GDP-Fuc

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: GDP-Fuc
• 英文别名: GDP-fucose；guanosine 5’-diphospho-L-fucose；[[(2R,3S,4R,5R)-5-(2-amino-6-hydroxypurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl] hydrogen phosphate
• 化学式: C₁₆H₂₅N₅O₁₅P₂
• 分子量: 589.347
• InChiKey: LQEBEXMHBLQMDB-QIXZNPMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.7
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  307
• 氢给体数：
  9
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  GDP-Fuc 在 palladium dihydroxide FucT-III 、 Ni⁽²⁺⁾-Agarose 、 水 、 氢气 、 sodium cacodylate 、 manganese(ll) chloride 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 生成 2,2-bis-[O-β-D-galactopyranosyl-(1->4)-(2-acetamido-2-deoxy-3-O-α-L-fucopyranosyl-β-D-glucopyranosyloxy)]-propane-1,3-diol
  参考文献：
  名称：

  Chemo-enzymatic synthesis of a divalent sialyl Lewisx ligand with restricted flexibility

  摘要：

  To study the influence of the entropic factor in cluster cooperative effects, a divalent sialyl Lewis(x) ligand with restricted flexilbility was chemo-enzymatically synthesized. First, a cyclized precursor with both glucosamine residues bridged together by a succinyl group was readily obtained in 42% yield by treatment of 2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-beta-D-glucopyranosyloxy)-propane with succinyl chloride. After deacetylation, this precursor was subjected to stepwise enzymatic elongation utilizing successively, soluble galactosyltransferase, then recombinant sialyltransferase and fucosyltransferase; the latter enzymes immobilized on Ni2+-Agarose, to afford, after debenzylation, a divalent sialyl Lewis(+) ligand of restricted flexibility. in 45% overall yield. Following the same enzymatic sequence, a totally flexible ligand, required as a reference compound for evaluation of inhibitory activity toward selectins, was also prepared from 2,2(bis-benzyloxymethyl)-1,3-bis(2-acetamido-2-deoxy-beta-D-glucopyranosyloxy)-propane, as well as both related divalent Lewis' molecules lacking the sialic acids, the rigid one and the flexible one. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00129-0
• 作为产物：
  描述：

  (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 在 palladium dihydroxide 草酰溴 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 GDP-Fuc
  参考文献：
  名称：

  Rapid Chemical Synthesis of Sugar Nucleotides in a Form Suitable for Enzymic Oligosaccharide Synthesis

  摘要：

  DOI：

  10.1021/jo00106a007

文献信息

• Cation exchange assisted binding-elution strategy for enzymatic synthesis of human milk oligosaccharides (HMOs)
  作者：Hailiang Zhu、Zhigang Wu、Madhusudhan Reddy Gadi、Shuaishuai Wang、Yuxi Guo、Garrett Edmunds、Wanyi Guan、Junqiang Fang

  DOI：10.1016/j.bmcl.2017.08.041

  日期：2017.9

  A cation exchange assisted binding-elution (BE) strategy for enzymatic synthesis of human milk oligosaccharides (HMOs) was developed. An amino linker was used to provide the cation ion under acidic condition which can be readily bound to cation exchange resin and then eluted off by saturated ammonium bicarbonate. Ammonium bicarbonate in the collections was easily removed by vacuum evaporation. This

  开发了用于人乳寡糖（HMO）酶促合成的阳离子交换辅助结合-洗脱（BE）策略。使用氨基接头在酸性条件下提供阳离子，该阳离子可以很容易地与阳离子交换树脂结合，然后用饱和碳酸氢铵洗脱。收集物中的碳酸氢铵很容易通过真空蒸发除去。该策略避免了糖基转移酶与固体支持物或大型聚合物之间的不相容问题，并且中间产物无需纯化。用目前的方法，HMOs和岩藻糖基化的HMOs的polyLacNAc主链可以顺利合成。
• Use of the “core-2”-N-acetylglucosaminyltransferase in the chemical-enzymatic synthesis of a sialyl-Lex-containing hexasaccharide found on O-linked glycoproteins
  作者：Reinhold Oehrlein、Ole Hindsgaul、Monica M. Palcic

  DOI：10.1016/0008-6215(93)80011-3

  日期：1993.5

  obtained in a single step of affinity chromatography is suitable for use in preparative oligosaccharide synthesis. In conjunction with previously described preparations of beta-(1-->4)-galactosyltransferase (EC 2.4.1.22), alpha-(2-->3)-sialytransferase (EC 2.4.99.6) and alpha-(1-->3/4)-fucosyltransferase (EC 2.4.1.65), the GlcNAcT was used in the first step of a sequence which converted the disaccharide

  简单制备“核心II” N-乙酰氨基葡萄糖氨基转移酶（UDP-D-GlcpNAc：beta-D-Galp-（1-> 3）-alpha-D-GalpNAc（从GlcNAc到GalNAc）beta-（1-报道了来自商业小鼠肾丙酮粉的> 6）-GlcNAc-转移酶，GlcNAcT，EC 2.4.1.102）。在亲和层析的单个步骤中获得的酶适用于制备寡糖的合成。与先前描述的β-（1-> 4）-半乳糖基转移酶（EC 2.4.1.22），α-（2-> 3）-唾液酸转移酶（EC 2.4.99.6）和α-（1-> 3/4）-岩藻糖基转移酶（EC 2.4.1.65），GlcNAcT用于将双糖β-D-Galp-（1-> 3）-alpha-D-GalpNAc-OR转化为含唾液酸基LeX的结构alpha-D-NeupAc-（2-> 3）-beta-D-Galp-（1-> 4）-[alpha-L-Fucp-（1--
• Chemoenzymatic Synthesis of N-glycan Positional Isomers and Evidence for Branch Selective Binding by Monoclonal Antibodies and Human C-type Lectin Receptors
  作者：Begoña Echeverria、Sonia Serna、Silvia Achilli、Corinne Vivès、Julie Pham、Michel Thépaut、Cornelis H. Hokke、Franck Fieschi、Niels-Christian Reichardt

