2-acetamido-2-deoxy-6-O-β-D-galactopyranosyl-D-galactose

• 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-6-O-β-D-galactopyranosyl-D-galactose
• 英文别名: β-D-Gal-(1->6)-D-GalNAc；Gal-(β1→6)GalNAc；2-Acetamido-2-deoxy-6-O-beta-D-galactopyranosyl-D-galactopyranose；N-[(3R,4R,5R,6R)-2,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-3-yl]acetamide
• 化学式: C₁₄H₂₅NO₁₁
• 分子量: 383.353
• InChiKey: ACKXCNXSQYSCQN-UUHITYSKSA-N

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

• 作为产物：
  描述：

  Lactose 、 2-乙酰氨基-2-脱氧-D-吡喃半乳糖 以 乙腈 为溶剂， 反应 15.0h， 以14 mg的产率得到2-acetamido-2-deoxy-6-O-β-D-galactopyranosyl-D-galactose
  参考文献：
  名称：

  使用来自圆形芽孢杆菌的β-D-半乳糖苷酶方便地合成β-D-半乳糖基二糖衍生物。

  摘要：

  β-D-Gal-（1-> 4）-β-D-GlcNAc-OC6H4NO2-p（对硝基苯基N-乙酰基-β-乳糖苷）和β-D-Gal-（1-> 6）- β-D-GlcNAc-OC6H4NO2-p（对硝基苯基N-乙酰基-β-异乳糖胺）是通过乳糖和对硝基苯基2-乙酰氨基-2-脱氧葡萄糖吡喃糖苷进行区域选择性合成的，其中β-D-半乳糖苷酶通过芽孢杆菌回旋菌并通过控制反应体系中有机溶剂的浓度。当有机溶剂的浓度较高时，仅形成（1→4）连接的二糖，而低浓度时生成（1→6）连接的异构体。酶进一步利用转糖基化作用导致β-D-Gal-（1→4）-D-GalNAc和β-D-Gal-（1→4）-β-D-的区域选择性形成GalNAc-OC6H4NO2-p。用酵素

  DOI：

  10.1016/0008-6215(83)85010-1

文献信息

• A convenient synthesis of β-d-galactosyl disaccharide derivatives using the β-d-galactosidase from Bacillus circulans
  作者：Taichi Usui、Shinobu Kubota、Hiroshi Ohi

  DOI：10.1016/0008-6215(83)85010-1

  日期：1993.6

  (p-nitrophenyl N-acetyl-beta-isolactosaminide) were regioselectively synthesized from lactose and p-nitrophenyl 2-acetamido-2-deoxy-glucopyranoside, employing transglycosylation by the beta-D-galactosidase from Bacillus circulans and by controlling the concentration of organic solvent in the reaction system. The (1-->4)-linked disaccharide was formed exclusively when the concentration of organic solvent was high

  β-D-Gal-（1-> 4）-β-D-GlcNAc-OC6H4NO2-p（对硝基苯基N-乙酰基-β-乳糖苷）和β-D-Gal-（1-> 6）- β-D-GlcNAc-OC6H4NO2-p（对硝基苯基N-乙酰基-β-异乳糖胺）是通过乳糖和对硝基苯基2-乙酰氨基-2-脱氧葡萄糖吡喃糖苷进行区域选择性合成的，其中β-D-半乳糖苷酶通过芽孢杆菌回旋菌并通过控制反应体系中有机溶剂的浓度。当有机溶剂的浓度较高时，仅形成（1→4）连接的二糖，而低浓度时生成（1→6）连接的异构体。酶进一步利用转糖基化作用导致β-D-Gal-（1→4）-D-GalNAc和β-D-Gal-（1→4）-β-D-的区域选择性形成GalNAc-OC6H4NO2-p。用酵素
• Modulation of the P2Y2 receptor pathway
  申请人：P2-Science APS

  公开号：EP2036567A2

  公开（公告）日：2009-03-18

  The present invention relates to the field of regulating the activity of the purinergic receptors for the modulation of the vascular tone, particularly for the purpose of treatment of haemodynamic conditions by overriding of vasoconstriction activity, such as increases in sympathic vasoconstriction. Modulators, such as UTP analogues as described herein are preferably specific for P2Y2. Compounds capable of stimulating the P2Y2 receptor are suitable for the treatment or prevention wherein inhibition of vasoconstriction activity is desirable such as hypertension and hypertension relates disorders or diseases, whereas compound capable of counteracting the activity of the P2Y2 receptor are suitable for the treatment of or prevention wherein inhibition of vasodilatation is desirable.

  本发明涉及调节嘌呤能受体活性以调节血管张力的领域，特别是通过抑制血管收缩活性（如交感血管收缩增加）来治疗血流动力学疾病。调节剂，如本文所述的UTP 类似物，最好对 P2Y2 具有特异性。能够刺激 P2Y2 受体的化合物适用于治疗或预防需要抑制血管收缩活性的疾病，如高血压和高血压相关失调或疾病，而能够抵消 P2Y2 受体活性的化合物适用于治疗或预防需要抑制血管舒张的疾病。
• Compounds that bind P2Y2 or P2Y1 receptors
  申请人：——

  公开号：US20040116339A1

  公开（公告）日：2004-06-17

  The invention provides peptides and compounds that can bind to P2Y 2 receptors that are useful for modulating the secretion of mucus within mucosal surfaces.

  本发明提供了能与 P2Y 2 受体，可用于调节粘膜表面的粘液分泌。
• Highly efficient enzymatic synthesis of Galβ-(1→3)-GalNAc and Galβ-(1→3)-GlcNAc in ionic liquids
  作者：Carlos Bayón、Álvaro Cortés、José Berenguer、María J. Hernáiz

  DOI：10.1016/j.tet.2013.04.015

  日期：2013.6

  Ionic liquids (ILs) have emerged as an alternative to conventional organic media due to their high thermal and chemical stability, negligible vapour pressure, non-flammability and easy recycling. In this context, this work assesses the catalytic activity of a beta-galactosidase from Bacillus circulans ATCC 31382 (beta-Gal-3-NTag) in the synthesis of beta-(1 -> 3)-galactosides using different ILs. A noticeably increase in activity, retaining total regioselectivity was found in the synthetic behaviour of B. circulans beta-galactosidase in ILs as co-solvents and using a 1:5 molar ratio of donor (pNP-beta-Gal):acceptor (GlcNAc or GalNac). Yields up to 97% of beta-(1 -> 3) with different ILs were found. These reactions take place without noticeable hydrolytic activity and with total regioselectivity, representing a considerable improvement over the use of aqueous buffer or conventional organic solvents. Furthermore, reaction scaling up and IL recovery and recycling are feasible without losing catalytic action. Molecular modelling studies performed predict a three-dimensional interaction at the active centre between the acceptor and the water-IL mixture, which could explain the results obtained. (C) 2013 Elsevier Ltd. All rights reserved.
• COMPOUNDS THAT BIND P2Y sb 2 /sb OR P2Y sb 1 /sb RECEPTORS
  申请人：KIMBERLY-CLARK WORLDWIDE, INC.

  公开号：EP1592436A2

  公开（公告）日：2005-11-09