(2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranose
• 英文别名: 2-amino-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranose；GlcN(b1-4)GlcNAc(b1-4)GlcNAc(b1-4)b-GlcNAc；N-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₃₀H₅₂N₄O₂₀
• 分子量: 788.758
• InChiKey: PELBXIOURXZECK-WZWANHNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.3
• 重原子数：
  54
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  380
• 氢给体数：
  14
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  在 Aspergillus oryzae β-galactosidase 作用下， 以 水 为溶剂， 反应 20.0h， 生成 (2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-2-deoxy-α-D-glucopyranose 、 (2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  高效化学酶法合成脂壳寡糖植物生长促进剂

  摘要：

  这是已接受的手稿，已通过RSC出版同行评审过程，并已被接受出版。接受的手稿在接受后不久就会在线发布。一旦可用，此版本的文章将被完全编辑，格式化并提供高级阅读的高级文章代替。

  DOI：

  10.1039/c5gc00623f

文献信息

• From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG-chitotriomycin
  作者：Guillaume Despras、Aurélien Alix、Dominique Urban、Boris Vauzeilles、Jean-Marie Beau

  DOI：10.1002/anie.201406802

  日期：2014.10.27

  The direct and chemoselective N‐transacylation of peracetylated chitooligosaccharides (COSs), readily obtained from chitin, to give per‐N‐trifluoroacetyl derivatives offers an attractive route to size‐defined COSs and derived glycoconjugates. It involves the use of various acceptor building blocks and trifluoromethyl oxazoline dimer donors prepared with efficiency and highly reactive in 1,2‐trans glycosylation

  容易从几丁质中获得的过乙酰化壳寡糖（COSs）的直接和化学选择性N-酰基化，生成过N-三氟乙酰基衍生物，为规模确定的COS和衍生的糖缀合物提供了诱人的途径。它涉及使用各种受体构件和三氟甲基恶唑啉二聚体供体，这些供体在1,2-反式糖基化反应中高效且具有高反应性。该方法用于制备对植物具有高活性的重要共生糖脂，以及用于昆虫，真菌和细菌N-乙酰氨基葡萄糖苷酶的强效特异性抑制剂TMG-chichitriomycin 。
• Chitooligosaccharide Synthesis Using an Ionic Tag
  作者：Laura Gillard、Anh-Tuan Tran、François-Didier Boyer、Jean-Marie Beau

  DOI：10.1002/ejoc.201501476

  日期：2016.2

  An environmentally improved synthesis of the N-differentiated chitotetrasaccharide CO-IV-(NH2), a key intermediate for the preparation of lipochitooligosaccharides and the TMG-chitotriomycin, is reported based on a chromatography-free ionic-liquid tagging approach. The method involves the glycosylation of ionic-liquid-tagged acceptors with thioglucosamine donors leading to the stereoselective formation

  N-分化的壳四糖 CO-IV-(NH2) 是一种用于制备脂壳寡糖和 TMG-壳三霉素的关键中间体，基于无色谱离子液体标记方法进行了环境改进的合成。该方法涉及离子液体标记的受体与硫代葡糖胺供体的糖基化，导致 β-(14) 连接的含葡糖胺低聚物的立体选择性形成。
• [EN] MOLECULES WITH SOLUBILITY TAG AND RELATED METHODS<br/>[FR] MOLÉCULES AYANT UNE ÉTIQUETTE DE SOLUBILITÉ ET PROCÉDÉS ASSOCIÉS
  申请人：MERCK PATENT GMBH

  公开号：WO2022058548A1

  公开（公告）日：2022-03-24

  The present disclosure relates to molecules with a solubility tag, wherein the solubility tag comprises a chito-oligosaccharide, and to methods for increasing the solubility of a molecule. Moreover, the present disclosure relates to antibody-drug conjugates with solubility tag, methods and compounds for preparing such antibody-drug conjugates, methods for increasing the solubility of antibody-drug conjugates, antibody-drug conjugates prepared by such methods, as well as the use of such antibody-drug conjugates in medical treatment.

  本公开涉及带有溶解度标记的分子，其中溶解度标记包括壳寡糖，并且涉及增加分子溶解度的方法。此外，本公开涉及带有溶解度标记的抗体药物结合物，用于制备该抗体药物结合物的方法和化合物，增加抗体药物结合物溶解度的方法，通过这些方法制备的抗体药物结合物，以及在医疗治疗中使用这种抗体药物结合物。
• 10.1016/j.carres.2024.109144
  作者：He, Yuanchang、Zhang, Chenghui、Zhang, Xueying、Li, Yongcheng、Zhang, Qiao

  DOI：10.1016/j.carres.2024.109144

  日期：——

  Moreover, the amount of Chit2 adsorbed by chitin increased from 41.7 to 58.2 mg/g. Fourier transform infrared spectrometry revealed that PAW could break the β-1,4-glycosidic bonds of chitin (but had no effects on the hydrogen and amido bonds), thereby decreasing the molecular weight and crystallinity of the polysaccharide, which caused its structural damage and enhanced its enzymatic hydrolysis by chitinase

  甲壳低聚糖是甲壳素的水解产物，具有优于甲壳素本身的生物活性和应用价值；然而，甲壳素的有序和高度结晶结构使其难以被几丁质酶降解。在此，研究了等离子体活化水（PAW）预处理对甲壳素的理化性质、晶体结构和酶水解的影响。使用来自 (Chit2) 的几丁质酶水解经过 PAW 预处理的几丁质（PAW 活化时间为 5 分钟），与未经处理的几丁质相比，产生的还原糖增加了 71%，其中几丁质水解程度比未经预处理的几丁质增加了 13%。治疗后恢复至23%。此外，甲壳素吸附的Chit2量从41.7 mg/g增加到58.2 mg/g。傅里叶变换红外光谱分析表明，PAW可以打断甲壳素的β-1,4-糖苷键（但对氢键和酰胺键没有影响），从而降低多糖的分子量和结晶度，造成其结构破坏和通过几丁质酶增强其酶促水解。因此，PAW 预处理可以被认为是一种简单、有效且环保的甲壳素生物转化方法，因为其更容易水解产生高价值的产品。
• Efficient chemoenzymatic synthesis of lipo-chitin oligosaccharides as plant growth promoters
  作者：R. Chambon、G. Despras、A. Brossay、B. Vauzeilles、D. Urban、J.-M. Beau、S. Armand、S. Cottaz、S. Fort

  DOI：10.1039/c5gc00623f

  日期：——

  This is an Accepted Manuscript, which has been through the RSC Publishing peer review process and has been accepted for publication. Accepted manuscripts are published online shortly after acceptance. This version of the article will be replaced by the fully edited, formatted and proof read Advance Article as soon as this is available.

  这是已接受的手稿，已通过RSC出版同行评审过程，并已被接受出版。接受的手稿在接受后不久就会在线发布。一旦可用，此版本的文章将被完全编辑，格式化并提供高级阅读的高级文章代替。