  DOI：10.1021/acschembio.8b00431

  日期：2018.8.17

  Here, we describe a strategy for the rapid preparation of pure positional isomers of complex N-glycans to complement an existing array comprising a larger number of N-glycans and smaller glycan structures. The expanded array was then employed to study context-dependent binding of structural glycan fragments by monoclonal antibodies and C-type lectins. A partial enzymatic elongation of semiprotected

  在这里，我们描述了一种快速制备复杂N-聚糖的纯位置异构体的策略，以补充包含大量N-聚糖和较小聚糖结构的现有阵列。然后将扩展的阵列用于研究单克隆抗体和C型凝集素对结构聚糖片段的背景依赖性结合。通过制备型HPLC将半保护核心结构的部分酶促延伸与位置异构体的保护基辅助分离相结合。该方法避免了繁琐的触角化学区分，被用于制备八种带有Galβ1,4GlcNAc（LN），GalNAcβ1,4GlcNAc（LDN）和GalNAcβ1,4[Fucα1,3] GlcNAc（LDNF）的双触角N-聚糖。 ）出现在一个或两个触角上的图案。三种抗Le抗体结合特异性的筛选针对曼氏沙门氏菌聚糖和先天免疫系统的三个C型凝集素受体（即DC-SIGN，DC-SIGNR和LSECtin）产生的X单克隆IgM抗体显示出令人惊讶的上下文相关的精细特异性，可识别聚糖基序。此外，我们观察到，通过测试的C型凝集素，一个单独的位置异构体比
• Enzymatic Synthesis of Human Milk Fucosides α1,2-Fucosyl<i>para</i>-Lacto-<i>N</i>-Hexaose and its Isomeric Derivatives
  作者：Jia-Lin Fang、Teng-Wei Tsai、Chin-Yu Liang、Jyun-Yi Li、Ching-Ching Yu

  DOI：10.1002/adsc.201800518

  日期：2018.9.3

  production of extended type‐1 and type‐2 N‐acetyllactosamine (LacNAc) backbones and hybrid chains. Further fucosylation efficiency of two α1,2‐fucosyltransferases on both type‐1 and type‐2 chains of the hexasaccharide was investigated to achieve practical synthesis of the fucosylated glycans. The availability of structurally defined HMOs offers a practical approach for investigating future biological applications

  的酶促合成段-lacto- Ñ -hexaose及其异构结构以及那些α1,2岩藻糖化的变体在人乳寡糖（HMO的）天然存在的使用顺序一锅酶体系达到了。已开发出包括细菌糖基转移酶和相应的糖核苷酸生成酶的三种糖基化途径，以促进高效生产扩展的1型和2型 氮-乙酰基乳糖胺（LacNAc）骨架和杂合链。研究了两个α1,2-岩藻糖基转移酶在六糖的1型和2型链上的进一步岩藻糖基化效率，以实现岩藻糖基化聚糖的实际合成。结构明确的HMO的可用性为研究未来的生物应用提供了一种实用的方法。
• Ionic-liquid-based MS probes for the chemo-enzymatic synthesis of oligosaccharides
  作者：M. Carmen Galan、Anh Tuan Tran、Karen Bromfield、Said Rabbani、Beat Ernst

  DOI：10.1039/c2ob25855b

  日期：——

  A new N-benzenesulfonyl-based ionic-liquid mass spectroscopy label (I-Tag2) for covalent attachment to substrates has been prepared. I-Tag2 was used to monitor oligosaccharide elongation and serve as a purification handle. Starting from chemically synthesized I-Tag2-labelled N-acetyl glucosamine (GlcNAc) 1, I-Tag2-LacNAc (Galβ(1–4)GlcNAc) 2 and I-Tag2-LewisX (Galβ(1–4)[Fucα(1–3)]GlcNAc) 3, which are oligosaccharides of biological relevance, were enzymatically prepared. The apparent kinetic parameters for the enzyme catalysed transformations with β-1,4-galactosyltransferase (β-1,4-GalT) and fucosyltransferase VI (FucT VI) were measured by LC-MS demonstrating the applicability and versatility of the new I-Tags in enzymatic transformations with glycosyltransferases.

  一种新的N-苯磺酰基离子液体质谱标签（I-Tag2）已被制备，用于与基材的共价结合。I-Tag2被用来监测寡糖的延伸，并作为纯化工具。从化学合成的I-Tag2标记的N-乙酰氨基葡萄糖（GlcNAc）1出发，酶促合成了具有生物相关性的N-标记的乳糖（LacNAc，Galβ(1–4)GlcNAc）2和LewisX（Galβ(1–4)[Fucα(1–3)]GlcNAc）3。通过液相色谱-质谱（LC-MS）测量了与β-1,4-半乳糖基转移酶（β-1,4-GalT）和L-富糖转移酶VI（FucT VI）催化转化的明显动力学参数，证实了新I-Tag在糖苷转移酶酶促转化中的适用性和多功能性。