4-pentenyl 2-acetamido-2-deoxy-α-D-galactopyranoside | 851871-25-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-pentenyl 2-acetamido-2-deoxy-α-D-galactopyranoside
• 英文别名: N-[(2S,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-pent-4-enoxyoxan-3-yl]acetamide
• CAS: 851871-25-5
• 化学式: C₁₃H₂₃NO₆
• 分子量: 289.329
• InChiKey: UMVRPAGHMFPQMZ-LBELIVKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-pentenyl 2-acetamido-2-deoxy-α-D-galactopyranoside 、 硫代乙酸 在 偶氮二异丁腈 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到5-thioacetylpentyl 2-acetamido-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Preparation of multifunctional glyconanoparticles as a platform for potential carbohydrate-based anticancer vaccines

  摘要：

  A novel platform for anticancer vaccines has been prepared using glyconanotechnology recently developed in our laboratory. Ten different multifunctional gold glyconanoparticles incorporating sialylTn and Lewis(y) antigens, T-cell helper peptides (TT) and glucose in well defined average proportions and with differing density have been synthesised in one step and characterised using NMR and TEM. Size and nature of the linker were crucial to control kinetics of S-Au bond formation and to achieve the desired ligand ratio on the gold clusters. The technology presented here opens the way for tailoring polyvalent anticancer vaccines candidates and drug delivery carriers with defined average chemical composition. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.11.018
• 作为产物：
  描述：

  4-pentenyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以100%的产率得到4-pentenyl 2-acetamido-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Preparation of multifunctional glyconanoparticles as a platform for potential carbohydrate-based anticancer vaccines

  摘要：

  A novel platform for anticancer vaccines has been prepared using glyconanotechnology recently developed in our laboratory. Ten different multifunctional gold glyconanoparticles incorporating sialylTn and Lewis(y) antigens, T-cell helper peptides (TT) and glucose in well defined average proportions and with differing density have been synthesised in one step and characterised using NMR and TEM. Size and nature of the linker were crucial to control kinetics of S-Au bond formation and to achieve the desired ligand ratio on the gold clusters. The technology presented here opens the way for tailoring polyvalent anticancer vaccines candidates and drug delivery carriers with defined average chemical composition. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.11.018

文献信息

• Inhibition of Mitosis by Glycopeptide Dendrimer Conjugates of Colchicine
  作者：David Lagnoux、Tamis Darbre、M. Lienhard Schmitz、Jean-Louis Reymond

  DOI：10.1002/chem.200401294

  日期：2005.6.20

  devices for colchicine. Colchicine was attached to the dendrimers at the cysteine thiol group through a disulfide or thioether linkage. The biological activities of the glycopeptide dendrimer conjugates were evaluated in HeLa tumor cells and non-transformed mouse embryonic fibroblasts (MEFs). The concentrations of glycopeptide dendrimer drug conjugates required to achieve inhibition of cell proliferation

  已经制备了糖肽树状聚合物，其表面上带有四个或八个相同的糖苷部分（β-葡萄糖，α-半乳糖，α-N-乙酰基半乳糖或乳糖），分支内的天然氨基酸（Ser，Thr，His，Asp ，Glu，Leu，Val，Phe），2,3-二氨基丙酸作为分支单元，并在核心保留一个半胱氨酸残基。这些树状聚合物已被用作秋水仙碱的药物递送装置。秋水仙碱通过二硫键或硫醚键连接到半胱氨酸硫醇基团的树枝状聚合物上。在HeLa肿瘤细胞和未转化的小鼠胚胎成纤维细胞（MEF）中评估了糖肽树状聚合物结合物的生物学活性。发现通过干扰微管蛋白系统达到抑制细胞增殖所需的糖肽树状聚合物结合物的浓度比秋水仙碱浓度要高（IC50> 1 microM）。另一方面，糖肽树状大分子缀合物抑制HeLa细胞的增殖比MEF的增殖有效20到100倍。相比之下，非糖基化树状大分子和秋水仙碱本身对HeLa细胞的选择性是10倍或更低。