UDP-Gal

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: UDP-Gal
• 英文别名: uridine 5'-diphosphogalactose disodium salt；sodium;[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-oxidophosphoryl] [(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate
• 化学式: C₁₅H₂₂N₂O₁₇P₂*2Na
• 分子量: 610.27
• InChiKey: DUAFLAJOJQGVNQ-HRRBYNKCSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -9.05
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  302.65
• 氢给体数：
  7.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  UDP-Gal 在 pyruvate kinase 、 3,3,3-膦三基三丙酸 、 磷烯醇丙酮酸 、 还原型辅酶Ⅰ 、 magnesium chloride 、 L-lactate dehydrogenase 作用下， 以 aq. buffer 为溶剂， 反应 0.17h， 生成 尿苷-5’-二磷酸
  参考文献：
  名称：

  The Glycosyltransferase Involved in Thurandacin Biosynthesis Catalyzes Both O- and S-Glycosylation

  摘要：

  The S-glycosyltransferase SunS is a recently discovered enzyme that selectively catalyzes the conjugation of carbohydrates to the cysteine thiol of proteins. This study reports the discovery of a second S-glycosyltransferase, ThuS, and shows that ThuS catalyzes both S-glycosylation of the thiol of cysteine and O-glycosylation of the hydroxyl group of serine in peptide substrates. ThuS-catalyzed S-glycosylation is more efficient than O-glycosylation, and the enzyme demonstrates high tolerance with respect to both nucleotide sugars and peptide substrates. The biosynthesis of the putative products of the thuS gene cluster was reconstituted in vitro, and the resulting S-glycosylated peptides thurandacin A and B exhibit highly selective antimicrobial activity toward Bacillus thuringiensis.

  DOI：

  10.1021/ja411159k
• 作为产物：
  描述：

  uridine 5'-triphosphate trisodium salt 、 galactose-α-1-phosphate barium salt 在 sodium,[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl [hydroxy-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphoryl] phosphate 作用下， 以43%的产率得到UDP-Gal
  参考文献：
  名称：

  Practical enzyme-based syntheses of uridine 5'-diphosphogalactose and uridine 5'-diphospho-N-acetylgalactosamine on a gram scale

  摘要：

  Practical enzyme-based routes for the syntheses of uridine 5'-diphosphogalactose (UDP-Gal) and uridine 5'-diphospho-N-acetylgalactosamine (UDP-GalNAc) on millimole scales have been developed. The activity of galactokinase (EC 2.7.1.6) in crude enzyme extracts from galactose-adapted yeast, coupled to a regenerating system for ATP, provides convenient and economical access to galactose-alpha-1-phosphate (Gal-1-P) and galactosamine-alpha-1-phosphate (GalN-1-P). The transfer of UMP to the sugar-1-phosphates was also accomplished enzymatically by Gal-1-P uridyltransferase (EC 2.7.7.12) using uridine 5'-diphosphoglucose (UDP-Glc) as the UMP donor. UDP-Glc was in turn regenerated in situ from glucose-1-phosphate and UTP using UDP-Glc pyrophosphorylase (EC 2.7.7.9). The only chemical step in the sequence was the acetylation of UDP-GalN to afford UDP-GalNAc using N-acetoxysuccinimide. The moderate overall yields (43% and 34% for UDP-Gal and UDP-GalNAc from Gal-1-P and GalN-1-P, respectively) were compensated by the straightforward preparation of the starting materials, UTP and the corresponding sugar-1-P.

