2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-2-acetamido-2-deoxy-D-glucopyranoside | 29709-56-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-2-acetamido-2-deoxy-D-glucopyranoside
• 英文别名: β-D-GlcpNAc-(1->3)-D-GlcpNAc；2-Acetamido-3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranose；O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-3)-2-acetamido-2-deoxy-α/β-D-glucopyranose；GlcNAc(b1-3)GlcNAc；N-[(2R,3R,4R,5S,6R)-2-[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 29709-56-6
• 化学式: C₁₆H₂₈N₂O₁₁
• 分子量: 424.405
• InChiKey: FJGXDMQHNYEUHI-CBTAGEKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.11
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  207.27
• 氢给体数：
  8.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2-acetamido-4,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 在 palladium on activated charcoal 吡啶 、 氢气 、 sodium methylate 、 正丁胺 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 52.0h， 生成 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-2-acetamido-2-deoxy-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Linear and Branched Regioisomeric Chitooligosaccharides as Potential Mimetics of Natural Oligosaccharide Ligands of Natural Killer Cells NKR-P1 and CD69 Lectin Receptors

  摘要：

  制备了β(1→3)糖苷键的N-乙酰葡萄糖二聚体13的同分异构体和具有β(1→4)和β(1→3)糖苷键的分支寡糖25的类似物，作为天然寡糖配体激活自然杀伤细胞(NK细胞)的凝集素受体NKR-P1A和CD69的潜在模拟物进行测试。讨论了NKR-P1凝集素受体对其天然配体有效模拟物的结构要求。观察到分支三糖25与受体CD69的显著结合活性。

  DOI：

  10.1135/cccc20041781

文献信息

• Direct formation of β-glycosides of N-acetyl glycosamines mediated by rare earth metal triflates
  作者：Helle Christensen、Mira Steinicke Christiansen、Jette Petersen、Henrik Helligsø Jensen

  DOI：10.1039/b807064d

  日期：——

  microwave conditions were needed to attain acceptable yields with less reactive, carbohydrate based glycosyl acceptors. The protocol developed was applied to provide the first example of direct chemical formation of a disaccharide using both GlcNAc as a glycosyl donor and acceptor. The alpha-acetate donor was found to be significantly less reactive than the corresponding beta-anomer necessitating higher

  使用过乙酰化的β-GlcNAc和β-GalNAc作为供体，开发了一种直接，温和且有效的方案，用于制备N-乙酰基氨基葡萄糖（GlcNAc）和N-乙酰基半乳糖胺（GalNAc）的β-糖苷。发现所有筛选的稀土金属三氟甲磺酸盐启动子均能促进糖基化，而Sc（OTf）（3）的反应速率则更高。发现简单的醇糖基化可在回流的二氯甲烷中顺利进行，而在微波条件下需要较高的温度才能获得可接受的收率，且反应性较低的基于碳水化合物的糖基受体。应用所开发的方案，以提供同时使用GlcNAc作为糖基供体和受体的二糖直接化学形成的第一个例子。发现α-乙酸酯供体比相应的β-端基异构体显着更低的反应性，这需要更高的反应温度，在该温度下发现发生糖苷的异构化。可以确定，仅在Sc（OTf）（3）和乙酸都存在的情况下才会发生异化反应。
• [EN] ACHOLETIN BIOPOLYMERS AND METHODS FOR ENZYMATIC SYNTHESIS<br/>[FR] BIOPOLYMÈRES D'ACHOLÉTINE ET PROCÉDÉS DE SYNTHÈSE ENZYMATIQUE
  申请人：[en]THE UNIVERSITY OF BRITISH COLUMBIA

  公开号：WO2022256920A1

  公开（公告）日：2022-12-15

  Provided herein are β-1,3-linked biopolymers (acholetin polysaccharides). Furthermore, provided herein are enzymatic methods and systems for producing β-1,3-linked oligosaccharides and polysaccharides using β-1,3-N-acetylglucosaminide phosphorylase (Acholetin phosphorylase (AchP)). The AchP was sourced from the genome of the cell wall-less Mollicute bacterium, Acholeplasma laidlawii and was found to synthesize β-1,3-linked N-acetylglucosamine (GlcNAc) or N-acetylgalactosamine (GalNAc) oligomers using the donor, α-N-acetylglucosamine 1-phosphate (GlcNAc1-P) or N-acetylgalactosamine 1-phosphate (GalNAc1-P).