UDP-N-acetyl-6-azido-6-deoxy-glucosamine | 1202854-85-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: UDP-N-acetyl-6-azido-6-deoxy-glucosamine
• 英文别名: uridine 5'-diphospho-2-acetamido-6-azido-2,6-dideoxy-α-D-glucopyranoside；6''-azido-6''-deoxy-UDP-N-acetylglucosamine；UDP-6Az-GlcNAc；UDP-GlcNAc6N3；[(2R,3R,4R,5S,6R)-3-acetamido-6-(azidomethyl)-4,5-dihydroxyoxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate
• CAS: 1202854-85-0
• 化学式: C₁₇H₂₆N₆O₁₆P₂
• 分子量: 632.372
• InChiKey: SVLKKCJMKWWPQY-CFRASDGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  295
• 氢给体数：
  8
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  UDP-N-acetyl-6-azido-6-deoxy-glucosamine 在 palladium on activated charcoal 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 UDP-6-acetoxyacetamido-N-acetyl-glucosamine
  参考文献：
  名称：

  One-pot three-enzyme synthesis of UDP-GlcNAc derivatives

  摘要：

  一种荚膜多糖杆菌N-乙酰葡糖胺1-磷酸尿苷酰转移酶（PmGlmU）被克隆并有效用于与N-乙酰己糖胺1-激酶（NahK_ATCC55813）及无机焦磷酸酶（PmPpA）联合，实现了一锅法三酶合成UDP-GlcNAc衍生物，必要时可进一步进行化学衍生化。

  DOI：

  10.1039/c1cc14034e
• 作为产物：
  描述：

  在 四氮唑 、 sodium azide 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 生成 UDP-N-acetyl-6-azido-6-deoxy-glucosamine
  参考文献：
  名称：

  6″-Azido-6″-deoxy-UDP-N-acetylglucosamine as a glycosyltransferase substrate

  摘要：

  6 ''-Azido-6 ''-deoxy-UDP-N-acetylglucosamine (UDP-6Az-GlcNAc) is a potential alternate substrate for N-acetylglucosaminyltransferases. This compound could be used to generate various glycoconjugates bearing an azide functionality that could in turn be subjected to further modification using Staudinger ligation or Huisgen cycloaddition. UDP-6Az-GlcNAc is synthesized from alpha-benzyl-N-acetylglucosaminoside in seven-steps with an overall yield of 6%. It is demonstrated to serve as a substrate donor for the glycosyl transfer reaction catalyzed by the human UDP-GlcNAc:polypeptidyltransferase (OGT) to the acceptor protein nucleoporin 62 (nup62). (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.090

文献信息

• Donor substrate promiscuity of bacterial β1–3-N-acetylglucosaminyltransferases and acceptor substrate flexibility of β1–4-galactosyltransferases
  作者：Yanhong Li、Mengyang Xue、Xue Sheng、Hai Yu、Jie Zeng、Vireak Thon、Yi Chen、Musleh M. Muthana、Peng G. Wang、Xi Chen

  DOI：10.1016/j.bmc.2016.02.043

  日期：2016.4

  beta4GalTs, donor substrate specificity studies of two bacterial beta3GlcNAcTs from Helicobacter pylori (Hpbeta3GlcNAcT) and Neisseria meningitidis (NmLgtA), respectively, using a library of 39 sugar nucleotides were carried out. The two beta3GlcNAcTs have complementary donor substrate promiscuity and 13 different trisaccharides were produced. They were used to investigate the acceptor substrate specificities

  beta1-3-N-乙酰氨基葡萄糖氨基转移酶（beta3GlcNAcTs）和beta1-4-半乳糖基转移酶（beta4GalTs）已广泛用于酶法合成含N-乙酰乳糖胺（LacNAc）的寡糖和包括聚LacNAc和乳糖（N-新四糖）的糖缀合物LNnT）存在于人类和其他哺乳动物的乳汁中。为了探索可以通过β3GlcNAcT和β4GalT的组合合成的寡糖和衍生物，分别使用39个糖核苷酸库对来自幽门螺杆菌（Hpbeta3GlcNAcT）和脑膜炎奈瑟氏球菌（NmLgtA）的两种细菌β3GlcNAcT的供体底物特异性进行了研究。执行。这两个beta3GlcNAcT具有互补的供体底物混杂，并产生了13种不同的三糖。他们分别用来研究三种脑膜炎奈瑟氏球菌（NmLgtB），幽门螺杆菌（Hpbeta4GalT）和牛（Bbeta4GalT）的beta4GalT的受体底物特异性。13种三糖中有10种被证明是这些beta4
• Chemoenzymatic Synthesis of Unnatural Nucleotide Sugars for Enzymatic Bioorthogonal Labeling
  作者：Liuqing Wen、Madhusudhan Reddy Gadi、Yuan Zheng、Christopher Gibbons、Shukkoor Muhammed Kondengaden、Jiabin Zhang、Peng George Wang

