2-azidoethyl 2-N-acetyl-2-deoxy-α-D-galactopyranoside | 195384-42-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidoethyl 2-N-acetyl-2-deoxy-α-D-galactopyranoside
• 英文别名: 2-azidoethyl 2-acetamido-2-deoxy-α-D-galactopyranoside；1-O-(2-Azidoethoxy)-2-acetamido-2deoxy-alpha-D-galactopyranoside；N-[(2S,3R,4R,5R,6R)-2-(2-azidoethoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 195384-42-0
• 化学式: C₁₀H₁₈N₄O₆
• 分子量: 290.276
• InChiKey: DHQJPCIPZHPDSL-SPFKKGSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-azidoethyl 2-N-acetyl-2-deoxy-α-D-galactopyranoside 在 palladium on activated charcoal 吡啶 、 氢气 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 70.0h， 生成 (2R,2'R,3R,3'R,4R,4'R,5R,5'R,6S,6'S)-((((6,6'-(([2,2'-bipyridine]-4,4'-dicarbonyl)bis(azanediyl))bis(hexanoyl))bis(azanediyl))bis(ethane-2,1-diyl))bis(oxy))bis(5-acetamido-2-(acetoxymethyl)tetrahydro-2H-pyran-6,3,4-triyl) tetraacetate
  参考文献：
  名称：

  Cu(II)-Self-assembling bipyridyl-glycoclusters and dendrimers bearing the Tn-antigen cancer marker: syntheses and lectin binding properties

  摘要：

  Using the carbohydrate cancer marker, T-N-antigen (alpha-GalNAc-OR), covalently linked to a bipyridine core, square planar complexes were formed by self-assembly upon simple addition of Cu(11) sulfate. The required alpha-D-GalNAc-OR building block was constructed from 2-azidoethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside (GlcNAc) by epimerization at C-4 of a suitably protected derivative followed by conventional modifications to provide 2-aminoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-galactopyranoside. The 2-aminoethyl aglycone was further elongated into a key monomer having an aminocaproic acid spacer together with their corresponding dimers using a double N-alkylation strategy of their N-bromoacetyl derivatives using mono-Boc-1,4-diaminobutane, respectively. The building blocks containing the bipyridyl dimers, having either a short or a long spacer arm, together with the tetramer built from the short spacer derivative were prepared in a convergent manner using 2,2'-bipyridine-4,4'-dicarboxylic acid chloride and the aminated sugar derivatives, respectively. Copper(II)-nucleated GalNAc derivatives containing four and eight residues were obtained from an aqueous solution of the bipyridyl derivatives. The relative inhibitory potencies of these glycodendrimers were evaluated against monomeric allyl alpha-D-GalNAc using a solid-phase competition assay with asialoglycophorin and horseradish peroxidase-labeled lectin Vicia villosa. The di- and tetra-valent bipyridyl clusters showed up to 87-fold increased inhibitory properties (IC50 7.14, 1.82, 4.09 muM, respectively) when compared to the monomer (IC50 158.3 muM) while the Cu(II)-complexes showed up to a 259-fold increase potencies (IC50 0.61 muM) with the octamer showing the highest affinity. However, when expressed on a per-saccharide basis, the tetramer Cu(II) nucleated derivative, possessing the longest inter-sugar distances showed the highest affinity (IC50 0.63 muM). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00438-1
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-D-吡喃半乳糖 在 sodium azide 、 乙酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-azidoethyl 2-N-acetyl-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  鼠李糖修饰的牛血清白蛋白作为载体蛋白可促进针对sTn抗原的免疫反应

  摘要：

  将鼠李糖和sTn抗原共轭于牛血清白蛋白（BSA）（一种免疫原性较弱的载体蛋白），以开发癌症疫苗。Rha特异性抗体的参与可显着增强针对sTn的免疫反应，从而增强抗原摄取。

  DOI：

  10.1039/d0cc05263a

文献信息

• 一种单磷酸类酯A缀合Tn抗肿瘤疫苗及其应用
  申请人：广州中医药大学（广州中医药研究院）

  公开号：CN110075291B

  公开（公告）日：2023-01-06

  本发明提供了一种单磷酸类酯A缀合Tn抗肿瘤疫苗，其是通式为(I)的化合物：Y‑L‑X(I)。本发明是以第二代全新结构的TLR4配体式I的化合物来代替MPLA与具有临床开发潜力的式Ⅱ化合物(Tn)偶联获得具有结构明确、能产生更强抗肿瘤作用的两组分疫苗，具有较好的抗肿瘤应用前景。
• A One-Step Synthesis of Azide-Tagged Carbohydrates: Versatile ­Intermediates for Glycotechnology
  作者：Lara Mahal、Aditya Sanki

  DOI：10.1055/s-2006-926264

  日期：——

  Herein we describe a simple and practical methodology for accessing both the α-anomers (d-mannose, N-acetyl-d-glucosamine, N-acetyl-d-galactosamine, d-lactose) and α- and β-anomers (d-glucose, d-galactose, l-fucose) of 2′-azidoethyl and azidotriethylene glycol glycosides using free sugars and Dowex 50 (resin) as an efficient catalyst. These azidoalkyl glycosides are increasingly useful synthetic intermediates for glycotechnology.

