2-acetamido-6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranoside | 33289-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranoside
• 英文别名: 2-acetamido-6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranose；6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetamido-2-deoxy-D-glucopyranose；GlcNAcβ(1->6)GlcNAc；2-Acetamido-6-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-D-glucopyranose；2-Acetamido-6-O-(2-acetamido-2-deoxy-B-D-glucopyra；N-[(3R,4R,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,4,5-trihydroxyoxan-3-yl]acetamide
• CAS: 33289-65-5
• 化学式: C₁₆H₂₈N₂O₁₁
• 分子量: 424.405
• InChiKey: ZNYQSCCJIAFAQX-LIQXALPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  207
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-acetamido-6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranoside 在 citrate-phosphate buffer 、 β-N-acetylhexosaminidase from Aspergillus oryzae CCF 1066 作用下， 反应 3.0h， 生成 D-GlcNAc
  参考文献：
  名称：

  使用β- N-乙酰己糖胺酶对2-乙酰氨基-2-脱氧-D-甘露吡喃糖二糖的酶鉴别

  摘要：

  摘要：米曲霉中的β- N-乙酰己糖胺酶选择性地区分了二糖GlcNAcβ（14）GlcNAc（1）和GlcNAcβ（14）ManNAc（2）的混合物。N，N'-二乙酰基壳二糖（1）被β- N-乙酰基己糖胺酶选择性水解，而其C-2差向异构体（2）则完全抵抗酶水解。用GalNAcβ（14）GlcNAc（3）和GalNAcβ（14）ManNAc（4）也观察到类似的区分。土曲霉，黄曲霉的β- N-乙酰己糖胺酶，牛肾和牛附睾显示出相同的选择性，而来自大豆酱油杆菌，番茄酱油杆菌，巴西青霉，草酸假单胞菌，P。funiculosum，多色的P.，Talaromyces flavus和杰克豆的酶水解了两种类型的双糖。米曲霉CCF 1066的β- N-乙酰基己糖胺酶的分子模型以及两种类型的双糖的对接实验表明，ManNAc残基导致双糖分子变形，从而导致与Trp 482发生空间冲突，从而导致恶唑啉鎓过渡态的稳定性降低通过扩展活动站点中Asp

  DOI：

  10.1002/adsc.200303002
• 作为产物：
  描述：

  D-GlcNAc 生成 2-acetamido-6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranoside
  参考文献：
  名称：

  DEFAYE, JACQUES;GADELLE, ANDREE;PEDERSEN, CHRISTIAN, CARBOHYDR. RES., 186,(1989) N, C. 177-188

  摘要：

  DOI：

文献信息

• Protecting Group Free Glycosidations Using <i>p</i>-Toluenesulfonohydrazide Donors
  作者：Anna V. Gudmundsdottir、Mark Nitz

  DOI：10.1021/ol801232f

  日期：2008.8.21

  N'-Glycopyranosylsulfonohydrazides are introduced as glycosyl donors for protecting group free synthesis of O-glycosides, glycosyl azides, and oxazolines. Mono- and disaccharides containing a reducing terminal N-acetylglucosamine residue were condensed with p-toluenesulfonylhydrazide to give the desired beta- d-pyranose donors. These donors can be activated with NBS and then glycosidated with the desired

  引入N'-甘露糖基磺酰肼作为糖基供体，用于保护O-糖苷，糖基叠氮化物和恶唑啉的无基团合成。将含有还原性末端N-乙酰氨基葡糖残基的单糖和二糖与对甲苯磺酰肼缩合，得到所需的β-d-吡喃糖供体。这些供体可以用NBS活化，然后用所需的醇糖基化或转化为恶唑啉或糖基叠氮化物。
• Kinetic control of regioselectivity in glycosidase-catalysed disaccharide synthesis: preparation of 2-acetamido-4-O-(2-acetamido-2-deoxy-β-<scp>D</scp>-glucopyranosyl)-2-deoxy-<scp>D</scp>-glucopyranose (N,n′-diacetylchitobiose) and 2-acetamido-6-O-(2-acetamido-2-deoxy-β-<scp>D</scp>-glucopyranosyl)-2-deoxy-<scp>D</scp>-glucopyranose
  作者：Suddham Singh、John Packwood、David H. G. Crout

  DOI：10.1039/c39940002227

  日期：——

  During transfer of the N-acetyl-β-D-glucosaminyl (2-acetamido-2-deoxy-β-D-glucopyranosyl) residue from p-nitrophenyl N-acetyl-β-D-glucosaminide (p-nitrophenyl N-2-deoxy-β-D-glucopyranoside) on to N-acetyl-D-glucosamine (2-acetamido-2-deoxy-D-glucopyranose) catalysed by the N-acetylhexosaminidase from Aspergillus oryzae, the major isomer formed was found to depend on the time course of the reaction, 1 → 4 transfer predominating while the p-nitrophenyl glycoside was available as donor, but 1 → 6 transfer when the initially-formed 1 → 4 product took over as donor, results that could be interpreted in terms of a constant regioselectivity modulated by selective hydrolysis of the products.

