1,2,3,4-O-四乙酰基-6-叠氮-6-脱氧-a-D-吡喃葡萄糖 | 51642-43-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 1,2,3,4-O-四乙酰基-6-叠氮-6-脱氧-a-D-吡喃葡萄糖
• 中文别名: 四-O-乙酰基-6-叠氮基-6-脱氧-ALPHA-D-吡喃葡萄糖
• 英文名称: 1,2,3,4-tetra-O-acetyl-6-azido-6-deoxy-α-D-glucopyranose
• 英文别名: 1,2,3,4-tetra-O-acetyl-6-azido-6-deoxy-alpha-D-glucopyranose；[(2R,3R,4S,5R,6R)-4,5,6-triacetyloxy-2-(azidomethyl)oxan-3-yl] acetate
• CAS: 51642-43-4
• 化学式: C₁₄H₁₉N₃O₉
• 分子量: 373.32
• InChiKey: LFQWTDKRDROWBN-RGDJUOJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2,3,4-O-四乙酰基-6-叠氮-6-脱氧-a-D-吡喃葡萄糖 在 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 O-(2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranosyl)trichloroacetimidate
  参考文献：
  名称：

  Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin

  摘要：

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

  DOI：

  10.1021/jo035290r
• 作为产物：
  描述：

  methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 在 吡啶 、 sodium azide 、 硫酸 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,2,3,4-O-四乙酰基-6-叠氮-6-脱氧-a-D-吡喃葡萄糖
  参考文献：
  名称：

  Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin

  摘要：

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

  DOI：

  10.1021/jo035290r

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。
• Synthesis of Bifunctional Azobenzene Glycoconjugates for Cysteine-Based Photosensitive Cross-Linking with Bioactive Peptides
  作者：Anne Müller、Hauke Kobarg、Vijayanand Chandrasekaran、Joana Gronow、Frank D. Sönnichsen、Thisbe K. Lindhorst

  DOI：10.1002/chem.201501571

  日期：2015.9.21

  Azobenzene linker molecules can be utilized to control peptide/protein function when they are ligated to appropriately spaced amino acid side chains of the peptide. This is because the photochemical E/Z isomerization of the azobenzene NN double bond allows to switch peptide conformation between folded and unfolded. In this context, we have introduced carbohydrate‐functionalized azobenzene derivatives

  当偶氮苯连接分子与适当间隔的肽氨基酸侧链连接时，可用于控制肽/蛋白质的功能。这是因为偶氮苯NN双键的光化学E / Z异构化可以在折叠和未折叠之间切换肽构象。在这种情况下，我们引入了碳水化合物官能化的偶氮苯衍生物，以提高偶氮苯肽接头的生物相容性。氯乙酰胺官能化和O合成了烯丙基化的碳水化合物衍生物，并与偶氮苯共轭以实现新的双功能交联剂，以便分别通过亲核取代或巯基反应与半胱氨酸侧链连接。确定了新的接头糖缀合物的光致变色性质，并进行了首次连接反应。
• Composition and methods related to modification of 5-hydroxymethylcytosine (5-hmC)
  申请人：He Chuan

  公开号：US08741567B2

  公开（公告）日：2014-06-03

  The present invention relates generally to the field of molecular biology. More particularly, it concerns methods and compositions for detecting, evaluating, and/or mapping 5-hydroxymethyl-modified cytosine bases within a nucleic acid molecule.

  本发明一般涉及分子生物学领域。更具体地说，涉及检测、评估和/或映射核酸分子中的5-羟甲基修饰的胞嘧啶碱基的方法和组合物。
• [EN] A FUNCTIONALIZED GLYCOLIPID AND AN APPLICATION THEREOF<br/>[FR] GLYCOLIPIDE FONCTIONNALISÉ ET SON UTILISATION
  申请人：UNIV MALAYA

  公开号：WO2020204691A1

  公开（公告）日：2020-10-08

  The present invention discloses a functionalized glycolipid having a formula (I): (I) where Y is selected from a group consisting of O, NH and NAc; wherein A is selected from a group of bi-antennary hydrophobic domain having a formula (II): (II) and mono-antennary hydrophobic domain having a formula (III): (III) wherein B having a formula (IV): (IV). Further, the present invention discloses an application of the functionalized glycolipid having the formula (I) thereof. The functionalized glycolipid is usable with a drug delivery carrier for binding biological recognition domain for the cells specific recognition of the carrier via click chemistry.

  本发明揭示了一种具有公式（I）的功能化糖脂：（I），其中Y选自由O、NH和NAc组成的一组，其中A选自具有公式（II）的双天线疏水区域组和具有公式（III）的单天线疏水区域组，其中B具有公式（IV）。此外，本发明还揭示了该公式（I）的功能化糖脂的应用。该功能化糖脂可与药物输送载体一起使用，通过点击化学与细胞特异性识别载体的生物识别结构结合，以实现对载体的细胞特异性识别。
• Cyclic peptide antifungal agents
  申请人：——

  公开号：US20030125240A1

  公开（公告）日：2003-07-03

  The present invention relates to compounds of formula I: 1 where R 5 is a sugar moiety. The compounds are useful in inhibiting fungal and parasitic activity and infections.

  本发明涉及式I的化合物：1其中R5是糖基团。这些化合物在抑制真菌和寄生虫活性和感染方面非常有用。