3-[(N-Benzyloxycarbonyl)amino]propyl 2-N-acetamido-2-deoxy-β-D-glucopyranoside | 87906-03-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(N-Benzyloxycarbonyl)amino]propyl 2-N-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: 3-(benzyloxycarbonylamino)propyl 2-acetamido-2-deoxy-β-D-glucopyranoside；benzyl N-[3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl]carbamate
• CAS: 87906-03-4
• 化学式: C₁₉H₂₈N₂O₈
• 分子量: 412.44
• InChiKey: KKNLSAQCEDUBRW-DUQPFJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  147
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-[(N-Benzyloxycarbonyl)amino]propyl 2-N-acetamido-2-deoxy-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 水 、 异丙醇 为溶剂， 反应 2.0h， 以78%的产率得到3-aminopropyl 2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  N-乙酰氨基葡糖衍生物的化学合成及其作为中生根瘤菌甲壳质寡糖合酶NodC的糖基受体的用途

  摘要：

  摘要根瘤菌细菌合成了脂-几丁质寡糖信号分子（Nod因子），这对于在宿主植物根部形成共生器官至关重要，这一过程称为结瘤。Nod因子中的几丁质寡糖部分的生物合成是通过根瘤菌N-乙酰氨基葡萄糖氨基转移酶NodC进行的。用于体内几丁质寡糖合成的初始受体或引物是未知的。为了研究NodC的受体特异性，我们合成了具有不同糖苷配基的N-乙酰氨基葡糖（GlcNAc）衍生物，并使用表达lotorhizobium loti几丁质寡糖合酶NodC的大肠杆菌菌株的膜制剂在体外测试了它们是否为NodC的受体。使用薄层色谱法分析反应产物表明，含有简单烷基链或连接C-1的其他疏水基团的GlcNAc衍生物是NodC的受体。该酶似乎对糖苷配基是β-连接的受体具有特异性。NodC仍将其中GlcNAc的N-乙酰基部分的甲基被烯丙氧基或苄氧基取代的GlcNAc衍生物用作受体。因此，在该位置上的原始甲基对于NodC和GlcNAc之间

  DOI：

  10.1016/s0008-6215(99)00190-1
• 作为产物：
  描述：

  3-(苄氧羰基氨基)-1-丙醇 在 potassium tert-butylate 、 四氯化锡 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 22.0h， 生成 3-[(N-Benzyloxycarbonyl)amino]propyl 2-N-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  N-乙酰氨基葡糖衍生物的化学合成及其作为中生根瘤菌甲壳质寡糖合酶NodC的糖基受体的用途

  摘要：

  摘要根瘤菌细菌合成了脂-几丁质寡糖信号分子（Nod因子），这对于在宿主植物根部形成共生器官至关重要，这一过程称为结瘤。Nod因子中的几丁质寡糖部分的生物合成是通过根瘤菌N-乙酰氨基葡萄糖氨基转移酶NodC进行的。用于体内几丁质寡糖合成的初始受体或引物是未知的。为了研究NodC的受体特异性，我们合成了具有不同糖苷配基的N-乙酰氨基葡糖（GlcNAc）衍生物，并使用表达lotorhizobium loti几丁质寡糖合酶NodC的大肠杆菌菌株的膜制剂在体外测试了它们是否为NodC的受体。使用薄层色谱法分析反应产物表明，含有简单烷基链或连接C-1的其他疏水基团的GlcNAc衍生物是NodC的受体。该酶似乎对糖苷配基是β-连接的受体具有特异性。NodC仍将其中GlcNAc的N-乙酰基部分的甲基被烯丙氧基或苄氧基取代的GlcNAc衍生物用作受体。因此，在该位置上的原始甲基对于NodC和GlcNAc之间

  DOI：

  10.1016/s0008-6215(99)00190-1

文献信息

• Chemo-enzymatic synthesis of glycopolymers and sequential glycopeptides bearing lactosamine and sialyl Lewisx unit pendant chains
  作者：Florence Sallas、Shin-Ichiro Nishimura

  DOI：10.1039/b001612h

  日期：——

  A variety of glycoconjugates bearing either N-acetyllactosamine or sialyl Lewisx units have been synthesised in a chemo-enzymatic way. This includes the synthesis of glycopolymer copolymerised with acrylamide and whose glucosamine unit was substituted with different kinds of side-chain. Glycopeptides with different spacer-arm glucosamine units have also been prepared and polymerised. The sugar chain

