4-异硫氢酸苯基-Α-D-甘露糖苷 | 96345-79-8

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-异硫氢酸苯基-Α-D-甘露糖苷
• 英文名称: [p-isothiocyanato]-phenyl α-D-mannopyranoside
• 英文别名: p-isothiocyanato-phenyl α-D-mannopyranoside；4-Isothiocyanato-phenyl-α-D-mannopyranosid；α-D-mannopyranosyl-4-phenylisothiocyanate；α-D-mannopyranosylphenyl isothiocyanate；isothiocyanatophenyl alpha-D-mannoside；4-Isothiocyanatophenyl alpha-D-mannopyranoside；(2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-(4-isothiocyanatophenoxy)oxane-3,4,5-triol
• CAS: 96345-79-8
• 化学式: C₁₃H₁₅NO₆S
• 分子量: 313.331
• InChiKey: RWANFUZQWINQBY-BNDIWNMDSA-N

物化性质

• 熔点：
  180-181°C
• 沸点：
  577.5±50.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微）、乙酸乙酯（轻微）、甲醇（轻微、加热、超声处理

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  8

安全信息

• WGK Germany：
  3
• 海关编码：
  2932999099
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P501,P261,P270,P271,P264,P280,P284,P302+P352,P342+P311,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P310+P330,P304+P340+P311,P403+P233,P405
• 危险品运输编号：
  2811
• 危险性描述：
  H301+H331,H315,H319,H334,H335
• 储存条件：
  2-8°C

制备方法与用途

4-异硫氰酸苯α-D-甘露糖苷，这是一种有机异硫氰酸酯，常被用作制备新型糖蛋白的构建块和试剂［1］。

反应信息

• 作为反应物：
  描述：

  阿莫西林 、 4-异硫氢酸苯基-Α-D-甘露糖苷 生成 11-N-(α-D-Mannopyranosylphenylthiocarbamoyl)amoxicillin
  参考文献：
  名称：

  Hetfleisch-Stephan; Schunk; Rudiger, Pharmazie, 1994, vol. 49, # 2-3, p. 125 - 130

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯-Alpha-D-吡喃甘露糖苷 在 red. agent 作用下， 以 水 为溶剂， 生成 4-异硫氢酸苯基-Α-D-甘露糖苷
  参考文献：
  名称：

  Glycodendrimer synthesis without using protecting groups

  摘要：

  Oligoantennary neoglycoconjugates can act as powerful inhibitors of carbohydrate-protein interactions and thus serve as antiadhesives in carbohydrate-based adhesion systems. They were obtained by a procedure that doesn't require protecting groups. Various unprotected NCS-functionalized saccharides were coupled with oligoamines in aqueous solution. This versatile method is generally applicable to the synthesis of thiourea-bridged glycodendrimers. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00760-0

文献信息

• A ‘dual click’ strategy for the fabrication of bioselective, glycosylated self-assembled monolayers as glycocalyx models
  作者：Carsten Grabosch、Martin Kind、Yasmin Gies、Felix Schweighöfer、Andreas Terfort、Thisbe K. Lindhorst

  DOI：10.1039/c3ob40386f

  日期：——

  Solid surfaces decorated with specific saccharide patterns can serve as a model for the chemically and structurally highly complex glycocalyx of eukaryotic cells. Here we present an approach based on self-assembled monolayers on gold, which are built up in a three-step manner to provide a solid basis, a biorepulsive oligoethylene glycol part, and a specific carbohydrate terminus in a modular way. Of the different reaction sequences, the one with two consecutive ‘click reactions’ (the copper(I)-catalysed 1,3-dipolar cycloaddition of alkynes with azides and the thiourea-bridging of isothiocyanates with amines) directly ‘on SAM’ results in the densest layers, as demonstrated by infrared absorption reflection spectroscopy and ellipsometry. As a ‘real life’ test, the surfaces obtained this way were used for bacterial adhesion experiments. Here the biorepulsivity of the middle part of the SAMs as well as specific binding to the carbohydrate termini could be clearly demonstrated.

  用特定糖图案装饰的固体表面可以作为化学和结构高度复杂的真核细胞糖萼的模型。在这里，我们提出了一种基于金上自组装单层的方法，该方法以三步方式构建，以模块化方式提供坚实的基础、生物排斥性的低聚乙二醇部分和特定的碳水化合物末端。在不同的反应序列中，具有两个连续“点击反应”（铜 (I) 催化的炔烃与叠氮化物的 1,3-偶极环加成反应以及异硫氰酸酯与胺的硫脲桥联反应）的反应序列直接正如红外吸收反射光谱和椭圆光度法所证明的那样，SAM™ 上的结果是最致密的层。作为“现实生活”测试，通过这种方式获得的表面用于细菌粘附实验。这里可以清楚地证明 SAM 中部的生物排斥性以及与碳水化合物末端的特异性结合。
• NANOPARTICLE COATED WITH LIGAND INTRODUCED WITH LONG HYDROPHOBIC CHAIN AND METHOD FOR PREPARING SAME
  申请人：Jeong Jae Min

  公开号：US20140199235A1

  公开（公告）日：2014-07-17

  The present invention relates to a nanoparticle having a linker connected to a long alkane or alkene chain, and a method for preparing the nanoparticle. The alkyl chain of C 10-30 introduced with a ligand of the present invention can be coated on a hydrophobic nanoparticle through a noncovalent bond, enabling easy introduction of various ligands to the nanoparticle, and the nanoparticle having various functional groups prepared using the method can be applied to fluorescent detection, MRI, raman spectroscopy, optical detection, PET, SPECT, or gamma image device, and the ligand of the visualization agents can be modified to be used for new vessels detection, cancer cell detection, immunocyte detection, hepatocyte detection, cell death detection, and gene detection.

