5,11,17,23-tetrakis[N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-thioureido]-25,26,27,28-tetrapropoxycalix[4]arene | 803687-45-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,11,17,23-tetrakis[N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-thioureido]-25,26,27,28-tetrapropoxycalix[4]arene
• 英文别名: 5,11,17,23-tetrakis[(2-acetamido-2-deoxy-β-D-glucopyranosyl)thioureido]-25,26,27,28-tetrapropoxycalix[4]arene；N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[11,17,23-tris[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]carbamothioylamino]-25,26,27,28-tetrapropoxy-5-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]carbamothioylamino]oxan-3-yl]acetamide
• CAS: 803687-45-8
• 化学式: C₇₆H₁₀₈N₁₂O₂₄S₄
• 分子量: 1702.02
• InChiKey: SKTKPPUNHNLUDF-CBRRUECVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  116
• 可旋转键数：
  28
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  658
• 氢给体数：
  24
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  uridine 5'-diphosphogalactose disodium salt 、 5,11,17,23-tetrakis[N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-thioureido]-25,26,27,28-tetrapropoxycalix[4]arene 在 β-1,4-galactosyltransferase 、 manganese(ll) chloride 、 alkaline phosphatase 作用下， 以 aq. buffer 为溶剂， 反应 48.0h， 以100%的产率得到5,11,17,23-tetrakis[(β-D-galactopyranosyl-(1,4)-2-acetamido-2-deoxy-β-D-glucopyrano syl)thioureido]-25,26,27,28-tetrapropoxycalix[4]arene
  参考文献：
  名称：

  杯[4]芳烃的化学酶法完全四糖基化

  摘要：

  聚糖基化的杯芳烃是凝集素的有效且选择性的多价配体。然而，这些大环骨架的化学修饰越来越复杂，其糖类的高度复杂化阻碍了这种复杂性。常规方法的替代方法是简单糖簇呈递的聚糖的酶促多样化。在这项工作中，我们提出了一种高效率的化学-酶促方法来四Ñ乙酰基lactosaminylcalix [4]芳烃通过人β-1,4-半乳糖基转移酶催化的糖链延伸。这表明尽管空间密集，拥挤者也可以通过酶促糖基转移来彻底处理杯芳烃，这为基于这些具有复杂支链聚糖的大环骨架的多价配体的设计和实现铺平了道路。

  DOI：

  10.1039/c7ob02448g
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.5h， 以0.36 g的产率得到5,11,17,23-tetrakis[N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-thioureido]-25,26,27,28-tetrapropoxycalix[4]arene
  参考文献：
  名称：

  杯[4]芳烃的化学酶法完全四糖基化

  摘要：

  聚糖基化的杯芳烃是凝集素的有效且选择性的多价配体。然而，这些大环骨架的化学修饰越来越复杂，其糖类的高度复杂化阻碍了这种复杂性。常规方法的替代方法是简单糖簇呈递的聚糖的酶促多样化。在这项工作中，我们提出了一种高效率的化学-酶促方法来四Ñ乙酰基lactosaminylcalix [4]芳烃通过人β-1,4-半乳糖基转移酶催化的糖链延伸。这表明尽管空间密集，拥挤者也可以通过酶促糖基转移来彻底处理杯芳烃，这为基于这些具有复杂支链聚糖的大环骨架的多价配体的设计和实现铺平了道路。

  DOI：

  10.1039/c7ob02448g

文献信息

• Synthesis and Lectin Binding Ability of Glycosamino Acid−Calixarenes Exposing GlcNAc Clusters
  作者：Grazia M. L. Consoli、Francesca Cunsolo、Corrada Geraci、Valentina Sgarlata

  DOI：10.1021/ol0485767

  日期：2004.11.1

  Novel calix[4 or 8]arene-based glycoconjugates exposing terminal N-acetyl-D-glucosamine clusters have been synthesized using amino acid-calixarenes as building blocks. The obtained glycosamino acid-calixarenes 9b-14b have lectin-binding ability and amplified inhibitory effects on erythrocyte agglutination induced by wheat germ (Triticum vulgaris) agglutinin (WGA). The inhibitory ability is dependent on the presence of the spacer and on the shape and rigidity of the calixarene skeleton.
• RETRACTED: N-Acetyl-d-glucosamine substituted calix[4]arenes as stimulators of NK cell-mediated antitumor immune response
  作者：Karel Křenek、Markéta Kuldová、Katarína Hulíková、Ivan Stibor、Pavel Lhoták、Miroslav Dudič、Jan Budka、Helena Pelantová、Karel Bezouška、Anna Fišerová、Vladimír Křen

  DOI：10.1016/j.carres.2007.04.026

  日期：2007.9

  A series of calixarenes substituted with 2-acetamido-2-deoxy-beta-D-glucopyranose linked by a thiourea spacer was prepared and tested for binding activity to heterogeneously expressed activation receptors of the rat natural killer cells NKR-Pl, and the receptor CD69 (human NK cells, macrophages). In the case of NKR-Pl, the binding affinity of beta-D-GlcNAc-substituted calixarenes carrying two or four sugar units was in a good agreement with the inhibitory potencies of the linear chitooligomers (chitobiose to chitotetraose) reported previously. The influence of GlcNAc substitution of the calixarene skeleton on binding affinity for CD69 receptor was more profound and the 5,11,17,23-tetrakis[N-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-thioureido]-25,26,27,28-tetrapropoxycalix[4]arene (cone) (1) proved to be the best CD69 ligand identified to date. Lower GlcNAc substitution led to dramatic decrease of the binding activity (by about 1.5 order of magnitude per one GlcNAc unit). The immuno stimulating activity results with the newly synthesized GlcNAc tetramers on calixarene scaffolds exhibited stimulation of natural cytotoxicity of human PBMC in concentrations 10(-4) and 10(-8) M. These calix-sugar compounds were superior to the previously tested PAMAM-GlcNAc(8) 5. (c) 2007 Elsevier Ltd. All rights reserved.
• Complete tetraglycosylation of a calix[4]arene by a chemo-enzymatic approach
  作者：Silvia Bernardi、Dong Yi、Ning He、Alessandro Casnati、Wolf-Dieter Fessner、Francesco Sansone

  DOI：10.1039/c7ob02448g

  日期：——

  complexity is hampered by the highly complex chemistry of carbohydrates. An alternative to the conventional approach is the enzymatic diversification of simple glycocluster-presented glycans. In this work, we present a highly efficient chemo-enzymatic approach to tetra-N-acetyl-lactosaminylcalix[4]arene via glycan extension catalyzed by a human β-1,4-galactosyltransferase. This demonstrates that calixarenes

  聚糖基化的杯芳烃是凝集素的有效且选择性的多价配体。然而，这些大环骨架的化学修饰越来越复杂，其糖类的高度复杂化阻碍了这种复杂性。常规方法的替代方法是简单糖簇呈递的聚糖的酶促多样化。在这项工作中，我们提出了一种高效率的化学-酶促方法来四Ñ乙酰基lactosaminylcalix [4]芳烃通过人β-1,4-半乳糖基转移酶催化的糖链延伸。这表明尽管空间密集，拥挤者也可以通过酶促糖基转移来彻底处理杯芳烃，这为基于这些具有复杂支链聚糖的大环骨架的多价配体的设计和实现铺平了道路。