  已经以化学酶促的方式合成了各种带有N-乙酰基乳糖胺或唾液酸化的Lewis x单元的糖缀合物。这包括与丙烯酰胺共聚的糖聚合物的合成，其糖胺单元被不同种类的侧链取代。还已经制备并聚合了具有不同间隔臂葡糖胺单元的糖肽。然后使用糖基转移酶拉长糖链，以提供新的连续糖肽。在这些情况下，聚合糖簇效应导致高效的酶促糖基化。然而，根据用于每种底物的反应条件，已经注意到一些差异。
• In vivo Neutralization of Naturally Existing Antibodies against Linear ?(1,3)-Galactosidic Carbohydrate Epitopes by Multivalent Antigen Presentation: A Solution for the First Hurdle of Pig-to-Human Xenotransplantation
  作者：Rudolf O. Duthaler、Beat Ernst、Reto Fischer、Andreas G. Katopodis、Willy Kinzy、Wolfgang Marterer、Reinhold Oehrlein、Markus B. Streiff、Gebhard Thoma

  DOI：10.2533/chimia.2010.23

  日期：——

  Pig-to-human xenotransplantation of islet cells or of vascularized organs would offer a welcome treatment alternative for the ever-increasing number of patients with end-stage organ failure who are waiting for a suitable allograph. The main hurdle are preexisting antibodies, most of which are specific for 'Linear-B', carbohydrate epitopes terminated by the unbranched Gal-?(1,3)Gal disaccharide. These antibodies are responsible for the 'hyper-acute rejection' of the xenograft by complement mediated hemorrhage. For depletion of such antibodies we have developed an artificial injectable antigen, a glycopolymer (GAS914) with a charge neutral poly-lysine backbone (degree of polymerization n = 1000) and 25% of its side chains coupled to Linear-B-trisaccharide. With an average molecular weight of 400 to 500 kD, presenting 250 trisaccharide epitopes per molecule, this multivalent array binds anti-?Gal antibodies with at least three orders of magnitude higher avidity on a per-saccharide basis than the monomeric epitope. In vivo experiments with non-human primates documented that rather low doses – 1 to 5 mg/kg of GAS914 injected i.v. – efficiently reduce the load of anti-Linear-B antibodies quickly by at least 80%. This treatment can be repeated without any sensitization to GAS914. Interestingly, although the antibody levels start raising 12 h after injection, they do not reach pretreatment levels. The polymer is degraded and excreted within hours, with a minute fraction remaining in lymphoid tissue of anti-?Gal producing animals only, probably binding to and inhibiting antibody-producing B-cells. The results of pig-to-non-human primate xenotransplantations established GAS914 as a relevant therapeutic option for pig-to-human transplantations as well. The synthesis of GAS914 was successfully scaled up to kg amounts needed for first clinical studies. Key was the use of galactosyl transferases and UDP-galactose for the synthesis of the trisaccharide.

  将猪到人体异种移植的胰岛细胞或血管化器官可为等待合适同种移植物的晚期器官功能衰竭患者提供一种受欢迎的治疗选择。主要障碍是已存在的抗体，其中大多数特异性针对以线性-B结尾的半乳糖-半乳糖二糖为终点的碳水化合物表位。这些抗体负责通过补体介导的出血引起的异种移植物的“超急性排斥”。为了清除这些抗体，我们开发了一种人工可注射抗原，一种具有电荷中性的聚赖氨酸骨架（聚合度n = 1000）和其25%的侧链偶联到线性-B三糖的糖聚合物（GAS914）。平均分子量为400至500千道因，每个分子呈现250个三糖表位，这种多价阵列以每糖基的至少三个数量级更高的亲和力结合抗-半乳糖抗体，而不是单体表位。非人灵长类动物的体内实验表明，注射i.v.的GAS914低剂量（1至5毫克/千克）能够迅速将至少80%的抗线性-B抗体负荷有效降低。这种治疗可以反复进行而不会对GAS914产生任何敏感性。有趣的是，尽管抗体水平在注射后12小时开始上升，但并未达到治疗前水平。聚合物在几小时内降解并排出体外，只有极小部分残留在仅产生抗-半乳糖的动物的淋巴组织中，可能与并抑制产生抗体的B细胞结合。猪到非人灵长类动物的异种移植结果将GAS914确立为猪到人体移植的相关治疗选择。GAS914的合成已成功扩大到首次临床研究所需的公斤级数量。关键是使用半乳糖转移酶和UDP-半乳糖合成三糖。
• Rational Design, Synthesis, and Characterization of Novel Inhibitors for Human β1,4-Galactosyltransferase
  作者：Kenji Takaya、Noriko Nagahori、Masaki Kurogochi、Tetsuya Furuike、Nobuaki Miura、Kenji Monde、Yuan Chuan Lee、Shin-Ichiro Nishimura

