3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride | 130539-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride
• 英文别名: 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucosyl fluoride；3,4,6-Tri-o-acetyl-2-deoxy-2-phthalimido-b-d-glucopyranosyl fluoride；[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-fluorooxan-2-yl]methyl acetate
• CAS: 130539-42-3
• 化学式: C₂₀H₂₀FNO₉
• 分子量: 437.379
• InChiKey: YRVBOYANNCZRHU-DUQPFJRNSA-N

物化性质

• 熔点：
  115 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  534.3±50.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis and Use of Mechanism-Based Protein-Profiling Probes for Retaining β-d-Glucosaminidases Facilitate Identification of Pseudomonas aeruginosa NagZ

  摘要：

  The NagZ class of retaining exo-glucosaminidases play a critical role in pepticloglycan recycling in Gram-negative bacteria and the induction of resistance to beta-lactams. Here we describe the concise synthesis of 2-azidoacetyl-2-deoxy-5-fluoro-beta-D-glucopyranosyl fluoride as an activity-based proteomics probe for profiling these exo-glycosidases. This active-site directed reagent covalently inactivates this class of retaining N-acetylglucosaminidases with exquisite selectivity by stabilizing the glycosyl-enzyme intermediate. Inactivated Vibrio cholerae NagZ can be elaborated with biotin or a FLAG-peptide epitope using the Staudinger ligation or the Sharpless-Meldal click reaction and detected at nanogram levels. This ABPP enabled the profiling of the Pseudomonas aeruginosa proteome and identification at endogenous levels of a tagged protein with properties consistent with those of PA3005. Cloning of the gene encoding this hypothetical protein and biochemical characterization enabled unambiguous assignment of this hypothetical protein as a NagZ. The identification and cloning of this NagZ may facilitate the development of strategies to circumvent resistance to beta-lactams in this human pathogen. As well, this general strategy, involving such 5-fluoro inactivators, may prove to be of general use for profiling proteomes and identifying glycoside hydrolases of medical importance or having desirable properties for biotechnology.

  DOI：

  10.1021/ja0763605
• 作为产物：
  描述：

  phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 IF₅-pyridine-HF 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride
  参考文献：
  名称：

  Synthesis of glycosyl fluorides from (phenylthio)glycosides using IF5–pyridine–HF

  摘要：

  IF5-pyridine-HF, an air- and moisture-stable fluorinating reagent, was applied to the synthesis of glycosyl fluorides from (phenylthio) glycosides. Common protecting groups of alcohol and diol can tolerate the reaction conditions performed, and therefore, the present method is applicable to the synthesis of various glycosyl fluorides. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.08.005

文献信息

• Synthesis of the root nodule-inducing factor NodRm-IV(C16:2,S) of rhizobium meliloti and related compounds
  作者：Shinji Ikeshita、Akio Sakamoto、Yuko Nakahara、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/s0040-4039(00)76846-8

  日期：1994.5

  Nod factors NodRm-IV(RCO,S) that carry natural as well as unnatural fatty acids were synthesized in a stereocontrolled manner.

  以立体控制的方式合成了携带天然和非天然脂肪酸的Nod因子NodRm-IV（RCO，S）。
• Catalytic and Stereoselective Glycosylation with Disarmed Glycosyl Fluoride Having Phthaloyl or Dichlorophthaloyl Protected Amino Function Using a 1 : 2 Combination of Stannic Chloride and Silver Tetrakis(pentafluorophenyl)borate
  作者：Hideki Jona、Hisashi Maeshima、Teruaki Mukaiyama

  DOI：10.1246/cl.2001.726

  日期：2001.7

  A catalytic and stereoselective glycosylation of various glycosyl acceptors with disarmed glycosyl fluorides having phthaloyl or dichlorophthaloyl protected amino function is successfully carried out by using a combination of stannic chloride (SnCl4) and silver tetrakis(pentafluorophenyl)borate [AgB(C6F5)4] in the coexistence of MS 5A, and the corresponding 1,2-trans disaccharides are obtained in high yields.

