triethylammonium 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose-1-yl phosphate | 139883-90-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: triethylammonium 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose-1-yl phosphate
• 英文别名: 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose-1-phosphate triethylamine salt；2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucosyl-1-phosphate triethylammonium salt；2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose 1-phosphate monotriethylammonium salt；3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-glucopyranosyl dihydrogen monophosphate mono(triethylammonium)salt；peracetyl GlcNAc monophosphate mono(triethylammonium) salt；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-phosphonooxyoxan-2-yl]methyl acetate;N,N-diethylethanamine
• CAS: 139883-90-2
• 化学式: C₆H₁₅N*C₁₄H₂₂NO₁₂P
• 分子量: 528.494
• InChiKey: MGLRGHKVJDCHKX-XAWYEFCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  187
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  triethylammonium 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose-1-yl phosphate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以94%的产率得到N-acetyl-alpha-d-glucosamine 1-phosphate disodium salt
  参考文献：
  名称：

  用于研究多羟基连接寡糖二磷酸酶（DLODP）的化学工具的合成和生物学评估

  摘要：

  合成了基于香茅烷基和茄基的多羟基连接的寡糖（DLO）类似物，并与十一碳烯基化合物一起测试了它们通过哺乳动物肝脏DLO二磷酸酶活性抑制[ 3 H] OSP从[ 3 H] DLO释放的能力。茄尼基（C45）和十一碳烯基（C55）化合物的效价比其基于香茅醇（C10）的同类化合物强50-500倍，这表明烷基链长对活性至关重要。香茅基系列中化合物的相对效力不同于茄基系列，其中香茅基二磷酸的效力分别是香茅基-PP-Glc N Ac 2和香茅基-PP-Glc N Ac 2倍和3倍；而茄基-PP-GlcN Ac和茄基-PP-Glc N Ac 2的效力分别比茄基二磷酸酯高4倍和8倍。在抑制DLODP分析时，十一碳烯基-PP-Glc N Ac和细菌脂质II的效力比十一碳烯基二磷酸高8倍。因此，至少对于疏水性更高的化合物而言，二磷酸二酯比二磷酸单酯是DLODP分析更有效的抑制剂。这些结果表明，DLO而不是二磷酸

  DOI：

  10.1016/j.ejmech.2016.10.013
• 作为产物：
  描述：

  2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)[1,2-d]-oxazoline 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 28.0h， 生成 triethylammonium 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose-1-yl phosphate
  参考文献：
  名称：

  [EN] N-GLYCOSYLATION OF PEPTIDES AND PROTEINS
  [FR] N-GLYCOSYLATION DE PEPTIDES ET DE PROTÉINES

  摘要：

  一种通过蛋白质或肽的N-糖基化制备糖蛋白的方法，所述蛋白质或肽包括序列D/E-X-N-X-S/T，其中每个X相同或不同，是任何天然氨基酸，但不包括脯氨酸，该方法包括将蛋白质或肽与式(I)的聚异戊二烯基焦磷酸盐或其盐在PglB的存在下反应，以产生包含与序列D/E-X-N-X-S/T中的天冬氨酸连接的糖蛋白。还提供了作为生物催化过程中底物使用的聚异戊二烯基焦磷酸盐，以及某些糖蛋白。

  公开号：

  WO2015056011A1

文献信息

• A Terpyridine Zinc Complex for Selective Detection of Lipid Pyrophosphates: A Model System for Monitoring Bacterial O- and N-Transglycosylations
  作者：Tse-Wei Hsu、Hsin-Chuan Hsu、Hsin-Yu Chan、Jim-Min Fang

  DOI：10.1021/acs.joc.0c01252

  日期：2020.10.2

  To develop an effective method for probing O- and N-glycosyltransfer reactions that are accompanied by the release of undecaprenyl pyrophosphate, solanesyl pyrophosphate (SPP) is used as a surrogate to bind a terpyridine zinc complex (Tpy-Zn), forming a fluorescent [Tpy-Zn]-SPP complex (Kass 106,000 M–1 in EtOH-CHCl3) with 5.8 μM LOD in HEPES buffer (10 mM, pH 7.4) containing 10 mM CaCl2 and 0.08%

  为了开发一种有效的方法来探测伴有十一碳烯基焦磷酸盐释放的O-和N-糖基转移反应，使用茄基焦磷酸盐（SPP）作为替代物来结合一个联吡啶锌配合物（Tpy-Zn），形成一种荧光[ Tpy-Zn] -SPP络合物（EtOH-CHCl 3中的K驴106,000 M –1），在含有10 mM CaCl 2和0.08％癸基PEG的HEPES缓冲液（10 mM，pH 7.4）中具有5.8μMLOD。脂质II聚合的生物测定条件。
• Rationally Designed Short Polyisoprenol-Linked PglB Substrates for Engineered Polypeptide and Protein N-Glycosylation
  作者：Feng Liu、Balakumar Vijayakrishnan、Amirreza Faridmoayer、Thomas A. Taylor、Thomas B. Parsons、Gonçalo J.L. Bernardes、Michael Kowarik、Benjamin G. Davis

  DOI：10.1021/ja409409h

  日期：2014.1.15

  The lipid carrier specificity of the protein N-glycosylation enzyme C. jejuni PglB was tested using a logical, synthetic array of natural and unnatural C10, C20, C30, and C40 polyisoprenol sugar pyrophosphates, including those bearing repeating cis-prenyl units. Unusual, short, synthetically accessible C20 prenols (nerylnerol 1d and geranylnerol 1e) were shown to be effective lipid carriers for PglB