  DOI：10.1021/jm0504297

  日期：2005.9.1

  An affinity labeling reagent, uridine 5'-(6-amino-2-[(7-bromomethyl-2-naphthyl)methoxy-carbonylmethoxy]ethoxy}acetyl-6-deoxy-alpha-D-galactopyranosyl) diphosphate (1a), was designed on the basis of 3D docking simulation and synthesized to investigate the functional role of Trp310 residue located in the small loop near the active site of human recombinant galactosyltransferase (beta GalT-1). Mass spectrometric analysis revealed that the Trp310 residue of beta GalT1 can be selectively modified with the naphthylmethyl group of compound la at the C-3 position of the indole ring. This result motivated us to synthesize novel uridine-5'-diphosphogalactose (UDP-Gal) analogues as candidates for mechanism-based inhibitors for beta GalT-1. We found that uridine 5'-(6-O-[10-(2-naphthyl)-3,6,9-trioxadecanyl]-alpha-D-galactopyranosyl) diphosphate (2) is the strongest inhibitor (K-i = 1.86 mu M) against UDP-Gal (K-m = 4.91 mu M) among compounds reported previously. A cold spray ionization time-of-flight mass spectrometry study demonstrated that the complex of this inhibitor and beta GalT-1 cannot interact with an acceptor substrate in the presence of Mn2+.
• Synthetic Potential of Fucosyltransferase III for the Synthesis of Fluorescent‐labeled Milk Oligosaccharides
  作者：Said Rabbani、Federica Compostella、Laura Franchini、Beatrice Wagner、Luigi Panza、Beat Ernst

  DOI：10.1080/07328300500341965

  日期：2005.11.1

  Various fundamental biologic roles of milk oligosaccharides have been recognized; however, their structure-affinity relationship is still not fully revealed. Herein, we describe the synthesis of the fluorescent-labeled milk oligosaccharides 3-(5-dimethylaminonaphthalene-1-sulfonylamino)propyl beta-D-galactopyranosyl-(1 -> 3)-[alpha-L-fucopyranosyl-(1 -> 4)]-2-acetamido-2-deoxy-beta-D-glucopyranoside (1) and 3-(5-dimethylamino-naphthalene-1-sulfonylamino)propyl beta-D-galactopyranosyl-(1 -> 3)-[alpha-L-fucopyranosyl-(1 -> 4)]-beta-D-glucopyranoside (2) as useful tools for synthetic, analytic, and biologic applications. For the fucosylation of lactose and lacto- N -biose, the chemical and the enzymatic syntheses using fucosyltransferase III were compared.
• Artificial Golgi Apparatus: Globular Protein-like Dendrimer Facilitates Fully Automated Enzymatic Glycan Synthesis
  作者：Takahiko Matsushita、Izuru Nagashima、Masataka Fumoto、Takashi Ohta、Kuriko Yamada、Hiroki Shimizu、Hiroshi Hinou、Kentaro Naruchi、Takaomi Ito、Hirosato Kondo、Shin-Ichiro Nishimura

  DOI：10.1021/ja106955j

  日期：2010.11.24

  Despite the growing importance of synthetic glycans as tools for biological studies and drug discovery, a lack of common methods for the routine synthesis remains a major obstacle. We have developed a new method for automated glycan synthesis that employs the enzymatic approach and a dendrimer as an ideal support within the chemical process. Recovery tests using a hollow fiber ultrafiltration module have revealed that monodisperse G6 (MW = 58 kDa) and G7 (MW = 116 kDa) poly(amidoamine) dendrimers exhibit a similar profile to BSA (MW = 66 kDa). Characteristics of the globular protein-like G7 dendrimer with high solubility and low viscosity in water greatly enhanced throughput and efficiency in automated synthesis while random polyacrylamide-based supports entail significant loss during the repetitive reaction/separation step. The present protocol allowed for the fully automated enzymatic synthesis of sialyl Lewis X tetrasaccharide derivatives over a period of 4 days in 16% overall yield from a simple N-acetyl-D-glucosamine linked to an aminooxy-functionalized G7 dendrimer.