4-azido-4-deoxy-D-glucose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-azido-4-deoxy-D-glucose
• 英文别名: (3R,4S,5S,6S)-5-azido-6-(hydroxymethyl)oxane-2,3,4-triol
• 化学式: C₆H₁₁N₃O₅
• 分子量: 205.17
• InChiKey: UMVGRQGCOVIFLI-GASJEMHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-azido-4-deoxy-D-glucose 在 palladium dihydroxide 氢气 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.75h， 生成 4-amino-1,2-O-isopropylidene-α-D-glucopyranose
  参考文献：
  名称：

  Model for Antibiotic Optimization via Neoglycosylation:  Synthesis of Liponeoglycopeptides Active against VRE

  摘要：

  The neoglycosylation of a methoxyamine-appended vancomycin aglycon with all possible N'-decanoylglucopyranose and N'-biphenoylglucopyranose regioisomers led to the production of a focused set of liponeoglycopeptide variants in good yields and with excellent stereoselectivity. High-throughput antibacterial assays employing a unique set of vancomycin-resistant Enterococci faecalis and Enterococci faecium clinical isolates revealed that the nature and regiochemistry of glycosyl lipidation modulated vancomycin-resistent Enterococci potency. In contrast to prior work with lipoglycopeptides, this study reveals the glucose C3' or C4' as the optimal position for neoglycopeptide lipidation. This purely chemical method for the diversification of the glycolipid portion of lipoglycopeptide antibiotics is simple to perform on a large scale, requires minimal synthetic effort in sugar donor preparation, and provides access to highly active antibiotics that are not easily prepared by other state-of-the-art methods.

  DOI：

  10.1021/ja068602r
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 吡啶 、 sodium azide 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 4-azido-4-deoxy-D-glucose
  参考文献：
  名称：

  Model for Antibiotic Optimization via Neoglycosylation:  Synthesis of Liponeoglycopeptides Active against VRE

  摘要：

  The neoglycosylation of a methoxyamine-appended vancomycin aglycon with all possible N'-decanoylglucopyranose and N'-biphenoylglucopyranose regioisomers led to the production of a focused set of liponeoglycopeptide variants in good yields and with excellent stereoselectivity. High-throughput antibacterial assays employing a unique set of vancomycin-resistant Enterococci faecalis and Enterococci faecium clinical isolates revealed that the nature and regiochemistry of glycosyl lipidation modulated vancomycin-resistent Enterococci potency. In contrast to prior work with lipoglycopeptides, this study reveals the glucose C3' or C4' as the optimal position for neoglycopeptide lipidation. This purely chemical method for the diversification of the glycolipid portion of lipoglycopeptide antibiotics is simple to perform on a large scale, requires minimal synthetic effort in sugar donor preparation, and provides access to highly active antibiotics that are not easily prepared by other state-of-the-art methods.

  DOI：

  10.1021/ja068602r

文献信息

• Synthesis of azido-deoxy and amino-deoxy glycosides and glycosyl fluorides for screening of glycosidase libraries and assembly of substituted glycosides
  作者：Hong-Ming Chen、Stephen G. Withers

  DOI：10.1016/j.carres.2018.07.007

  日期：2018.9

  useful tools in the probing of biological systems as well as in the assembly of libraries of derivatives using click chemistry or simple amine coupling approaches. A collection of methylumbelliferyl glycosides of various azido- and amino-deoxy sugar derivatives of glucose, galactose and xylose was synthesised via azide displacement of the corresponding triflate derivatives and subsequent modification.

  叠氮化物和胺取代的糖在探测生物系统以及使用点击化学或简单的胺偶联方法组装衍生物库中可能是有用的工具。通过叠氮化物置换相应的三氟甲磺酸衍生物并随后进行修饰，合成了葡萄糖，半乳糖和木糖的各种叠氮基和氨基脱氧糖衍生物的甲基伞形糖苷苷。这些化合物将在高通量筛选中用作底物，以鉴定可加工此类修饰糖的糖苷酶。还合成了每种修饰糖的α-糖基氟衍生物，以用作衍生自筛选中鉴定的酶的糖合酶底物。
• Total synthesis of sorbistin A1 and a positional isomer
  作者：Tomoya Ogawa、Kiyoaki Katano、Masanao Matsui

  DOI：10.1016/0040-4020(80)80148-7

  日期：1980.1

  Total synthesis of sorbistin A1 (1) and a positional isomer (7) is described for the first time in a regio- and stereo-controlled manner.

