β-D-galactopyranosyl-(1->4)-O-2-acetamido-2-deoxy-β-D-glucopyranose | 47491-70-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-galactopyranosyl-(1->4)-O-2-acetamido-2-deoxy-β-D-glucopyranose
• 英文别名: β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranose；2-Acetamido-4-O-(β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranose；β-D-galactopyranosyl-(1-4)-2-acetamido-2-deoxy-β-D-glucose；βDGal(1-4)βDGlcNAc；N-acetyl-β-lactosamine；Galβ1-4GlcNAc；N-acetyllactosamine；N-[(2R,3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 47491-70-3
• 化学式: C₁₄H₂₅NO₁₁
• 分子量: 383.353
• InChiKey: KFEUJDWYNGMDBV-LODBTCKLSA-N

物化性质

• 熔点：
  164 °C
• 沸点：
  805.5±65.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  198
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  β-D-galactopyranosyl-(1->4)-O-2-acetamido-2-deoxy-β-D-glucopyranose 在 galactose oxidase 、 氧气 、 catalase 、 horseradish peroxidase 作用下， 以 aq. phosphate buffer 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  [EN] DISACCHARIDE LINKER, DISACCHARIDE-SMALL MOLECULE DRUG CONJUGATE AND SUGAR CHAIN FIXED-POINT ANTIBODY-DRUG CONJUGATE, AND PREPARATION METHOD THEREFOR AND USE THEREOF
  [FR] LIEUR DISACCHARIDE, CONJUGUÉ MÉDICAMENT À PETITE MOLÉCULE-DISACCHARIDE ET CONJUGUÉ MÉDICAMENT-ANTICORPS À POINT FIXE DE CHAÎNE DE SUCRE, LEUR PROCÉDÉ DE PRÉPARATION ET LEUR UTILISATION
  [ZH] 二糖连接子、二糖-小分子药物偶联物以及糖链定点抗体-药物偶联物，其制备方法及用途

  摘要：

  本申请涉及一种二糖连接子、二糖-小分子药物偶联物以及糖链定点抗体-药物偶联物，其制备方法及用途。所述二糖连接子的结构如下式I所示。本发明提供了新型的定点定量抗体-药物偶联物形式，改善了抗体-药物偶联物的稳定性和细胞毒性。

  公开号：

  WO2022174834A1
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 β-glucosidase from Bifidobacterium bifidum 氢氟酸 、 sodium methylate 作用下， 以 吡啶 、 甲醇 、 乙二醇乙醚 、 phosphate buffer 为溶剂， 反应 10.0h， 生成 β-D-galactopyranosyl-(1->4)-O-2-acetamido-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  The efficient enzymatic synthesis of N-acetyllactosamine in an organic co-solvent

  摘要：

  In the presence of beta-galactosidase from Bifidobacterium bifidum, N-acetyllactosamine was synthesized in significantly enhanced yield compared with earlier routes. Different proportions of the (1-->4)- and (1-->6)-linked forms were obtained depending on the choice of enzyme and reaction conditions, viz. the nature of added organic co-solvent (20-80% of 2-ethoxy ethyl ether, trimethyl phosphate, or acetone). The beta-(1 --> 4)-linked disaccharide was the major product and the beta-(1-->6)-linked disaccharide was the minor product. With beta-galactosidases from P. multicolor, A. oryzae, B. longum the beta-(1 --> 6) linkage was exclusively synthesized. Procedures for optimising the yield of N-acetyllactosamine are discussed. An immobilized enzyme on a nylon powder column was used for the efficient recycling of enzyme and synthesizing the disaccharide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00063-x

文献信息

• CHEMOENZYMATIC SYNTHESIS OF HEPARIN AND HEPARAN SULFATE ANALOGS
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20140235575A1

  公开（公告）日：2014-08-21

  The present invention provides a one-pot multi-enzyme method for preparing UDP-sugars from simple sugar starting materials. The invention also provides a one-pot multi-enzyme method for preparing oligosaccharides from simple sugar starting materials.

  本发明提供了一种一锅多酶法，用于从简单糖起始材料制备UDP糖。该发明还提供了一种一锅多酶法，用于从简单糖起始材料制备寡糖。
• [EN] NOVEL GALACTOSIDE INHIBITOR OF GALECTINS<br/>[FR] NOUVEAU GALACTOSIDE COMME INHIBITEUR DE GALECTINES
  申请人：GALECTO BIOTECH AB

  公开号：WO2021001528A1

  公开（公告）日：2021-01-07

  The present invention relates to a D-galactopyranose compound of formula (1) wherein the pyranose ring is α-D-galactopyranose, and these compounds are high affinity galectin-1 and/or galectin 3 inhibitors for use in treatment of inflammation; fibrosis; scarring; keloid formation; aberrant scar formation; surgical adhesions; septic shock; cancer; metastasising cancers; autoimmune diseases, metabolic disorders; heart disease; heart failure; pathological angiogenesis; eye diseases; atherosclerosis; metabolic diseases; diabetes type I; diabetes type II; insulin resistance; Diastolic heart failure; asthma; liver disorders.

