Galβ1-4GlcNAcβ-CH2CH2NH2 | 799854-49-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Galβ1-4GlcNAcβ-CH2CH2NH2
• CAS: 799854-49-2
• 化学式: C₁₆H₃₀N₂O₁₁
• 分子量: 426.421
• InChiKey: RZBMTRLFFCHAEF-NSSUFJHZSA-N

物化性质

• 沸点：
  804.8±65.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.27
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  213.42
• 氢给体数：
  8.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Galβ1-4GlcNAcβ-CH2CH2NH2 、 4-戊烯酐 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 以3.12 g的产率得到N-(2-(((2R,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)ethyl)pent-4-enamide
  参考文献：
  名称：

  Sialoside Analogue Arrays for Rapid Identification of High Affinity Siglec Ligands

  摘要：

  The siglec family of sialic acid binding proteins participates in diverse I cell surface biology that includes regulation of immune cell signaling and the interaction of neuronal cells with glial cells. The weak intrinsic affinity of the natural sialoside ligands has hampered the development of synthetic ligand based probes needed to elucidate their roles in siglec function. In this report, we describe a glycan microarray comprising a library of 9-acyl-substituted sialic acids incorporated into sialosides containing the Neu5Aca2-3Gal and Neu5Aca2-6Gal linkages commonly recognized by the siglecs. The array is demonstrated to exhibit utility for detecting 9-acyl substituents that increase the affinity of siglecs for their ligands. Substituents that increase affinity are anticipated to be useful for the design of high affinity ligand based probes of siglec function.

  DOI：

  10.1021/ja801052g
• 作为产物：
  描述：

  2-azidoethyl (β-D-galactopyranosyl)-(1->4)-O-2-acetamido-2-deoxy-β-D-glucopyranoside 在 三甲基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 Galβ1-4GlcNAcβ-CH2CH2NH2
  参考文献：
  名称：

  CD22 Ligands on a Natural N-Glycan Scaffold Efficiently Deliver Toxins to B-Lymphoma Cells

  摘要：

  CD22 is a sialic acid-binding immunoglobulin-like lectin (Siglec) that is highly expressed on B-cells and B cell lymphomas, and is a validated target for antibody and nanoparticle based therapeutics. However, cell targeted therapeutics are limited by their complexity, heterogeneity, and difficulties in production. We describe here a chemically defined natural N-linked glycan scaffold that displays high affinity CD22 glycan ligands and outcompetes the natural ligand for the receptor, resulting in single molecule binding to CD22 and endocytosis into cells. Binding affinity is increased by up to 1500-fold compared to the monovalent ligand, while maintaining the selectivity for hCD22 over other Siglecs. Conjugates of these multivalent ligands with auristatin and saporin toxins are efficiently internalized via hCD22 resulting in killing of B-cell lymphoma cells. This single molecule ligand targeting strategy represents an alternative to antibody- and nanoparticle-mediated approaches for delivery of agents to cells expressing CD22 and other Siglecs.

  DOI：

  10.1021/jacs.7b03208

文献信息

• Synthesis of biotinylated keratan sulfate repeating disaccharides
  作者：Naoko Takeda、Jun-ichi Tamura

  DOI：10.1080/09168451.2014.877834

  日期：2014.1.2

  We synthesized four types of keratan and keratan sulfate repeating disaccharides containing non-sulfate, Galβ1-4GlcNAcβ, and three types of sulfates, Gal6Sβ1-4GlcNAcβ, Galβ1-4GlcNAc6Sβ, and Gal6Sβ1-4GlcNAc6Sβ in an efficient and stereo-controlled manner. These disaccharides were conjugated with biotin via a hydrophilic linker at the reducing terminal.