  DOI：

  10.1021/jo00027a029

文献信息

• Enzymatic Synthesis of 2-(β-Galactosyl)-ethyl Methacrylate by β-Galactosidase from <i>Pyrococcus woesei</i> and Application for Glycopolymer Synthesis and Lectin Studies
  作者：Marius Hoffmann、Elisabeth Gau、Susanne Braun、Andrij Pich、Lothar Elling

  DOI：10.1021/acs.biomac.9b01647

  日期：2020.2.10

  for the synthesis of glycosides by transglycosylation reactions. Especially glycosidases from hyperthermophilic bacteria are useful for reactions under extreme reaction conditions, e.g., in the presence of organic solvents. We herein report the facile enzymatic synthesis and purification of 2-(β-galactosyl)-ethyl methacrylate (Gal-EMA) with the recombinant hyperthermostable glycosidase from Pyrococcus

  糖苷酶长期以来一直用于通过转糖基化反应合成糖苷。特别是来自嗜热细菌的糖苷酶可用于极端反应条件下的反应，例如在有机溶剂的存在下。我们在此报道了以高产率从重组火球菌得到的2-（β-半乳糖基）-甲基丙烯酸乙酯（Gal-EMA）的简便酶促合成和纯化。优化的反应条件导致了半乳糖基化单体的克级合成，转糖基化率为88％。Gal-EMA产物的特征在于高效液相色谱-电喷雾电离质谱（HPLC-ESI-MS），核磁共振（NMR）光谱和红外（IR）光谱。Gal-EMA用于合成糖官能化的丙烯酸酯聚合物，其中掺入了一定量的半乳糖（0-100％）。使用酶联凝集素测定（ELLA）分析来自蓖麻的凝集素RCA120与糖聚合物的结合亲和力，发现KD值介于0.24和6.2 nM之间，具体取决于掺入的Gal-EMA的量。Gal-EMA合成丙烯酸酯官能化的聚糖低聚物的潜力已通过两个糖基转移酶顺序延长末端半乳糖而得到证实，从而产生了末
• Three-Dimensional Arrays Using GlycoPEG Tags: Glycan Synthesis, Purification and Immobilisation
  作者：Juan Etxebarria、Sonia Serna、Ana Beloqui、Manuel Martin-Lomas、Niels-Christian Reichardt

  DOI：10.1002/chem.201204004

  日期：2013.4.8

  bifunctional polyethyleneglycol (PEG) tags, extended enzymatically with the help of recombinant glycosyltransferases and finally purified by ultrafiltration. When printed directly onto activated glass slides, these glycoPEG tags afforded arrays with exceptionally high sensitivity, low background and excellent spot morphology. Likewise, the conjugation of glycoPEG tags to latex nanoparticles yielded multivalent

  聚糖阵列已成为快速建立凝集素和碳水化合物加工酶结合或底物特异性的主要工具。需要新的方法来加速碳水化合物的合成以解决天然聚糖结构的巨大复杂性。此外，优化聚糖固定化是开发选择性，灵敏和可重现的基于阵列的检测方法的关键。我们提出了一种基于标签的方法，可通过改善寡糖的合成，纯化和固定化来加速所有水平的聚糖阵列的制备。将聚糖引物化学连接至双功能聚乙二醇（PEG）标签，借助重组糖基转移酶进行酶促延伸，最后通过超滤纯化。当直接在激活的载玻片上打印时，这些glycoPEG标签为阵列提供了极高的灵敏度，低背景和出色的斑点形态。同样，糖PEG标签与乳胶纳米颗粒的缀合产生了用于碳水化合物结合测定的多价支架，具有非常低的非特异性结合。
• Construction and Structural Characterization of Versatile Lactosaminoglycan-Related Compound Library for the Synthesis of Complex Glycopeptides and Glycosphingolipids
  作者：Kentarou Naruchi、Tomoki Hamamoto、Masaki Kurogochi、Hiroshi Hinou、Hiroki Shimizu、Takahiko Matsushita、Naoki Fujitani、Hirosato Kondo、Shin-Ichiro Nishimura

  DOI：10.1021/jo0617161

  日期：2006.12.1

  We have established a facile and efficient protocol for the preparative-scale synthesis of various compound libraries related to lactosaminoglycans: cell surface oligosaccharides composed of N-acetyllactosamine as a repeating disaccharide unit, based on chemical and enzymatic approaches. Substrate specificity and feasibility of a bacterial glycosyltransferase, Neisseria meningitidis β1,3-N-acetylg