  使用天然和非天然 C10、C20、C30 和 C40 聚异戊二烯醇糖焦磷酸的合乎逻辑的合成阵列测试了蛋白质 N-糖基化酶空肠弯曲菌 PglB 的脂质载体特异性，包括带有重复顺式-异戊二烯基单元的那些。不寻常的、短的、可合成的 C20 异戊烯醇（橙花醇 1d 和香叶橙花醇 1e）被证明是 PglB 糖底物的有效脂质载体。PglB 的动力学分析揭示了明确的 K(M)-仅调制与脂质链长度，从而暗示在适当浓度下成功的体外应用。这通过优化、有效的体外合成得到证实，允许 >90% 的 Asn 连接的 β-N-GlcNAc 化肽和蛋白质。这揭示了一个简单的，
• Design, synthesis and biological evaluation of carbohydrate-functionalized cyclodextrins and liposomes for hepatocyte-specific targeting
  作者：Gonçalo J. L. Bernardes、Raghavendra Kikkeri、Maha Maglinao、Paola Laurino、Mayeul Collot、Sung You Hong、Bernd Lepenies、Peter H. Seeberger

  DOI：10.1039/c0ob00372g

  日期：——

  Targeting glycan-binding receptors is an attractive strategy for cell-specific drug and gene delivery. The C-type lectin asialoglycoprotein receptor (ASGPR) is particularly suitable for liver-specific delivery due to its exclusive expression by parenchymal hepatocytes. In this study, we designed and developed an efficient synthesis of carbohydrate-functionalized β-cyclodextrins (βCDs) and liposomes for hepatocyte-specific delivery. For targeting of ASGPR, rhodamine B-loaded βCDs were functionalized with glycodendrimers. Liposomes were equipped with synthetic glycolipids containing a terminal D-GalNAc residue to mediate binding to ASGPR. Uptake studies in the human hepatocellular carcinoma cell line HepG2 demonstrated that βCDs and liposomes displaying terminal D-Gal/D-GalNAc residues were preferentially endocytosed. In contrast, uptake of βCDs and liposomes with terminal D-Man or D-GlcNAc residues was markedly reduced. The D-Gal/D-GalNAc-functionalized βCDs and liposomes presented here enable hepatocyte-specific targeting. Gal-functionalized βCDs are efficient molecular carriers to deliver doxorubicin in vitro into hepatocytes and induce apoptosis.

  针对糖结合受体的策略在细胞特异性药物和基因传递中具有吸引力。C型凝集素脱唾液酸糖蛋白受体（ASGPR）由于其仅由实质性肝细胞表达，特别适合于肝脏特异性传递。在本研究中，我们设计并开发了一种高效的碳水化合物功能化β-环糊精（βCDs）和脂质体的合成方法，用于肝细胞特异性传递。为了针对ASGPR进行靶向，罗丹明B负载的βCDs通过糖树枝状聚合物进行功能化。脂质体配备含有末端D-GalNAc残基的合成糖脂，以介导与ASGPR的结合。在人肝细胞癌细胞系HepG2中的摄取研究表明，显示末端D-Gal/D-GalNAc残基的βCDs和脂质体优先被内吞。相比之下，具有末端D-Man或D-GlcNAc残基的βCDs和脂质体的摄取明显减少。这里展示的D-Gal/D-GalNAc功能化的βCDs和脂质体实现了肝细胞特异性靶向。Gal功能化的βCDs是有效的分子载体，能够在体外将多柔比星传递到肝细胞并诱导凋亡。
• Reliable Synthesis of Various Nucleoside Diphosphate Glycopyranoses
  作者：Saskia Wolf、Tanja Zismann、Nathalie Lunau、Chris Meier

  DOI：10.1002/chem.200900572

  日期：2009.8.3

  A reliable and high yielding synthetic pathway for the synthesis of the biologically highly important class of nucleoside diphosphate sugars (NDP‐sugars) was developed by using various cycloSal‐nucleotides 1 and 9 as active ester building blocks. The reaction with anomerically pure pyranosyl‐1‐phosphates 2 led to the target NDP‐sugars 20–45 in a nucleophilic displacement reaction, which cleaves the

  通过使用各种环Sal-核苷酸1和9作为活性酯结构单元，开发了一种可靠且高产的合成途径，用于合成生物学上非常重要的一类核苷二磷酸糖（NDP-糖）。与端基异构体纯的吡喃糖基-1-磷酸的反应2导致目标NDP-糖20 - 45在亲核取代反应，其切割的环在端基异构体纯的形式萨尔部分。作为核苷，可使用胞苷，尿苷，胸苷，腺苷，2'-脱氧鸟苷和2'，3'-二脱氧-2'，3'-二脱氢胸苷，而D-葡萄糖，D的磷酸盐引入了半乳糖，D-甘露糖，D - N-氨基葡萄糖，D - N-半乳糖胺，D-岩藻糖，L-岩藻糖以及6-脱氧-D-果糖。
• Diphosphate formation using cyanuric chloride or triisopropylbenzenesulfonyl chloride as the activating agents
  作者：Teng-Chi Lin、Jim-Min Fang

  DOI：10.1016/j.tetlet.2011.01.034

  日期：2011.4

  By using cyanuric chloride or 2,4,6-triisopropylbenzenesulfonyl chloride (TIPSCl) as the condensing agent and magnesium bromide as the promoter, the phosphate cross-coupling reactions are effectively carried out to give lipid-saccharide and pyrrolidine-guanosine diphosphates. Under optimized conditions, the TIPSCl-facilitated cross-coupling reactions complete in a short reaction time (similar to 5 h) without the complication of possible self-coupling reactions. (c) 2011 Elsevier Ltd. All rights reserved.