N-羟基-2,3:5,6-二-O-(1-甲基亚乙基)-alpha-D-式闭式式呋喃葡萄糖基胺结构 | 1226812-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N-羟基-2,3:5,6-二-O-(1-甲基亚乙基)-alpha-D-式闭式式呋喃葡萄糖基胺结构
• 英文名称: N-Hydroxy-2,3:5,6-bis-O-(1-methylethylidene)-alpha-D-glucofuranosylamine
• 英文别名: N-[(3aR,4R,6S,6aR)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]hydroxylamine
• CAS: 1226812-52-7
• 化学式: C₁₂H₂₁NO₆
• 分子量: 275.302
• InChiKey: FLWZKKRGBHCGBS-JDDHQFAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  78.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-羟基-2,3:5,6-二-O-(1-甲基亚乙基)-alpha-D-式闭式式呋喃葡萄糖基胺结构 在 magnesium sulfate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.5h， 生成 (S)-4,4-dichloro-2-((3aR,4R,6S,6aR)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-3-isopropylisoxazolidin-5-one
  参考文献：
  名称：

  α,α-Dichloroisoxazolidinones for the Synthesis and Chemoselective Peptide Ligation of α-Peptide α-Ketoacids

  摘要：

  In seeking to develop an iterative approach to the preparation of alpha-oligopeptides by the chemoselective amide-forming coupling of alpha-ketoacids and hydroxylamines, we have designed and synthesized novel enantiopure monomers. Key to our approach is the use of alpha,alpha-dichloroacids as masked alpha-ketoacids. The preparation of these monomers, their coupling with alpha-ketoacids, and the conversion of the alpha,alpha-dichloroacids to alpha-ketoacids is described. These studies provide a first step to a conceptually unique approach to peptide synthesis that does not require activating reagents or produce chemical byproducts.

  DOI：

  10.3987/com-10-s(e)106

文献信息

• Antibiotic Discovery with Synthetic Fermentation: Library Assembly, Phenotypic Screening, and Mechanism of Action of β-Peptides Targeting Penicillin-Binding Proteins
  作者：Iain A. Stepek、Trung Cao、Anika Koetemann、Satomi Shimura、Bernd Wollscheid、Jeffrey W. Bode

  DOI：10.1021/acschembio.9b00227

  日期：2019.5.17

  focused screening, and structure-activity relationship studies led to the identification of a potent antimicrobial peptide, showing strong selectivity for our model system Bacillus subtilis over human HEK293 cells. To determine the antibacterial mechanism of action, a peptide probe bearing a photoaffinity tag was readily synthesized through the use of appropriate synthetic fermentation building blocks

  与导致生物活性天然产物的生物合成途径类似，合成发酵在水性，生物相容性条件下从简单的结构单元生成分子混合物，从而可以直接筛选所得培养物中的生物活性。在这项工作中，使用合成发酵平台成功鉴定了新型β肽抗生素。表型筛选以最初随机的方式进行，可以轻松鉴定活性培养物。随后的解卷积，重点筛选和结构-活性关系研究导致了一种有效的抗菌肽的鉴定，显示了我们的模型系统枯草芽孢杆菌对人HEK293细胞具有很强的选择性。为了确定抗菌作用机理，通过使用适当的合成发酵构件，可以轻松合成带有光亲和标签的肽探针，并使用基于定量质谱的策略将其用于靶标鉴定。化学旋转方法导致鉴定出许多细菌膜蛋白作为预期靶标。这些发现通过使用微尺度热泳的与青霉素结合蛋白4的结合亲和力研究得到验证，其中生物活性肽显示出纳摩尔摩尔范围内的解离常数（Kd）。通过这些努力，我们为此处介绍的合成发酵方法提供了概念验证，这是新型生物活性化合物表型发现的新策略。
• Asymmetric synthesis of enantiopure isoxazolidinone monomers for the synthesis of β3-oligopeptides by chemoselective amide ligation
  作者：M. Elisa Juarez-Garcia、Shouyun Yu、Jeffrey W. Bode

  DOI：10.1016/j.tet.2010.04.016

  日期：2010.6

  of enantiopure isoxazolidinone monomers as precursors for the preparation of enantiopure N-terminal hydroxylamine–β3-oligopeptides, which may be used as reaction partners with α-ketoacids in the decarboxylative amide ligation reaction, is described.

  对映体纯异恶唑烷酮单体作为用于制备对映体纯的N-末端羟胺-β前体的设计和一般合成3 -oligopeptides，其可被用作具有在脱羧酰胺连接反应α酮酸反应伙伴，进行说明。
• METHOD FOR THE GENERATION OF CHEMICAL LIBRARIES
  申请人：ETH ZURICH

  公开号：US20170088878A1

  公开（公告）日：2017-03-30

  A method for the generation of oligomers or a mixture of oligomers to form a chemical library by amide-forming oligomerization comprises the steps of 1) reacting a mixture of at initiator (I) with monomer (M) to form a dimer of the initiator (I) and the monomer (M) or a pre-oligomer with an initiator (I) attached to a chain of more than one monomer (M) or a mixture thereof by amide-bond formation; 2) optionally adding at least one terminator (T) for the formation of a linear oligomer or a mixture of linear oligomers by amide-bond formation; or, for the formation of a cyclic oligomer or a mixture of cyclic oligomers by amide-bond formation, changing the reaction conditions relative to step 1) so as to form a linking covalent bond between the at least one initiator (I).
• α,α-Dichloroisoxazolidinones for the Synthesis and Chemoselective Peptide Ligation of α-Peptide α-Ketoacids
  作者：Jeffrey W. Bode、Tetsuo Narumi

  DOI：10.3987/com-10-s(e)106

  日期：——

  In seeking to develop an iterative approach to the preparation of alpha-oligopeptides by the chemoselective amide-forming coupling of alpha-ketoacids and hydroxylamines, we have designed and synthesized novel enantiopure monomers. Key to our approach is the use of alpha,alpha-dichloroacids as masked alpha-ketoacids. The preparation of these monomers, their coupling with alpha-ketoacids, and the conversion of the alpha,alpha-dichloroacids to alpha-ketoacids is described. These studies provide a first step to a conceptually unique approach to peptide synthesis that does not require activating reagents or produce chemical byproducts.