[2-isothiocyanato]-ethyl α-D-mannopyranoside | 191731-50-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-isothiocyanato]-ethyl α-D-mannopyranoside
• 英文别名: 2-isothiocyanatoethyl α-D-mannopyranoside；2-isothiocyanatoethyl-α-D-mannopyranoside；(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(2-isothiocyanatoethoxy)oxane-3,4,5-triol
• CAS: 191731-50-7
• 化学式: C₉H₁₅NO₆S
• 分子量: 265.287
• InChiKey: SJFRRNJRVVCLSF-DFTQBPQZSA-N

物化性质

• 沸点：
  514.0±50.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,8-二氨基-3,6-二氧杂辛烷 、 [2-isothiocyanato]-ethyl α-D-mannopyranoside 以 水 为溶剂， 以98%的产率得到1-[2-((2S,3S,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-3-{2-[2-(2-{3-[2-((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-thioureido}-ethoxy)-ethoxy]-ethyl}-thiourea
  参考文献：
  名称：

  多价配体结构影响受体-配体结合机制

  摘要：

  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

  DOI：

  10.1021/ja027184x
• 作为产物：
  描述：

  硫光气 、 2-aminoethyl α-D-mannopyranoside 以 乙醇 、 水 为溶剂， 反应 2.0h， 以93%的产率得到[2-isothiocyanato]-ethyl α-D-mannopyranoside
  参考文献：
  名称：

  Surface Functionalization of Nanomaterials with Dendritic Groups: Toward Enhanced Binding to Biological Targets

  摘要：

  A diverse array of nanomaterials ranging from polymer assemblies to nanoparticles has been under development for biomedical applications in recent years. A key aspect of these applications is the ability to target the materials to the desired locations in vivo by exploiting their size or through the conjugation of active targeting groups. While nanoscale scaffolds may provide advantages such as the multivalent presentation of targeting ligands, the binding of these ligands may also be inhibited by interfering polymer chains at their surfaces. This aspect was investigated here by preparing poly(butadiene-b/ock-ethylene oxide) vesicles and dextran-coated iron oxide nanoparticles functionalized with dendritic and nondendritic displays of mannose, a well-known multivalent ligand. The binding of these systems to the mannose-binding protein Concanavalin A was compared using a hemagglutination assay. It was found that the dendritic systems exhibited 1-2 orders of magnitude enhancement in binding affinity relative to the nondendritic displays. This result is attributed to the ability of the dendritic groups to overcome steric inhibition by polymer chains at the material surface and also to the presentation of ligands in localized clusters. It is anticipated that these results should be applicable to a wide range of nanomaterials with polymers at their surfaces and that the method by which biological ligands are conjugated to the surfaces of nanoparticles and polymer assemblies should be carefully considered.

  DOI：

  10.1021/ja807220u

文献信息

• NOVEL AMPHIPHILIC CYCLODEXTRIN DERIVATIVES
  申请人：Defaye Jacques

  公开号：US20100093662A1

  公开（公告）日：2010-04-15

  The present invention relates to cyclodextrins having the following formula (I): to nanostructures comprising them, to processes for preparing them, to the use thereof, and also to compositions comprising them.

  本发明涉及具有以下化学式(I)的环糊精，以及包含它们的纳米结构，制备它们的方法，其用途，以及含有它们的组合物。
• Mannose‐BSA Conjugates: Comparison Between Commercially Available Linkers in Reactivity and Bioactivity
  作者：Masayuki Izumi、Shigeyoshi Okumura、Hideya Yuasa、Hironobu Hashimoto

  DOI：10.1081/car-120023475

  日期：2003.1.8

  Mannosyl ethanolamine and BSA were conjugated together by their amino groups with various homobifunctional cross-linker reagents: disuccinimidyl carbonate (DSC), disuccinimidyl glutarate (DSG), disuccinimidyl suberate (DSS), ethylene glycolbis-(succinimidylsuccinate) (EGS), 1,5-difluoro-2,4-dinitrobenzene (DFDNB), diethyl squarate (DES), and thiophosgene (TP). The resulting mannose-BSA conjugates were subjected to an enzyme-linked lectin assay (ELLA) to investigate their affinity to concanvalin A (ConA). With these results, the seven linkers were evaluated on the basis of five criteria, i.e., cost, reactivity, sugar loading, homogeneity, and affinity to ConA. Thus, DSS, DFDNB, and DES seemed to have advantages over the other cross-linking reagents.
• Glycodendrimer synthesis without using protecting groups
  作者：Christoffer Kieburg、Thisbe K. Lindhorst

  DOI：10.1016/s0040-4039(97)00760-0

  日期：1997.6

  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.
• NOUVEAUX DÉRIVÉS DE CYCLODEXTRINES AMPHI PHILES
  申请人：Centre National De La Recherche Scientifique-CNRS

  公开号：EP2044128A2

  公开（公告）日：2009-04-08
• [EN] NOVEL AMPHIPHILIC CYCLODEXTRIN DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS DE CYCLODEXTRINES AMPHI PHILES
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2008009831A2

  公开（公告）日：2008-01-24

  [EN] The present invention relates to cyclodextrins having the following formula (I): to nanostructures comprising them, to processes for preparing them, to the use thereof, and also to compositions comprising them.
  [FR] La présente invention concerne des cyclodextrines de Formule (I) suivante : des nanostructures les comprenant, leurs procédés de préparation, l'utilisation de ceux-ci, ainsi que des compositions les comprenant.