  通过使用氯化锡（SnCl4）和四氟苯基银四氟硼酸盐[AgB(C6F5)4]的组合，配合分子筛5A，可以成功催化和立体选择性地将各种糖苷受体与具有邻苯二甲酰保护氨基功能的弱活化糖苷氟化物进行糖苷化反应，得到相应的1,2-反式二糖，产率很高。
• A new method of anomeric protection and activation based on the conversion of glycosyl azides into glycosyl fluorides
  作者：Wolfgang Bröder、Horst Kunz

  DOI：10.1016/0008-6215(93)84071-d

  日期：1993.10

  Glycosyl azides provide reliable anomeric protection stable to conditions for hydrolytic removal of ester groups, for reductive opening or release of acetalic diol protection, for the introduction of ether-type protection, and for glycosylation processes. The utility of this anomeric protection is further enhanced as glycosyl azides may be converted into glycosyl fluorides, which can be activated for

  糖基叠氮化物提供稳定的可靠的端基异构保护，该条件稳定于以下条件：水解除去酯基，还原性打开或释放缩醛二醇保护，引入醚型保护以及糖基化过程。由于可将糖基叠氮化物转化为可被糖基化反应活化的糖基氟化物，因此进一步提高了该端基保护的效用。为此，已经将糖基叠氮化物与乙酰二羧酸二叔丁酯进行了1，3-偶极环加成。用氟化氢-吡啶配合物处理时，N-糖基三唑衍生物直接得到糖基氟化物。
• Synthesis of Multiantennary Complex Type<i>N</i>-Glycans by Use of Modular Building Blocks
  作者：Carlo Unverzagt、Gislinde Gundel、Steffen Eller、Ralf Schuberth、Joachim Seifert、Harald Weiss、Math��us Niemietz、Matthias Pischl、Claudia Raps

  DOI：10.1002/chem.200901908

  日期：2009.11.16

  developed for the synthesis of multiantennary N‐glycans of the complex type, which are commonly found on glycoproteins. The donor building blocks were laid out for the elongation of a core trisaccharide acceptor (β‐mannosyl chitobiose) conveniently protected with a single benzylidene moiety at the β‐mannoside. Through two consecutive regio‐ and stereoselective couplings the donors gave N‐glycans with three

  开发了一组模块化的寡糖构建基块，用于合成复杂类型的多天线N聚糖，这些糖通常在糖蛋白上发现。布置了供体结构单元，以延长核心三糖受体（β-甘露糖基壳二糖）的延伸，该受体方便地由β-甘露糖苷上的单个亚苄基部分保护。通过两个连续的区域和立体选择性偶联，供体以高产量获得了具有三到五个触角的N-聚糖。由于供体的保护基图案一致，可以通过使用一般的反应顺序对最终产物进行脱保护。
• GeCl₂·Dioxane–AgBF₄ Catalyzed Activation of Glycosyl Fluorides for Glycosylation
  作者：Qiuyu Zhu、Yu Tang、Biao Yu

  DOI：10.1021/acs.orglett.2c01146

  日期：2022.5.27

  catalytic glycosyl fluoride activation system using the GeCl2·dioxane–AgBF4 combination was developed, which involves a reversible activation of the anomeric C–F bond by a [Ge(II)–Cl]+ cation and a reversible chloride ion transfer between Ge(II) and glycosyl cations. This catalytic glycosylation system is easy to operate, proceeds at room temperature, and offers a broad scope of substrates.

  开发了一种使用 GeCl 2 ·二恶烷-AgBF 4组合的催化糖基氟化物活化系统，该系统涉及通过 [Ge(II)-Cl] +阳离子对异头 C-F 键的可逆活化和在它们之间的可逆氯离子转移。 Ge(II) 和糖基阳离子。这种催化糖基化系统易于操作，在室温下进行，并提供广泛的底物。