1-叠氮-1-脱氧-Β-D-吡喃乳糖苷 | 69266-16-6

• 物质功能分类: 生物化工 - 糖类化合物 - 寡糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-叠氮-1-脱氧-Β-D-吡喃乳糖苷
• 英文名称: β-D-lactosyl azide
• 英文别名: β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl azide；β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl azide；4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl azide；1-azido-1-deoxy-β-D-lactopyranoside；1-Azido-1-deoxy-b-D-lactopyranoside；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-6-azido-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 69266-16-6
• 化学式: C₁₂H₂₁N₃O₁₀
• 分子量: 367.313
• InChiKey: FJOYNMRZUBUGGP-DCSYEGIMSA-N

物化性质

• 熔点：
  120 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  184
• 氢给体数：
  7
• 氢受体数：
  12

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29329990
• 储存条件：
  `-20°C`

反应信息

• 作为反应物：
  描述：

  1-叠氮-1-脱氧-Β-D-吡喃乳糖苷 在 palladium on activated charcoal 氢气 、 三苯基膦 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 54.0h， 生成 1-((2R,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenoxy-tetrahydro-pyran-2-ylmethyl)-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-urea
  参考文献：
  名称：

  Synthesis of Urea-Tethered Neoglycoconjugates and Pseudooligosaccharides in Water

  摘要：

  A novel approach to the synthesis of urea glycosides in aqueous media has been explored. Steyermark's glucopyranosyl oxazolidinone was found to be a good synthon for anchoring glucosyl moieties onto amines and thiols. The present method was successfully applied to establish a new route for the synthesis of urea-tethered neoglycoconjugates and pseudooligosaccharides in water.

  DOI：

  10.1021/ja056253f
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 碘代三甲硅烷 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 1-叠氮-1-脱氧-Β-D-吡喃乳糖苷
  参考文献：
  名称：

  合成吡喃葡萄糖基尿酸叠氮化物的一般方法

  摘要：

  首先将衍生自单糖和二糖的过-O-乙酰化D-甘露聚糖转化为糖基碘，然后与叠氮化物源反应，以在脱乙酰基反应后实现立体选择性合成β-D-糖基叠氮化物。单糖的低温（4摄氏度）TEMPO氧化提供了相应的糖醛酸，其被纯化为游离酸。乳糖基和纤维二糖叠氮化物的氧化导致二酸形成。然而，4'，6'-O-亚苄基保护能够选择性氧化C-6羟基。还制备了2-乙酰胺基-2-脱氧-D-甘露糖基叠氮化物，并将其转化为糖醛酸，从而完成了文库的合成。

  DOI：

  10.1016/s0008-6215(03)00042-9

文献信息

• The search for new amphiphiles: synthesis of a modular, high-throughput library
  作者：George C Feast、Thomas Lepitre、Xavier Mulet、Charlotte E Conn、Oliver E Hutt、G Paul Savage、Calum J Drummond

  DOI：10.3762/bjoc.10.163

  日期：——

  Amphiphilic compounds are used in a variety of applications due to their lyotropic liquid-crystalline phase formation, however only a limited number of compounds, in a potentially limitless field, are currently in use. A library of organic amphiphilic compounds was synthesised consisting of glucose, galactose, lactose, xylose and mannose head groups and double and triple-chain hydrophobic tails. A modular, high-throughput approach was developed, whereby head and tail components were conjugated using the copper-catalysed azide–alkyne cycloaddition (CuAAC) reaction. The tails were synthesised from two core alkyne-tethered intermediates, which were subsequently functionalised with hydrocarbon chains varying in length and degree of unsaturation and branching, while the five sugar head groups were selected with ranging substitution patterns and anomeric linkages. A library of 80 amphiphiles was subsequently produced, using a 24-vial array, with the majority formed in very good to excellent yields. A preliminary assessment of the liquid-crystalline phase behaviour is also presented.

  两亲性化合物因其能在液晶相形成而广泛应用于多种领域，然而在潜在无限的领域中，目前只有有限的化合物在使用。本研究合成了一组有机两亲性化合物库，包括葡萄糖、半乳糖、乳糖、木糖和甘露糖的头部基团以及双链和三链的疏水尾部。采用了一种模块化、高通量的方法，通过铜催化的叠氮化物-炔烃环加成反应（CuAAC）将头部和尾部组件连接起来。尾部是从两个核心炔烃连接的中间体合成的，随后用不同长度、不饱和度和分支度的烃链进行官能化，而五个糖头部基团则选择了不同的取代模式和异头连接方式。随后，使用24孔阵列产生了一个包含80个两亲分子的库，其中大多数形成了非常好的到优秀的产率。本文还初步评估了这些化合物的液晶相行为。
• Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry
  作者：Daniel Fürniss、Timo Mack、Frank Hahn、Sidonie B L Vollrath、Katarzyna Koroniak、Ute Schepers、Stefan Bräse

  DOI：10.3762/bjoc.9.7

  日期：——

  Sugar moieties are present in a wide range of bioactive molecules. Thus, having versatile and fast methods for the decoration of biomimetic molecules with sugars is of fundamental importance. The glycosylation of peptoids and polyamines as examples of such biomimetic molecules is reported here. The method uses Cu-catalyzed azide alkyne cycloaddition to promote the reaction of azidosugars with either polyamines or peptoids. In addition, functionalized nucleic acids were attached to polyamines via the same route. Based on a modular solid-phase synthesis of peralkynylated peptoids with up to six alkyne groups, the latter were modified with azidosugar building blocks by using copper-catalyzed azide alkyne cycloadditions. In addition, the up-scaling of some particular azide-modified sugars is described.