  首次以区域和立体控制的方式描述了山梨素A 1（1）和位置异构体（7）的全合成。
• Assembly of Divalent Ligands and Their Effect on Divalent Binding to <i>Pseudomonas aeruginosa</i> Lectin LecA
  作者：Guangyun Yu、Anna Chiara Vicini、Roland J. Pieters

  DOI：10.1021/acs.joc.8b02727

  日期：2019.3.1

  to optimize dynamics and enhance interactions with the protein. Affinities of the divalent ligands were measured by ITC, and Kd's as low as 12 nM were determined, notably for a compounds with either a rigid (phenyl) or flexible (butyl) unit at the core. Introducing a phenyl aglycon moiety next to the galactoside ligands on both termini did indeed lead to a higher enthalpy of binding, which was more than

  制备二价配体作为有问题的铜绿假单胞菌病原体粘附蛋白的抑制剂。桥接两个结合位点使得能够同时结合两个半乳糖部分，这大大增强了结合。葡萄糖，三唑和芳基的交替基序显示具有刚性，溶解性和易于合成的正确组合。间隔物相对于核心单元以及糖苷配基部分是变化的，以试图优化动力学并增强与蛋白质的相互作用。通过ITC测量二价配体的亲和力，并确定低至12 nM的Kd，特别是对于在核心具有刚性（苯基）或柔性（丁基）单元的化合物。在两个末端的半乳糖苷配体旁边引入苯基糖苷配基部分的确确实导致了更高的结合焓，这被熵成本所补偿。将根据热力学以及对预期和观察到的多价效应的理论计算来讨论结果。
• [EN] SYNTHESIS OF LACTONE DERIVATIVES AND THEIR USE IN THE MODIFICATION OF PROTEINS<br/>[FR] SYNTHÈSE DE DÉRIVÉS DE LACTONE ET LEUR UTILISATION DANS LA MODIFICATION DE PROTÉINES
  申请人：GENIE BIOTECH UK LTD

  公开号：WO2021123229A1

  公开（公告）日：2021-06-24

  Site-specific modifications of proteins are desirable in biotechnological applications such as biopharmaceuticals, immunotherapy, vaccines, and are useful in chemical biology. Gluconoylation is a non-enzymatic, covalent, post-translational modification commonly observed on N-terminal His-Tags bearing proteins. We synthesized glucono-1,5-lactone derivatives, including azido variants for selective acylation. High yield acylation is achieved by simply mixing derivatives with target protein amidst diverse conditions of temperatures, aqueous buffers, excipients, or complex cell lysate.

  蛋白质的位点特异性修饰在生物技术应用中是可取的，例如生物制药、免疫疗法、疫苗，并且在化学生物学中也非常有用。葡萄糖酸化是一种非酶促的共价后翻译修饰，常见于带有N-末端His-标签的蛋白质上。我们合成了葡萄糖酸-1,5-内酯衍生物，包括用于选择性酰化的叠氮化衍生物。只需将衍生物与目标蛋白质混合在不同的温度、水溶液缓冲剂、辅料或复杂的细胞裂解液条件下，即可实现高产酰化。
• Colchicine Glycorandomization Influences Cytotoxicity and Mechanism of Action
  作者：Aqeel Ahmed、Noël R. Peters、Megan K. Fitzgerald、James A. Watson,、F. Michael Hoffmann、Jon S. Thorson

  DOI：10.1021/ja064686s

  日期：2006.11.1

  The reaction of 70 unprotected, diversely functionalized free reducing sugars with methoxyamine-appended colchicine led to the production of a 58-member glycorandomized library. High-throughput cytotoxicity assays revealed glycosylation to modulate specificity and potency. Library members were also identified which, unlike the parent natural product (a destabilizer), stabilized in vitro tubulin polymerization in a manner similar to taxol. This study highlights a simple extension of neoglycorandomization toward amine-bearing scaffolds and the potential benefit of glycosylating nonglycosylated natural products.