  本文描述了一种简单实用的方法，能够获取2′-氮杂乙基和氮杂三乙烯二醇糖苷的α-异构体（d-甘露糖、N-乙酰-d-葡萄糖胺、N-乙酰-d-半乳糖胺、d-乳糖）以及α-和β-异构体（d-葡萄糖、d-半乳糖、l-岩藻糖），采用游离糖和Dowex 50（树脂）作为高效催化剂。这些氮杂烷基糖苷在糖科技中越来越成为有用的合成中间体。
• Full synthesis and bioactivity evaluation of Tn-RC-529 derivative conjugates as self-adjuvanting cancer vaccines
  作者：Lingqiang Gao、Qinghai Lian、Leilei Ma、Shiwei Su、Menglan Yang、Yuan Fang、Zhongqiu Liu、Xiang Luo、Guochao Liao

  DOI：10.1016/j.cclet.2021.03.046

  日期：2021.10

  and efficient strategy was established for the construction of RC-529 and its derivatives. Four conjugates of RC-529 derivatives with Tn antigen were synthesized and all elicited strong and T cell-dependent immune responses in mice without requiring external adjuvants. In addition, all antisera induced by these conjugates could specifically recognize, bind to and kill Tn-overexpressing cancer cells

  为构建RC-529及其衍生物建立了一种简便有效的策略。合成了四种RC-529衍生物与Tn抗原的结合物，它们均在小鼠中引起强力和T细胞依赖性免疫应答，而无需外部佐剂。此外，这些结合物诱导的所有抗血清都可以特异性识别，结合并杀死过表达Tn的癌细胞。因此，RC-529有望成为开发具有自我佐剂特性的新型疫苗载体以治疗癌症的有用平台。此外，初步的结构-活性关系分析为进一步优化RC-529和进一步研究RC-529提供了令人信服的支持。
• 一种含有单磷酸化的脂质A与糖抗原的缀合物及其制备方法和应用
  申请人：广州中医药大学（广州中医药研究院）

  公开号：CN111588847B

  公开（公告）日：2023-05-26

  本发明涉及一种含有单磷酸化的脂质A与糖抗原的缀合物及其制备方法和应用，属于抗肿瘤糖疫苗研制技术领域。本发明提供的一种含有单磷酸化的脂质A与糖抗原的缀合物，所述单磷酸化的脂质A与糖抗原的缀合物为通式为(Ⅰ)的化合物或其可药用盐。单磷酸化的脂质A能提高Tn糖抗原的免疫原性，将Tn糖抗原提呈到相应的免疫细胞，产生具有更高滴度的针对肿瘤糖抗原Tn特异性的免疫反应，因此该缀合物，作为全合成的糖抗原疫苗，有望成为新一代的抗肿瘤药物。
• Synthesis of a Lewis b hexasaccharide thioglycoside donor and its use towards an extended mucin core Tn heptasaccharide structure and a photoreactive biotinylated serine linked hexasaccharide
  作者：Martin Hollinger、Filippo Bonaccorsi、Aisling Ní Cheallaigh、Stefan Oscarson

  DOI：10.1039/d2ob00477a

  日期：——

  Investigation into Heliobacter pylori binding to Lewis b (Leb) antigens through the blood group antigen binding adhesion protein (BabA) requires structurally well-defined tools. A Leb hexasaccharide thioglycoside donor was chemically prepared through a linear approach starting from D-lactose. This donor can be used to attach reducing end linkers providing a range of options for conjugation techniques

  研究幽门螺杆菌通过血型抗原结合粘附蛋白 (BabA)与 Lewis b (Le b ) 抗原结合需要结构明确的工具。Le b六糖硫糖苷供体通过从D-乳糖开始的线性方法化学制备。该供体可用于连接还原末端接头，为缀合技术提供一系列选择，或进一步扩展寡糖结构。为了评估其作为供体的效率，将其与 6-OH GalNAc 受体偶联，以 84% 的产率产生扩展的含有 Le b的 Tn 粘蛋白核心结构，并与L-丝氨酸，产率为 72%。后一种化合物随后用光不稳定的二氮丙啶接头和生物素进行功能化，形成了一种适用于凝集素标记相互作用研究的 Le b六糖结构-功能工具。该供体为 Le b结构的共轭开辟了广泛的可能性，以产生各种化学生物学工具来帮助研究这些相互作用。