  糖基团存在于各种生物活性分子中。因此，拥有多功能且快速的方法来装饰仿生分子与糖类是至关重要的。本文报道了肽酰胺和多胺的糖基化作为这类仿生分子的示例。该方法利用铜催化的偶联反应促进了偶联糖与多胺或肽酰胺的反应。此外，通过相同途径将功能化核酸连接到多胺上。基于固相合成的含有最多六个炔基团的肽酰胺的模块化方法，后者通过铜催化的偶联反应与偶联糖基块进行修饰。此外，还描述了某些特定的偶联糖修饰的扩大规模过程。
• Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids
  作者：Laiqiang Ying、Jacquelyn Gervay-Hague

  DOI：10.1016/j.carres.2003.10.018

  日期：2004.1

  The synthesis of 10 N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids that are amenable to solid-phase synthesis is described. The general synthetic strategy involves initial incorporation of the protected amine, followed by selective TEMPO oxidation of C-6 hydroxyl groups to give the corresponding Fmoc-protected sugar amino acids. Amine incorporation may be accomplished from aminolysis

  描述了适于固相合成的10种N-（氟-9-基甲氧基羰基）甘露糖基氨基糖醛酸的合成。一般的合成策略包括首先引入受保护的胺，然后对C-6羟基进行TEMPO选择性氧化，得到相应的Fmoc保护的糖氨基酸。胺的掺入可通过游离糖的氨解或糖基叠氮化物的还原来完成。该反应可以以多克级进行，从而提供了访问独特单体单元的途径，以便将来将其并入组合文库合成中。
• Exploration of the Reactivity of Multivalent Electrophiles for Affinity Labeling: Sulfonyl Fluoride as a Highly Efficient and Selective Label
  作者：Nanako Suto、Shione Kamoshita、Shoichi Hosoya、Kaori Sakurai

  DOI：10.1002/anie.202104347

  日期：2021.7.26

  that multivalent arylsulfonyl fluoride probe 4 at 50 nm concentration achieved selective affinity labeling and enrichment of a model protein PNA in cell lysate, which was more effective than photoaffinity probe 1 with arylazide group. Labeling site analysis by LC–MS/MS revealed that the nanoparticle-immobilized arylsulfonyl fluoride group can target multiple amino acid residues around the ligand binding

  在这里，我们探索了一组与金纳米粒子上的碳水化合物配体共官能化的多价亲电试剂的反应性，以实现对目标蛋白质分析的有效亲和标记。评估亲电试剂对三种不同的同源结合蛋白的反应性和选择性，确定芳基磺酰氟是本研究中最有效的蛋白质反应性基团。我们表明，多价芳基磺酰基氟化物探针4在50牛顿米浓度达到在细胞裂解物中的模型蛋白质PNA，比光亲和探针更有效的选择性的亲和标记和富集1带有芳基叠氮基。LC-MS/MS 标记位点分析表明，纳米颗粒固定的芳基磺酰氟基团可以靶向靶蛋白配体结合位点周围的多个氨基酸残基。我们的研究强调了芳基磺酰氟作为高效多价亲和标记的实用性，适用于共价捕获未知目标蛋白。
• Glycosyl-nucleoside fluorinated amphiphiles as components of nanostructured hydrogels
  作者：Guilhem Godeau、Christophe Brun、Hélène Arnion、Cathy Staedel、Philippe Barthélémy

  DOI：10.1016/j.tetlet.2009.12.042

  日期：2010.2

  The synthesis of two novel glycosyl-nucleoside fluorinated amphiphiles (GNFs) derived from the 2H,2H,3H,3H-perfluoro-undecanoyl hydrophobic chain is described. The GNF amphiphiles, which feature either β-d-glucopyranosyl or β-d-lactopyranosyl moieties linked to a thymine base via a 1,2,3 triazole linker, were prepared using a ‘double click’ chemistry route. Surface tension measurements, gelation properties

  描述了衍生自2 H，2 H，3 H，3 H-全氟十一碳酰基疏水链的两个新型糖基-核苷氟化两亲物（GNF）的合成。使用“双击”化学路线制备了以β- d-吡喃葡萄糖基或β- d-戊吡喃糖基部分通过1,2,3三唑接头与胸腺嘧啶碱基连接的GNF两亲物。表面张力测量，胶凝性质和TEM研究表明，GNF自发组装成超分子结构。类似于其碳氢化合物类似物（GNL），GNF在水中具有独特的胶凝特性。对于β-d-吡喃葡萄糖基衍生物。细胞活力研究表明，碳氟化合物GNF 5对人细胞（Huh7）无毒，而碳氢化合物类似物GNL在100μm以上有毒。