  在通过来自黄曲霉的N-乙酰氨基己糖苷酶催化，将p-硝基苯基N-乙酰-β-D-氨基葡萄糖苷（p-硝基苯基N-2-脱氧-β-D-葡萄糖苷）的N-乙酰-β-D-氨基葡萄糖基团转移到N-乙酰-D-氨基葡萄糖（2-乙酰氨基-2-脱氧-D-葡萄糖）时，形成的主要异构体的种类依赖于反应的时间进程。当p-硝基苯基糖苷作为供体时，以1→4转移为主，但当最初生成的1→4产物作为供体时，则以1→6转移为主。这些结果可以根据一个通过选择性水解产物而调节的恒定区域选择性来解释。
• Hydrogen fluoride-catalyzed formation of glycosides. Preparation of methyl 2-acetamido-2-deoxy-β-d-gluco- and -β-d-galacto-pyranosides, and of β-(1→6)-linked 2-acetamido-2-deoxy-d-gluco- and -d-galacto-pyranosyl oligosaccharides
  作者：Jacques Defaye、Andrée Gadelle、Christian Pedersen

  DOI：10.1016/0008-6215(89)84033-9

  日期：1989.3

  Dissolution of 2-acetamido-2-deoxy-d-glucose (1) or -d-galactose (2) in anhydrous hydrogen fluoride, followed by addition of methanol, gave stereospecifically the corresponding methyl β-d-glycopyranosides 7 and 8. When solutions of 1 or 2 in hydrogen fluoride were slowly evaporated, mixtures of exclusively β-d-(1→6)-linked di- to hexa-saccharides containing 2-acetamido-2-deoxy-glucosyl (9) and -galactosyl

  将2-乙酰氨基-2-脱氧-d-葡萄糖（1）或-d-半乳糖（2）溶解在无水氟化氢中，然后加入甲醇，立体定向地得到相应的甲基β-d-吡喃葡萄糖苷7和8。缓慢蒸发1或2在氟化氢中的溶液，仅包含2-乙酰胺基2-脱氧葡萄糖基（9）和-半乳糖基（10）的β-d-（1→6）连接的二糖至六糖的混合物）残留物；用凝胶渗透色谱法分离得到纯产物。当在适当条件下处理几丁质溶液时，也获得了化合物7和9。
• Protein particles for therapeutic and diagnostic use
  申请人：——

  公开号：US20020142046A1

  公开（公告）日：2002-10-03

  Albumin particles in the nanometer and micrometer size range in an aqueous suspension are rendered stable against resolubilization without the aid of a cross-linking agent and witout denaturation, by the incorporation of a stabilizing agent in the particle composition. Stabilizing agents disclosed include reducing agents, oxdizing agents, hydrogen-accepting molecules, high molecular weight polymers, and sulfur-containing ring compounds. Also disclosed are fibrinogen-coated particles, cross-linked or non-cross-linked, and their use as co-aggregants with platelets and with themselves for purposes of shortening bleeding time and enhancing the effect of thrombin.

  通过在颗粒组合物中加入稳定剂，可使水悬浮液中纳米和微米大小的白蛋白颗粒在不借助交联剂和不发生变性的情况下稳定地防止溶解。已公开的稳定剂包括还原剂、氧化剂、氢接受分子、高分子量聚合物和含硫环化合物。此外，还公开了交联或非交联的纤维蛋白原涂层微粒，以及它们作为与血小板和自身的共聚物的用途，以达到缩短出血时间和增强凝血酶效果的目的。
• DEFAYE, J.;GADELLE, A.;PEDERSEN, C., CHITIN AND CHITOSAN: SOURCES, CHEM., BIOCHEM., PHYS. PROP. AND APPL.: PRO+
  作者：DEFAYE, J.、GADELLE, A.、PEDERSEN, C.

  DOI：——

  日期：——