chitobiose octaacetate | 117467-63-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: chitobiose octaacetate
• 英文别名: octaacetylchitobiose；Chitobiose-octaacetat；GlcNAc3Ac4Ac6Ac(b1-4)b-GlcNAc1Ac3Ac6Ac；[(2R,3S,4R,5R,6S)-5-acetamido-3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-4,6-diacetyloxyoxan-2-yl]methyl acetate
• CAS: 117467-63-7
• 化学式: C₂₈H₄₀N₂O₁₇
• 分子量: 676.629
• InChiKey: JUYKRZRMNHWQCD-LMWPHQNTSA-N

物化性质

• 沸点：
  805.3±65.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  47
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  244
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  chitobiose octaacetate 在 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 N,N'-diacetylchitobiose
  参考文献：
  名称：

  Fully Synthetic Granulocyte Colony-Stimulating Factor Enabled by Isonitrile-Mediated Coupling of Large, Side-Chain-Unprotected Peptides

  摘要：

  Human granulocyte colony-stimulating factor (G-CSF) is an endogenous glycoprotein involved in hematopoiesis. Natively glycosylated and nonglycosylated recombinant forms, lenograstim and filgrastim, respectively, are used clinically to manage neutropenia in patients undergoing chemotherapeutic treatment. Despite their comparable therapeutic potential, the purpose of O-linked glycosylation at Thr133 remains a subject of controversy. In light of this, we have developed a synthetic platform to prepare G-CSF aglycone with the goal of enabling access to native and designed glycoforms with site-selectivity and glycan homogeneity. To address the synthesis of a relatively large, aggregation-prone sequence, we advanced an isonitrile-mediated ligation method. The chemoselective activation and coupling of C-terminal peptidyl Gly thio acids with the N-terminus of an unprotected peptide provide ligated peptides directly in a manner complementary to that with conventional native chemical ligation-desulfurization strategies. Herein, we describe the details and application of this method as it enabled the convergent total synthesis of G-CSF aglycone.

  DOI：

  10.1021/jacs.5b08754
• 作为产物：
  描述：

  2-amino-2-deoxy-β-D-glucopyranosyl-(1->4)-2-amino-2-deoxy-D-glucopyranose 生成 chitobiose octaacetate
  参考文献：
  名称：

  NAGJO, FUMIO;SAKAI, KAZUO;USUI, TAICHI;TAKAI, IZUMI;ISHIDO, YOSHIHARU, J. CARBOHYDR. CHEM., 7,(1988) N 1, 67-82

  摘要：

  DOI：

文献信息

• Chitinase Inhibition by Chitobiose and Chitotriose Thiazolines
  作者：James M. Macdonald、Chris A. Tarling、Edward J. Taylor、Rebecca J. Dennis、David S. Myers、Spencer Knapp、Gideon J. Davies、Stephen G. Withers

  DOI：10.1002/anie.200906644

  日期：2010.3.29

  hydrolysis of chitin were found to be potent inhibitors of chitinase A. The high affinity and enzymatic stability of a readily synthesized thioamide trisaccharide (two molecules of which are shown in the enzyme active site), and the mechanism‐based mode of inhibition, make this analogue a promising candidate for broad‐spectrum chitinase inhibition.

  良好的模仿方法：发现几丁质酶水解过程中形成的恶唑啉中间体的二糖和三糖类似物是几丁质酶A的有效抑制剂。易于合成的硫代酰胺三糖具有很高的亲和力和酶促稳定性（在图2中显示了两个分子）。酶活性位点），以及基于机理的抑制方式，使得该类似物成为广谱几丁质酶抑制的有希望的候选者。
• Syntheses of model oligosaccharides of biological significance. XI. A short synthesis of fucosylated chitobiosides, also bound to asparagine in a synthon (as in <i>N</i>-linked glycoproteins)
  作者：Ho Huat Lee、Jose A. B. Baptista、Jiri J. Krepinsky

  DOI：10.1139/v90-148

  日期：1990.6.1

  the preparation of the trisaccharide GlcNAc(β1-4)-[Fuc(α 1-6)-]GlcNAc(β 1-) (1) and of the protected form of GlcNAc(β 1-4)-[Fuc(α 1-6)-]GlcNAc(β1-Asn) (2). The key intermediate is benzyl 4,6-benzylidene chitobioside 5 giving the desired trisaccharide by insitu anomerization–glycosylation reaction with 2,3,4-tribenzylfucosyl bromide. The benzyl glycoside in the trisaccharide 6 has been replaced by acetate