  我们以一种高效和立体控制的方式合成了四种类型的角质蛋白和角质蛋白硫酸盐重复二糖，其中包含非硫酸盐的Galβ1-4GlcNAcβ和三种硫酸盐，Gal6Sβ1-4GlcNAcβ、Galβ1-4GlcNAc6Sβ和Gal6Sβ1-4GlcNAc6Sβ。这些二糖通过一个亲水连接剂与生物素结合在还原末端。
• Chemo-enzymatic synthesis of functionalized oligomers of N-acetyllactosamine glycan derivatives and their immobilization on biomaterial surfaces
  作者：Kathrin Adamiak、Thorsten Anders、Manja Henze、Helmut Keul、Martin Möller、Lothar Elling

  DOI：10.1016/j.molcatb.2012.02.002

  日期：2012.12

  Poly-N-acetyllactosamines (poly-LacNAc, [-3Gal(beta 1-4)GlcNAc(beta 1-](n)) are terminal glycan structures present in glycoproteins and glycolipids. Their biological functions as ligands for galectins and as carriers of glycan epitopes are well documented. In the present paper we have characterized six novel functionalized beta-D-GlcNAc derivatives, including aglyca of varying hydrophobicity and molecular weight, as substrates for recombinant human beta 1,4 galactosyltransferase 1 (beta 4GalT-1). The sugar derivatives carry short or long amino- or azide-terminated linker molecules for further modification or immobilization. The linker chemistry had an impact on enzyme kinetics and enzymatic syntheses of N-acetyllactosamine derivatives (LacNAc, Gal(beta 1-4)GlcNAc(beta 1-R). The combination of beta 4GaIT-1 with bacterial beta 1,3-N-acetylglucosaminyltransferase (beta 3GlcNAc-T) resulted in the preparative syntheses of LacNAc oligomers with up to three LacNAc repeating units. All products were characterized by NMR and MS. The obtained LacNAc glycans were immobilized onto microtiter plates and their efficiency of binding of fungal galectin CGL2 was determined. (C) 2012 Elsevier B.V. All rights reserved.
• Carbohydrate Microarrays for Assaying Galactosyltransferase Activity
  作者：Sungjin Park、Injae Shin

  DOI：10.1021/ol070250l

  日期：2007.4.1

  Carbohydrate microarrays have been used recently for the rapid analysis of glycan-protein or glycan-cell interactions and for the detection of pathogens. As a demonstration of its significance and versatility, the microarray technology has been applied in this effort to assay glycosyltransferase activities. In addition, carbohydrate microarray based methods have been employed to quantitatively determine binding affinities between lectins and carbohydrates.
• Synthesis of N-acetyllactosamine-containing oligosaccharides, galectin ligands
  作者：V. V. Severov、I. M. Belyanchikov、G. V. Pazynina、N. V. Bovin

  DOI：10.1134/s1068162007010141

  日期：2007.2

  The following spacered oligosaccharides were synthesized: GlcNAc beta 1-3Gal beta 1-4GlcNAc beta-sp, GlcNAc beta 1-6Gal beta 1-4GlcNAc beta-sp, GlcNAc beta 1-3(GlcNAc beta 1-6)Gal beta 1-4GlcNAc beta-sp, Gal beta 1-4GlcNAc beta 1-3Gal beta 1-4GlcNAc beta-sp, Gal beta 1-4GlcNAc beta 1-6Gal beta 1-4GlcNAc beta-sp, Gal beta 1-4GlcNAc beta 1-3(Gal beta 1-4GlcNAc beta 1-6)Gal beta 1-4GlcNAc beta-sp, GlcNAc beta 1-3(Gal beta 1-4GlcNAc beta 1-6)Gal beta 1-4GlcNAc beta-sp, and Gal beta 1-4GlcNAc beta 1-3(GlcNAc beta 1-6)Gal beta 1-4GlcNAc beta-sp (sp = O(CH2)(2)NH2). They represent N-acetyllactosamines substituted with N-acetylglycosamine or N-acetyllalctosamine residue at O3, O6, or at both positions of galactose. Glycosylation was achieved by coupling with N-trichloroethoxycarbonyl-protected glucosamine bromide in the presence of silver triflate.