  本发明涉及一种纳米颗粒，其具有连接到长链烷基或烯基的连接剂，以及制备该纳米颗粒的方法。通过引入本发明的配体的C10-30烷基链可以通过非共价键涂覆在疏水性纳米颗粒上，从而便于引入各种配体到纳米颗粒中。使用该方法制备的具有各种功能基团的纳米颗粒可以应用于荧光检测、MRI、拉曼光谱、光学检测、PET、SPECT或伽马成像装置，并且可将可视化剂的配体修改以用于新血管检测、癌细胞检测、免疫细胞检测、肝细胞检测、细胞死亡检测和基因检测。
• Influencing Receptor−Ligand Binding Mechanisms with Multivalent Ligand Architecture
  作者：Jason E. Gestwicki、Christopher W. Cairo、Laura E. Strong、Karolyn A. Oetjen、Laura L. Kiessling

  DOI：10.1021/ja027184x

  日期：2002.12.1

  features of a multivalent ligand that determine whether it will function as an inhibitor or effector. We envisioned that, by altering multivalent ligand architecture, ligands with preferences for different binding mechanisms would be generated. To this end, a series of 28 ligands possessing structural diversity was synthesized. This series provides the means to explore the effects of ligand architecture

  多价配体可以作为生物过程的抑制剂或效应物。多价配体-受体相互作用的高功能亲和力可以产生有效的抑制活性。然而，效应子功能不仅受表观亲和力的影响，还受其他因素的影响，包括配体聚集受体的能力。关于决定它是作为抑制剂还是效应物起作用的多价配体的分子特征知之甚少。我们设想，通过改变多价配体结构，将产生偏好不同结合机制的配体。为此，合成了一系列具有结构多样性的 28 个配体。本系列提供了探索配体结构对模型蛋白凝集素伴刀豆球蛋白 A (Con A) 抑制和聚类影响的方法。变化的结构参数包括支架形状、大小、化合价和结合元素的密度。我们发现具有某些结构的配体是有效的抑制剂，但其他的则介导受体聚集。具体而言，高分子量、多分散多价配体是 Con A 结合的有效抑制剂，而由开环复分解聚合产生的线性寡聚配体具有有利于聚类的结构特性。多价配体的形状也会影响受体聚类的特定方面。这些包括受体聚集的速率、簇中受体的数量、和
• Vectors for dna delivery
  申请人：——

  公开号：US20030207400A1

  公开（公告）日：2003-11-06

  The present invention pertains to novel products suitable for use as gene delivery systems in which nucleic acid is linked to a ligand in order to facilitate delivery of the nucleic acid to a target cell or sub-cellular compartment via uptake of the ligand. More particularly, the present invention pertains to vectors comprising: (a) a double stranded DNA (dsDNA) having at least one target sequence; and, (b) a chimeric molecule comprising: (i) a sequence specific polyamide (SSP) moiety bound non-covalently to said target sequence; and, (ii) a ligand moiety linked covalently to said sequence specific polyamide. The present invention also pertains to compositions comprising such chimeric molecules and vectors; methods for making such chimeric molecules and vectors; and methods of using such chimeric molecules and vectors, e.g., to deliver nucleic acid vectors to cells or sub-cellular compartments.

  本发明涉及新型产品，适用于用作基因传递系统，其中核酸与配基连接，以便通过配基的摄取促进核酸传递到目标细胞或亚细胞区域。更具体地，本发明涉及包括：（a）至少具有一个目标序列的双链DNA（dsDNA）；以及（b）包括的嵌合分子：（i）与所述目标序列非共价结合的序列特异性聚酰胺（SSP）基团；以及（ii）与所述序列特异性聚酰胺共价连接的配基基团。本发明还涉及包含这种嵌合分子和向量的组合物；制备这种嵌合分子和向量的方法；以及使用这种嵌合分子和向量的方法，例如将核酸向量传递到细胞或亚细胞区域。
• Electrobiochemical method, system and electrodes for determination of a member of a recognition pair
  申请人：YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM

  公开号：EP0668502A2

  公开（公告）日：1995-08-23

  An electrobiochemical system for the determination of the presence and optionally concentration of an analyte in a liquid medium, the system comprising an electrode having immobilized thereon a member of a recognition pair, the other member of said pair being said analyte, the presence of said analyte in the medium resulting in formation of a pair complex, being a complex between said immobilized member and said analyte; the system further comprising redox molecules capable of changing their redox state by accepting electrons from or donating electrons to the electrode; the formation of the pair complex on the electrode bringing a change in the electrical response of the system, whereby the presence and optionally the concentration of said analyte in the medium can be determined.

  一种用于测定液体介质中分析物的存在和浓度的电生化系统，该系统包括一个电极，该电极上固定有识别对的一个成员，所述识别对的另一个成员是所述分析物，介质中所述分析物的存在导致形成识别对复合物，即所述固定成员与所述分析物之间的复合物；该系统还包括氧化还原分子，能够通过从电极接受电子或向电极提供电子来改变其氧化还原状态；在电极上形成的配对复合物会导致系统的电响应发生变化，从而可以确定介质中是否存在所述分析物，并可选择确定所述分析物的浓度。