  我们描述了一种简单有效的制备三糖 GlcNAc(β1-4)-[Fuc(α 1-6)-]GlcNAc(β 1-) (1) 和保护形式的 GlcNAc(β 1- 4)-[Fuc(α 1-6)-]GlcNAc(β1-Asn) (2)。关键中间体是苄基 4,6-亚苄基壳二糖苷 5，通过与 2,3,4-三苄基岩藻糖基溴的原位异构化-糖基化反应得到所需的三糖。三糖6中的苄基糖苷已被乙酸酯和溴取代；该糖基化剂用于在一系列反应中制备甲基和 8-甲氧基羰基辛基糖苷以及异硫氰酸酯 12。后一化合物在与 1-苄基 N-苄氧羰基-L-天冬氨酸反应后得到化合物 13（2 的受保护衍生物），其应作为合成糖肽的合成子。关键词：糖肽，合成；寡糖，合成; 壳双糖苷；岩藻糖化壳二糖苷；N-连接的寡糖。
• Methods for detecting endoglycosidase activity
  申请人：Academisch Ziekenhuis bij de Universiteit van Amsterdam

  公开号：EP1359227A1

  公开（公告）日：2003-11-05

  The invention relates to detection of endoglycosidase activity and diagnostics of infertility and diseases wherein an altered amount of an endoglycosidase is involved. Two methods for detecting the endoglycosidase activity are disclosed that solve the problem of interference of the additional transglycosidase activity of endoglycosidases in an assay for endoglycosidase activity at high substrate concentrations. The first method involves substrates that cannot be glycosylated due to the absence of a hydroxyl group at the 4 position of the reducing end sugar substrate. The second method involves a further other molecule capable of being glycosylated for competition with the transglycosylation of the substrate. Methods of the synthesis of glycosylated substrates using the transglycosidase activity of endoglycosidases are also claimed.

  本发明涉及内糖苷酶活性的检测以及不孕症和涉及内糖苷酶量改变的疾病的诊断。 本发明公开了两种检测内切糖苷酶活性的方法，解决了内切糖苷酶的额外转糖苷酶活性对高浓度底物内切糖苷酶活性检测的干扰问题。 第一种方法涉及的底物由于还原性末端糖底物的 4 位没有羟基而不能被糖基化。 第二种方法涉及另一种能够被糖基化的分子，以与底物的转糖基化竞争。 此外，还提出了利用内切糖苷酶的转糖苷酶活性合成糖基化底物的方法。
• Means and methods for detecting endoglycosidase activity
  申请人：Aerts Gerardus Johannes Maria Franciscus

  公开号：US20050158814A1

  公开（公告）日：2005-07-21

  The invention discloses a method for detecting an activity of an endoglycosidase. The method includes providing the endoglycosidase with a substrate of the endoglycosidase and detecting cleavage of the substrate. The method further includes at least partly inhibiting the transglycosidase activity of the endoglycosidase. The transglycosidase activity may be inhibited by chemically modifying the substrate such that transglycosylation of the substrate by the endoglycosidase is at least partly inhibited while the endoglycosidase is still capable of cleaving the substrate. In one embodiment, the substrate comprises an oligosaccharide chain. Compounds and kits suitable for use in a method of the invention are also disclosed. Methods involving competitive inhibitors are also disclosed as are methods for the synthesis of glycosylated substrates involving the transglycosidase activity of an endoglycosidase.

  本发明公开了一种检测内糖苷酶活性的方法。该方法包括向内切糖苷酶提供内切糖苷酶的底物，并检测底物的裂解情况。该方法还包括至少部分抑制内糖苷酶的转糖苷酶活性。可通过化学修饰底物来抑制转糖苷酶活性，从而至少部分抑制内切糖苷酶对底物的转糖基化，同时内切糖苷酶仍能裂解底物。在一个实施方案中，底物包括寡糖链。本发明还公开了适用于本发明方法的化合物和试剂盒。还公开了涉及竞争性抑制剂的方法，以及涉及内切糖苷酶的转糖苷酶活性的糖基化底物合成方法。
• Improving Glycopeptide Synthesis:  A Convenient Protocol for the Preparation of β-Glycosylamines and the Synthesis of Glycopeptides
  作者：Christian P. R. Hackenberger、Mary K. O'Reill、Barbara Imperiali

  DOI：10.1021/jo047801v

  日期：2005.4.1

  Herein we apply a recently introduced protocol using ammonium carbamate in methanol to the amination of crude chitobiose leading to 1,beta-aminochitobiose. This simple, one-step procedure allows a facile preparation of unstable glycosylamines in contrast to the commonly implemented ammonium bicarbonate based amination of water-soluble carbohydrates. The new amination protocol leads to an improved synthesis of the key chitobiosyl-asparagine building block for the SPPS of glycopeptides. The utility of the method is demonstrated with the synthesis of a 39-amino acid glycoprotein.