  DOI：10.1021/acscatal.8b02081

  日期：2018.8.3

  advantage of relaxed donor specificity and strict acceptor specificity of glycosyltransferases to label target glycan epitopes with bioorthogonal reactive groups carried by unnatural nucleotide sugars in vitro. The subsequent covalent conjugation by bioorthogonal chemical reactions with either fluorescent or affinity tags allows further visualization, quantification, or enrichment of target glycan epitopes

  近年来，酶促生物正交标记策略的发展为探测结构确定的聚糖表位提供了令人兴奋的可能性。该策略利用放宽的供体特异性和糖基转移酶的严格受体特异性来利用体外由非天然核苷酸糖携带的生物正交反应基团标记目标聚糖表位。随后通过与荧光标记或亲和标记的生物正交化学反应进行的共价缀合，可以使目标聚糖表位进一步可视化，定量或富集。然而，由于非天然核苷酸糖的有限可用性，已经阻碍了酶标记策略的应用和发展。在此处，描述了将化学合成和酶促合成相结合的平台，以方便地制备经各种生物正交反应基团修饰的非天然核苷酸糖。通过该平台，成功合成了25个UDP-GlcNAc和UDP-GalNAc衍生物，其中包括开发最深入的生物正交官能团。此外，还评估了这些化合物在酶促生物正交标记反应中的潜在应用。
• CHEMOENZYMATIC SYNTHESIS OF HEPARIN AND HEPARAN SULFATE ANALOGS
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20140235575A1

  公开（公告）日：2014-08-21

  The present invention provides a one-pot multi-enzyme method for preparing UDP-sugars from simple sugar starting materials. The invention also provides a one-pot multi-enzyme method for preparing oligosaccharides from simple sugar starting materials.

  本发明提供了一种一锅多酶法，用于从简单糖起始材料制备UDP糖。该发明还提供了一种一锅多酶法，用于从简单糖起始材料制备寡糖。
• BISECTING-GLYCAN BRIDGED CONJUGATION FOR PRODUCING GLYCOPROTEIN CONJUGATES
  申请人：[en]MERCK SHARP & DOHME LLC

  公开号：WO2024102603A1

  公开（公告）日：2024-05-16

  A bisecting glycan-bridged conjugation strategy that enables site-specific conjugation of glycoproteins without the need for chemical synthesis of oligosaccharide and amino acid engineering is disclosed. Application of this method is demonstrated by conjugation of human and mouse antibodies with a cytotoxin. This strategy preserves the Fc effector function of the antibodies and provides the ability to remodel glycans to fine-tune the immunogenicity and pharmacokinetic properties of antibody-drug conjugates through glycoengineering.
• One-pot three-enzyme synthesis of UDP-GlcNAc derivatives
  作者：Yi Chen、Vireak Thon、Yanhong Li、Hai Yu、Li Ding、Kam Lau、Jingyao Qu、Liana Hie、Xi Chen

  DOI：10.1039/c1cc14034e

  日期：——

  A Pasteurella multocida N-acetylglucosamine 1-phosphate uridylyltransferase (PmGlmU) was cloned and used efficiently with an N-acetylhexosamine 1-kinase (NahK_ATCC55813) and an inorganic pyrophosphatase (PmPpA) for one-pot three-enzyme synthesis of UDP-GlcNAc derivatives with or without further chemical diversification.

  一种荚膜多糖杆菌N-乙酰葡糖胺1-磷酸尿苷酰转移酶（PmGlmU）被克隆并有效用于与N-乙酰己糖胺1-激酶（NahK_ATCC55813）及无机焦磷酸酶（PmPpA）联合，实现了一锅法三酶合成UDP-GlcNAc衍生物，必要时可进一步进行化学衍生化。