3-bromopropyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside | 595568-97-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-bromopropyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: 3-bromopropyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside
• CAS: 595568-97-1
• 化学式: C₁₇H₂₆BrNO₉
• 分子量: 468.299
• InChiKey: JXUUOZDCFHFJAT-WRQOLXDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.44
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  126.46
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-bromopropyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 sodium azide 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 3-azidopropyl 2-acetylamino-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of the sialyl-α-(2→3′)-lactosamine trisaccharide with a 3-aminopropyl group as a spacer at the reducing end

  摘要：

  The trisaccharide, 3-aminopropyl 5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto -2-nonulopyranosylonic acid-(2 --> 3)-beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside has been synthesized chemoenzymatically for the first time. First, the acceptor, 3-aminopropyl beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside was synthesized in a conventional chemical manner, and then it was coupled with CMP-sialic acid using alpha-(2 --> 3)-(N)-sialyltransferase to afford the desired trisaccharide by an enzymatically stereocontrolled manner. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00167-8
• 作为产物：
  描述：

  2-methyl-(2-acetamido-3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyrano)-<2,1-d>-2-oxazoline 、 3-溴-1-丙醇 在 copper(ll) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以57%的产率得到3-bromopropyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Introducing affinity and selectivity into galectin-targeting nanoparticles with fluorinated glycan ligands

  摘要：

  采用化学酶法的位点特异性氟化策略，获得具有可调选择性的糖基纳米颗粒以对抗半乳糖结合蛋白。

  DOI：

  10.1039/d0sc05360k

文献信息

• Synthesis of mono- and disaccharide analogs of moenomycin and lipid II for inhibition of transglycosylase activity of penicillin-binding protein 1b
  作者：Sylvie Garneau、Lei Qiao、Lan Chen、Suzanne Walker、John C. Vederas

  DOI：10.1016/j.bmc.2004.09.019

  日期：2004.12

  Three types of mono- and disaccharides 3a,b, 4a-c, 5, and some chaetomellic acid A analogs 6 and 42-44 were synthesized as potential inhibitors of the transglycosylase activity of penicillin-binding protein 1b (PBP1b), a key bacterial enzyme responsible for the formation of the polysaccharide backbone of peptidoglycan as well as for cross-linking of its peptide portions. The target compounds combine

  合成了三种类型的单糖和二糖3a，b，4a-c，5和一些chaetomellic acid A类似物6和42-44，它们可能是关键细菌青霉素结合蛋白1b（PBP1b）的糖基转移酶活性的抑制剂。负责肽聚糖多糖主链形成及其肽部分交联的酶。目标化合物结合了莫诺霉素活性部分和天然PBP1b底物脂质II的结构特征。以收敛的方式获得所需的骨架，该方式涉及将脂烷基化的甘油酸部分11a，b连接至相应的含碳水化合物的膦酸23、24a和24b。制备化合物3a，b以验证糖与不可裂解的C-膦酸酯部分之间的距离要求。合成了化合物4a-c，以检验moenomycin的第一个糖单元（一种已知的PBP1b转糖基酶催化抑制剂）相对于抗生素活性的重要性。它们是通过以下方法制备的：将11a，b与28a和28c缩合，这些缩合是通过将3-溴丙醇与恶唑啉25a，b糖基化，然后将Arbuzov与亚磷酸三乙酯或亚磷酸三甲酯反应，然后再与溴
• H2SO4-Silica Promoted Direct Formation of β-Glycosides of N-Acetyl Glycosylamines under Microwave Conditions
  作者：Balaram Mukhopadhyay、Santanu Mandal、Nayan Sharma

  DOI：10.1055/s-0029-1218304

  日期：2009.12

  N-Acetyl glycosamines are important building blocks for the synthesis of biologically active oligosaccharides. This communication describes a simple direct protocol for the synthesis of β-glycosides of N-acetyl glycosylamines from easily accessible per-O-acetyl derivatives of of N-acetyl glycosylamines using H2SO4-silica as promoter under microwave conditions. The protocol is suitable for alcohol or sugar acceptors.

  N-乙酰氨基糖是生物活性低聚糖合成的重要构建单元。本通信介绍了一种简单直接的方法，利用微波条件下以硫酸-硅胶为促进剂，从易得的N-乙酰氨基糖的全O-乙酰衍生物合成N-乙酰氨基糖的β-糖苷。该方法适用于醇或糖类受体。
• Enzymatic synthesis of <i>N</i>-acetyllactosamine from lactose enabled by recombinant β1,4-galactosyltransferases
  作者：Kun Huang、Fabio Parmeggiani、Helene Ledru、Kristian Hollingsworth、Jordi Mas Pons、Andrea Marchesi、Peter Both、Ashley P. Mattey、Edward Pallister、Gregory S. Bulmer、Jolanda M. van Munster、W. Bruce Turnbull、M. Carmen Galan、Sabine L. Flitsch

  DOI：10.1039/c9ob01089k

  日期：——

  Synthesis of LacNAc with reversible GalTs.

  使用可逆的GalTs合成LacNAc。
• Ionic-liquid-based catch and release mass spectroscopy tags for enzyme monitoring
  作者：M. Carmen Galan、Anh Tuan Tran、Claire Bernard

  DOI：10.1039/c0cc04224b

  日期：——

  A novel, inexpensive and versatile ionic-liquid-based catch and release mass spectrometry tag (I-Tag) that facilitates substrate purification, fast, robust and sensitive enzymatic reaction monitoring and quantitative kinetic analysis has been developed. The applicability of the system has been demonstrated in an enzymatic assay with beta-1,4-galactosyltransferase.

  已经开发了一种新型，廉价且通用的基于离子液体的捕获和释放质谱标签（I-Tag），该标签可促进底物纯化，快速，稳定和灵敏的酶促反应监测以及定量动力学分析。该系统的适用性已在使用β-1,4-半乳糖基转移酶的酶促测定中得到证实。