N-propargyloxycarbonyloxy succinimide | 484064-96-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-propargyloxycarbonyloxy succinimide
• 英文别名: propargyl carbonate N-hydroxysuccinimide ester；2,5-dioxopyrrolidin-1-yl prop-2-yn-1-yl carbonate；N-(Propargyloxycarbonyloxy)succinimide；(2,5-dioxopyrrolidin-1-yl) prop-2-ynyl carbonate
• CAS: 484064-96-2
• 化学式: C₈H₇NO₅
• 分子量: 197.147
• InChiKey: LLKBWEDCWCHGMC-UHFFFAOYSA-N

物化性质

• 熔点：
  107 °C
• 沸点：
  276.6±42.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-propargyloxycarbonyloxy succinimide 、 BOC-L-亮氨酸 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以15%的产率得到(S)-prop-2-yn-1-yl 2-((tert-butoxycarbonyl)amino)-4-methylpentanoate
  参考文献：
  名称：

  Simultaneous Protection and Activation of Amino Acids Using Propargyl Pentafluorophenyl Carbonate

  摘要：

  A very efficient method for the simultaneous protection of the amino group and activation of the carboxyl group of amino acids is reported using propargyl pentafluorophenyl carbonate (PocOPfp). The amino group is protected as a propargyloxycarbonyl (Poc) derivative, and the carboxyl group is activated as a pentafluorophenyl ester. The yields obtained are good to excellent ranging from 60 to 87%.

  DOI：

  10.1021/ol060494q
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 炔丙基氯甲酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以92%的产率得到N-propargyloxycarbonyloxy succinimide
  参考文献：
  名称：

  Simultaneous Protection and Activation of Amino Acids Using Propargyl Pentafluorophenyl Carbonate

  摘要：

  A very efficient method for the simultaneous protection of the amino group and activation of the carboxyl group of amino acids is reported using propargyl pentafluorophenyl carbonate (PocOPfp). The amino group is protected as a propargyloxycarbonyl (Poc) derivative, and the carboxyl group is activated as a pentafluorophenyl ester. The yields obtained are good to excellent ranging from 60 to 87%.

  DOI：

  10.1021/ol060494q

文献信息

• Click and Pick: Identification of Sialoside Analogues for Siglec-Based Cell Targeting
  作者：Cory D. Rillahan、Erik Schwartz、Ryan McBride、Valery V. Fokin、James C. Paulson

  DOI：10.1002/anie.201205831

  日期：2012.10.29

  Click ‘n’ chips: Azide and alkyne‐bearing sialic acids (purple diamond; see picture) were subjected to high‐throughput click chemistry to generate a library of sialic acid analogues. Microarray printing of the library and screening with the siglec family of sialic‐acid‐binding proteins, led to the identification of high‐affinity ligands for siglec‐9 and siglec‐10.

  Click 'n' 芯片：叠氮化物和含炔的唾液酸（紫色菱形；见图）经过高通量点击化学生成唾液酸类似物库。文库的微阵列打印和 siglec 唾液酸结合蛋白家族的筛选，导致了 siglec-9 和 siglec-10 的高亲和力配体的鉴定。
• [EN] NEW POTENT SIALYLTRANSFERASE INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS PUISSANTS DE SIALYLTRANSFÉRASE
  申请人：STICHTING KATHOLIEKE UNIV

  公开号：WO2019145562A1

  公开（公告）日：2019-08-01

  The present invention relates to anew class of sialyltransferase inhibitors. The class features a carbamate or similar moiety on the amine of a neuraminic acid derivative. Such inhibitors are suitable for use as a medicament, for example for treating, preventing, or delaying bacterial infection, viral infection, cancer, a disorder of sialic acid metabolism, or an autoimmune disease.

  本发明涉及一种新型唾液酸转移酶抑制剂类。该类别在神经氨酸衍生物的胺基上具有氨基甲酸酯或类似的基团。这种抑制剂适用于用作药物，例如用于治疗、预防或延缓细菌感染、病毒感染、癌症、唾液酸代谢紊乱或自身免疫疾病。
• Synthesis and Functionalization of Azetidine‐Containing Small Macrocyclic Peptides
  作者：George J. Saunders、Sam A. Spring、Eleanor Jayawant、Ina Wilkening、Stefan Roesner、Guy J. Clarkson、Ann M. Dixon、Rebecca Notman、Michael Shipman

  DOI：10.1002/chem.202400308

  日期：——

  Incorporation of a 3-aminoazetidine (3-AAz) into peptide backbones improves head-to-tail cyclizations compared to unmodified peptides. The azetidine nitrogen can be readily functionalized using substitution or click chemistry. Crystal structure analysis reveals that a 3-AAz modified cyclic tetrapeptide adopts an uncommon all-trans conformation. The 3-AAz provides stability to protease degradation compared

  与未修饰的肽相比，将 3-氨基氮杂环丁烷 (3-AAz) 掺入肽主链可改善头尾环化。使用取代或点击化学可以容易地对氮杂环丁烷氮进行官能化。晶体结构分析表明，3-AAz 修饰的环状四肽采用不常见的全反式构象。与未修饰的大环化合物相比，3-AAz 为蛋白酶降解提供了稳定性。
• A Multifunctional <i>Pasteurella multocida</i> Sialyltransferase:  A Powerful Tool for the Synthesis of Sialoside Libraries
  作者：Hai Yu、Harshal Chokhawala、Rebekah Karpel、Hui Yu、Bingyuan Wu、Jianbo Zhang、Yingxin Zhang、Qiang Jia、Xi Chen

  DOI：10.1021/ja0561690

  日期：2005.12.1

  A multifunctional sialyltransferase has been cloned from Pasteurella multocida strain P-1059 and expressed in E. coli as a truncated C-terminal His6-tagged recombinant protein (tPm0188Ph). Biochemical studies indicate that the obtained protein is (1) an alpha2,3-sialyltransferase (main function), (2) an alpha2,6-sialyltransferase, (3) an alpha2,3-sialidase, and (4) an alpha2,3-trans-sialidase. The recombinant tPm0188Ph is a powerful tool in the synthesis of structurally diverse sialoside libraries due to its relaxed substrate specificity, high solubility, high expression level, and multifunctionality.
• NEW POTENT SIALYLTRANSFERASE INHIBITORS
  申请人：Stichting Katholieke Universiteit

  公开号：EP3746457A1

  公开（公告）日：2020-12-09