  我们已经建立了一种简便有效的方案，用于制备规模化合成与乳糖胺聚糖有关的各种化合物文库：基于化学和酶促方法，由N-乙酰基乳糖胺作为重复的二糖单元组成的细胞表面寡糖。底物特异性和细菌糖基转移酶的可行性，奈瑟氏脑膜炎β1,3- Ñ -acetylglucosaminyltransferase（LgtA），为了合成适合于哺乳动物的构造各种关键中间体进行了调查ö -glycopeptides和鞘糖脂含聚Ñ-乙酰基乳糖胺结构。重组LgtA在强碱性条件（pH = 10，甘氨酸-NaOH缓冲液）和20至30°C的最佳温度范围内表现出最高的糖基转移酶活性。有趣的是，我们发现LgtA判别升丝氨酸和升-苏氨酸和既用作核心-1β1,3- Ñ -acetylglucosaminyltransferase和芯2β1,3- Ñ朝向的Fmoc-SER衍生物-acetylglucosaminyltransferase，而LgtA显示仅核心2β1
• Membrane-Bound Stable Glycosyltransferases: Highly Oriented Protein Immobilization by a C-Terminal Cationic Amphipathic Peptide
  作者：Kentaro Naruchi、Shin-Ichiro Nishimura

  DOI：10.1002/anie.201007153

  日期：2011.2.7

  Turning tail: The specific functions of C‐terminal cationic amphipathic peptide in the formation of bacterial membrane‐bound glycosyltransferases have been demonstrated. This mechanism was applied to a general concept that allows highly oriented immobilization of enzymes on membrane‐mimetic solid surfaces, such as recombinant full‐length H. pylori α1,3‐fucosyltransferase on a magnetic bead (see picture)

  转弯：已经证明了C末端阳离子两亲性肽在细菌膜结合糖基转移酶形成中的特定功能。该机制适用于允许将酶高度定向固定在膜模拟固体表面上的一般概念，例如将重组全长幽门螺杆菌α1,3-岩藻糖基转移酶固定在磁珠上（参见图片）。
• Chemo-Enzymatic Synthesis of Branched<i>N</i>-Acetyllactosamine Glycan Oligomers for Galectin-3 Inhibition
  作者：Dominic Laaf、Hanna Steffens、Helena Pelantová、Pavla Bojarová、Vladimír Křen、Lothar Elling

  DOI：10.1002/adsc.201700969

  日期：2017.11.23

  concept for the synthesis of branched N‐acetyllactosamine (LacNAc) glycan structures. Through a combination of sequential enzymatic and chemical reactions of Leloir‐glycosyltransferases, galactose oxidase and reductive amination, we obtained branched glycan oligomers with a variation of LacNAc and/or N′,N′′‐diacetyllactosamine (LacdiNAc) glycan epitopes. Incorporation of a branching point was accomplished

  我们在这里提出了一个新的概念，用于合成支链N-乙酰基乳糖胺（LacNAc）聚糖结构。通过Leloir糖基转移酶，半乳糖氧化酶和还原胺化的顺序酶促和化学反应的组合，我们获得了具有LacNAc和/或N'，N''变异的支链聚糖低聚物-二乙酰基乳糖胺（LacdiNAc）聚糖表位。分支点的引入是通过优化的半乳糖氧化酶方案实现的，该方案可在LacNAc低聚物的末端半乳糖上呈现C-6醛官能团。通过糖基转移酶延长聚糖链后，将含C-6醛的线性结构单元与胺连接基官能化的聚糖偶联。发现甲醇和50°C的温度是α-甲基吡啶硼烷催化的还原胺化反应的最佳条件。在制备批次中，以高合成产率（约81％）获得了化学支链的聚糖。通过制备型HPLC分离产物，总收率良好（> 60％）。通过ESI-MS和NMR证明了结构的完整性。本文合成的分支LacNAc低聚物具有Lac（di）NAc表位的变异，并被证实是人Galectin-3（Ga