  本发明涉及一种式（1）的D-半乳糖吡喃糖类化合物，其中吡喃糖环为α-D-半乳糖吡喃糖，这些化合物是高亲和力的galectin-1和/或galectin 3抑制剂，用于治疗炎症；纤维化；瘢痕形成；瘢痕增生；异常瘢痕形成；手术粘连；脓毒性休克；癌症；转移性癌症；自身免疫疾病；代谢紊乱；心脏病；心力衰竭；病理性血管生成；眼部疾病；动脉粥样硬化；代谢性疾病；糖尿病I型；糖尿病II型；胰岛素抵抗；舒张期心力衰竭；哮喘；肝脏疾病。
• [EN] ALPHA-D-GALACTOSIDE INHIBITORS OF GALECTINS<br/>[FR] INHIBITEURS ALPHA-D-GALACTOSIDE DE GALECTINES
  申请人：GALECTO BIOTECH AB

  公开号：WO2016120403A1

  公开（公告）日：2016-08-04

  The present invention relates to a compound of the general formula (1). wherein the pyranose ring is a-D-galactopyranose, A is selected from The compound of formula (1) is suitable for use in a method for treating a disorder relating to the binding of a galectin, such as galectin-3 to a ligand in a mammal, such as a human. Furthermore the present invention concerns compounds for use in a method of treatment of a disorder relating to the binding of a galectin, such as galectin-3 to a ligand in a mammal, such as a human.

  本发明涉及一般式（1）的化合物。其中吡喃糖环为α-D-半乳糖，A选自。该式（1）化合物适用于治疗与在哺乳动物，如人类中的一个配体结合相关的疾病的方法。此外，本发明涉及用于治疗与在哺乳动物，如人类中的一个配体结合相关的疾病的方法的化合物。
• Novel Lactosamine Derivatives
  申请人：Dekany Gyula

  公开号：US20090234111A1

  公开（公告）日：2009-09-17

  The present invention provides novel lactosamine derivatives and related methods suitable for the preparation, including large-scale production, of N-acetyllactosamine, lactosamine, numerous lactosamine salts and a number of lactosamine-containing oligosaccharides. Preferred compounds are: (I) wherein R 1 is selected from the group consisting of optionally substituted acyl and optionally substituted alkyloxy-carbonyl; R 2 is selected from the group consisting of optionally substituted benzyl, optionally substituted benzhydryl, optionally substituted trityl, and optionally substituted naphthylmethyl (or R 2 is hydrogen in the formula to the left); R 3 is selected from the group consisting of optionally substituted C 1-5 -alkyl, optionally substituted heteroalkyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted C 2-6 -acyl, and hydrogen; and Q 1 and Q 2 are independently selected from the group consisting of electron withdrawing substituents.

  本发明提供了新颖的乳糖胺衍生物及相关方法，适用于制备N-乙酰乳糖胺、乳糖胺、多种乳糖胺盐和多种含乳糖胺的寡糖。首选化合物为：（I）其中R1选自可选择取代的酰基和可选择取代的烷氧羰基组成的群；R2选自可选择取代的苄基、可选择取代的苄基甲基、可选择取代的三苄基、可选择取代的萘甲基（或R2在左侧式中为氢）的群；R3选自可选择取代的C1-5烷基、可选择取代的杂原子烷基、可选择取代的杂环烷基、可选择取代的芳基、可选择取代的C2-6酰基和氢；Q1和Q2分别选自电子吸引取代基组成的群。
• [EN] NOVEL GALACTOSIDE INHIBITOR OF GALECTINS<br/>[FR] NOUVEL INHIBITEUR GALACTOSIDE DE GALECTINES
  申请人：GALECTO BIOTECH AB

  公开号：WO2016113335A1

  公开（公告）日：2016-07-21

  The present invention relates to a compound of the general formula (1). The compound of formula (1) is suitable for use in a method for treating a disorder relating to the binding of a galectin, such as galectin-3 to a ligand in a mammal, such as a human. Furthermore the present invention concerns a method for treatment of a disorder relating to the binding of a galectin, such as galectin-3 to a ligand in a mammal, such as a human.

  本发明涉及一种通式（1）的化合物。通式（1）的化合物适用于治疗与在哺乳动物（如人类）中的一个半乳凝集素（例如半乳凝集素-3）与配体结合有关的疾病的方法。此外，本发明涉及一种治疗与在哺乳动物（如人类）中的一个半乳凝集素（例如半乳凝集素-3）与配体结合有关的疾病的方法。