(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-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-D-glucopyranose
• 英文别名: GlcN(b1-4)GlcNAc(b1-4)GlcNAc(b1-4)GlcNAc；N-[(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-SWVATGCDSA-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

• 作为反应物：
  描述：

  methyl 3-(undecyloxy)benzoate 、 (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-D-glucopyranose 在 Dowex 1x2-100 resin (HCO₃-) 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以22%的产率得到2-acetatamido-4-O-(2-acetamido-4-O-(2-acetamido-2-deoxy-4-O-(2-deoxy-2-(N-3-(undec-4Z-enyloxy)benzoyl)amino-β-D-glucopyranosyl)-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  WO2008/71672

  摘要：

  公开号：
• 作为产物：
  描述：

  N,N',N'',N'''-tetraacetylchitotetraose 在 Sinorhizobium meliloti NodB chitinoligosaccharide N-deacetylase 作用下， 以 aq. buffer 为溶剂， 以84 %的产率得到(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-D-glucopyranose
  参考文献：
  名称：

  Transport of N-acetylchitooligosaccharides and fluorescent N-acetylchitooligosaccharide analogs into rat liver lysosomes

  摘要：

  Free polymannose-type oligosaccharides (fOS) are processed by cytosolic enzymes to generate Man5GlcNAc which is transferred to lysosomes and degraded. Lysosomal fOS import was demonstrated in vitro but is poorly characterized in part due to lack of convenient substrates. As chitooligosaccharides (COS, oligomers β1,4-linked GlcNAc) block [3H]Man5GlcNAc transport into lysosomes, we asked if COS are themselves transported and if so, can they be chemically modified to generate fluorescent substrates.

  We show that COS are degraded by lysosomal hydrolases to generate GlcNAc, and robust ATP-dependent transport of [3H]COS2/4 di and tetrasaccharides into intact rat liver lysosomes was observed only after blocking lysosomal [3H]GlcNAc efflux with cytochalasin B. As oligosaccharides with unmodified reducing termini are the most efficient inhibitors of [3H]COS2/4 and [3H]Man5GlcNAc transport, the non-reducing GlcNAc residue of COS2-4 was de-N-acetylated using Sinorhizobium meliloti NodB, and the resulting amine substituted with rhodamine B (RB) to yield RB-COS2-4. The fluorescent compounds inhibit [3H]Man5GlcNAc transport and display temperature-sensitive, ATP-dependent transport into a sedimentable compartment that is ruptured with the lysosomotropic agent L-methyl methionine ester. Once in this compartment, RB-COS3 is converted to RB-COS2 further identifying it as the lysosomal compartment. RB-COS2/3 and [3H]Man5GlcNAc transports are blocked similarly by competing sugars, and are partially inhibited by the vacuolar ATPase inhibitor bafilomycin and high concentrations of the P-type ATPase inhibitor orthovanadate.

  These data show that Man5GlcNAc, COS2/4 and RB-COS2/3 are transported into lysosomes by the same or closely related mechanism and demonstrate the utility of COS modified at their non-reducing terminus to study lysosomal oligosaccharide transport.

  DOI：

  10.1093/glycob/cwad099

文献信息

• 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。
• 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 。
• [EN] SYNTHETIC COMPOUNDS USEFUL AS NODULATION AGENTS OF LEGUMINOUS PLANTS AND PREPARATION PROCESSES THEREOF<br/>[FR] COMPOSES SYNTHETIQUES UTILES COMME AGENTS DE NODULATION DES LEGUMINEUSES ET PROCEDES DE PREPARATION DE CES COMPOSES
  申请人：BAYER CROPSCIENCE SA

  公开号：WO2005063784A1

  公开（公告）日：2005-07-14

  The present invention relates to synthetic compounds that are active on plants, especially as legume nodulation factors, and also as plant growth stimulators, and to methods for preparing such compounds, which are of formula (I):'Veuillez insérer la formule chimique de la version papier' (I)

  这项发明涉及对植物具有活性的合成化合物，特别是作为豆科植物结瘤因子，以及作为植物生长促进剂，并涉及制备这种化合物的方法，其化学式为(I)。
• New access to lipo-chitooligosaccharide nodulation factors
  作者：Martin Ohsten Rasmussen、Bridget Hogg、Jean-Jacques Bono、Eric Samain、Hugues Driguez

  DOI：10.1039/b403575e

  日期：——

  Sulfonated and non-sulfonated lipo-chitooligosaccharides involved in Sinorhizobium meliloti–legume symbiosis are efficiently obtained on a multi mg scale by a 2-step procedure combining biotechnological and chemical approaches.

  通过生物技术和化学方法相结合的两步程序，在多毫克规模上高效地获得了参与黑麦-豆科植物共生的磺化和非磺化壳寡糖。
• [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。