), a saccharide, a glycoconjugate, or a phenolic compound; and Y represents a compound having an alcoholic hydroxyl group or a phenolic hydroxyl group.

  本发明提供了一种乳糖基糖苷或 N-乙酰半乳糖酰胺基糖苷，在具有裂解 β 1,4 葡糖基键活性的酶存在下，通过下式表示的转移反应，可高产且廉价地用作食品、功能性食品材料、药物和试剂：LacA-X+Y→LacA-Y+X，其中 LacA 代表乳糖或 N-乙酰半乳糖酰胺；X 代表氢（H）、糖、糖苷或酚类化合物；Y 代表具有醇羟基或酚羟基的化合物。
• Synthesis of Glycosyl Glycerols and Related Glycolipids
  作者：René Suhr、Oliver Scheel、Joachim Thiem

  DOI：10.1080/07328309808007465

  日期：1998.8.1

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.
• Cross-utilization of β-galactosides and cellobiose in Geobacillus stearothermophilus
  作者：Smadar Shulami、Arie Zehavi、Valery Belakhov、Rachel Salama、Shifra Lansky、Timor Baasov、Gil Shoham、Yuval Shoham

  DOI：10.1074/jbc.ra120.014029

  日期：2020.7

  Strains of the Gram-positive, thermophilic bacteriumGeobacillus stearothermophiluspossess elaborate systems for the utilization of hemicellulolytic polysaccharides, including xylan, arabinan, and galactan. These systems have been studied extensively in strains T-1 and T-6, representing microbial models for the utilization of soil polysaccharides, and many of their components have been characterized both biochemically and structurally. Here, we characterized routes by whichG. stearothermophilusutilizes mono- and disaccharides such as galactose, cellobiose, lactose, and galactosyl-glycerol. TheG. stearothermophilusgenome encodes a phosphoenolpyruvate carbohydrate phosphotransferase system (PTS) for cellobiose. We found that the cellobiose-PTS system is induced by cellobiose and characterized the corresponding GH1 6-phospho-beta-glucosidase, Cel1A. The bacterium also possesses two transport systems for galactose, a galactose-PTS system and an ABC galactose transporter. The ABC galactose transport system is regulated by a three-component sensing system. We observed that both systems, the sensor and the transporter, utilize galactose-binding proteins that also bind glucose with the same affinity. We hypothesize that this allows the cell to control the flux of galactose into the cell in the presence of glucose. Unexpectedly, we discovered thatG. stearothermophilusT-1 can also utilize lactose and galactosyl-glycerol via the cellobiose-PTS system together with a bifunctional 6-phospho-beta-gal/glucosidase, Gan1D. Growth curves of strain T-1 growing in the presence of cellobiose, with either lactose or galactosyl-glycerol, revealed initially logarithmic growth on cellobiose and then linear growth supported by the additional sugars. We conclude that Gan1D allows the cell to utilize residual galactose-containing disaccharides, taking advantage of the promiscuity of the cellobiose-PTS system.