2,5-dioxopyrrolidin-1-yl-5-oxo-5-(prop-2-ynylamino)pentanoate | 693777-85-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,5-dioxopyrrolidin-1-yl-5-oxo-5-(prop-2-ynylamino)pentanoate
• 英文别名: succinimidyl N-propargyl glutariamidate；4-(Propargylcarbamoyl)butyric acid succinimidyl ester；(2,5-dioxopyrrolidin-1-yl) 5-oxo-5-(prop-2-ynylamino)pentanoate
• CAS: 693777-85-4
• 化学式: C₁₂H₁₄N₂O₅
• 分子量: 266.254
• InChiKey: JNLLPHKSRYIUBF-UHFFFAOYSA-N

物化性质

• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-dioxopyrrolidin-1-yl-5-oxo-5-(prop-2-ynylamino)pentanoate 、 2-[(2R,5R,8S,11S)-8-(4-aminobutyl)-5-benzyl-11-(3-guanidinopropyl)-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentazacyclopentadec-2-yl]acetic acid 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Tyrosine Bioconjugation through Aqueous Ene-Type Reactions: A Click-Like Reaction for Tyrosine

  摘要：

  A new and versatile class of cyclic diazodicarboxamides that reacts efficiently and selectively with phenols and the phenolic side chain of tyrosine through an ene-like reaction is reported. This mild aqueous tyrosine ligation reaction works over a broad pH range and expands the repertoire of aqueous chemistries available for small molecule, peptide, and protein modification. The tyrosine ligation reactions are shown to be compatible with the labeling of native enzymes and antibodies in a buffered aqueous Solution. This reaction provides a novel synthetic approach to bispecific antibodies. We believe this reaction will find broad utility in peptide and protein chemistry and in the chemistry of phenol-containing compounds.

  DOI：

  10.1021/ja909062q
• 作为产物：
  描述：

  戊二酸酐 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 2,5-dioxopyrrolidin-1-yl-5-oxo-5-(prop-2-ynylamino)pentanoate
  参考文献：
  名称：

  Living copolymer-protein/peptide hybrids for biomedical applications

  摘要：

  具有以下公式的水溶性聚合物被声明：Y-(L1)n1-(C(O))n2—(R1)n3—R2。这些聚合物可能包含多个水溶性、免疫原性降低的基团和多个活性基团。这些聚合物可能与蛋白质或含有最多十二个氨基酸的肽链相连接。

  公开号：

  US09242010B2

文献信息

• para-Hydrogenation of unsaturated moieties on poly(lysine) derived substrates for the development of novel hyperpolarized MRI contrast agents
  作者：Silvio Aime、Walter Dastrù、Roberto Gobetto、Alessandra Viale

  DOI：10.1039/b510693a

  日期：——

  unsaturation from the poly(lysine) backbone, the more intense the polarized signals when para-hydrogenation is carried out. This is due to (a) the maintenance of short reorientational times on the unsaturated ends, and therefore a sufficiently long T(1) of the protons added during hydrogenation, and (b) the minor effect of steric hindrance by the poly(lysine) backbone that decreases interaction of the

  合成了四种炔官能化的聚赖氨酸衍生物，并通过1H和13C NMR光谱进行了表征。在第一聚（赖氨酸）衍生物中，丙炔酸苯基部分直接结合到胺基臂上，而在其他衍生物中，炔丙基胺部分分别通过葡糖二酸和二甘醇（DG）链结合到胺基聚（赖氨酸）上。对炔基官能化的聚赖氨酸化合物的对氢加氢进行了研究，并就氢化产物的自旋晶格弛豫特性对结果进行了讨论。结果表明，将不饱和键与聚（赖氨酸）骨架分开的移动链越长，进行对位氢化时的极化信号越强。
• Tyrosine Bioconjugation through Aqueous Ene-Like Reactions
  申请人：Barbas, III Carlos F.

  公开号：US20120289682A1

  公开（公告）日：2012-11-15

  A new and versatile class of cyclic diazodicarboxamides that reacts efficiently and selectively with phenols and the phenolic side chain of tyrosine through an Ene-like reaction is reported. This mild aqueous tyrosine ligation reaction works over a broad pH range and expands the repertoire of aqueous chemistries available for small molecule, peptide, and protein modification. The tyrosine ligation reactions are shown to be compatible with the labeling of native enzymes and antibodies in buffered aqueous solution. This reaction provides a novel synthetic approach to bispecific antibodies. This reaction will find broad utility in peptide and protein chemistry and in the chemistry of phenol-containing compounds.

  报道了一种新型多功能环状二氮基二羧酰胺类化合物，通过Ene反应与苯酚和酪氨酸的苯基侧链高效选择性反应。这种温和的水相酪氨酸连接反应适用于广泛的pH范围，并扩展了小分子、肽和蛋白质修饰的水相化学反应库。该酪氨酸连接反应可与缓冲水溶液中的天然酶和抗体标记兼容。该反应提供了一种新的双特异性抗体合成方法。该反应将在肽和蛋白质化学以及含酚化合物的化学中发挥广泛的实用价值。
• Living Copolymer-Protein/Peptide Hybrids for Biomedical Applications
  申请人：Raja Krishnaswami

  公开号：US20110262991A1

  公开（公告）日：2011-10-27

  Water soluble polymers having formula I: Y-(L 1 ) ni -(C(O)) n2 —(R 1 ) n3 —R 2 are claimed. The polymers may contain multiple water soluble, immunogenicity reducing moieties and multiple active moieties. The polymers may be linked to a protein, or a peptide having up to twelve amino acids.

  具有I式的水溶性聚合物：Y-(L1)ni-(C（O）)n2—（R1）n3—R2被声明。这些聚合物可以包含多个水溶性、免疫原性降低的基团和多个活性基团。这些聚合物可以与具有多达十二个氨基酸的蛋白质或肽连接。
• Oligosaccharides and Peptide Displayed on an Amphiphilic Polymer Enable Solid Phase Assay of Hapten Specific Antibodies
  作者：David R. Bundle、Pui-Hang Tam、Huu-Anh Tran、Eugenia Paszkiewicz、Jonathan Cartmell、Joanna M. Sadowska、Susmita Sarkar、Maju Joe、Pavel I. Kitov

  DOI：10.1021/bc400486w

  日期：2014.4.16

  Copovidone, a copolymer of vinyl acetate and N-vinyl-2-pyrrolidone, was synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization, and after deacetylation the polymer was functionalized by introduction of amino, azide, and alkyne pendant groups to allow attachment of glycans and peptide. Candida albicans beta-mannan trisaccharides 1 and 2 and M. tuberculosis arabinan hexasaccharide 3 with appropriate tethers were conjugated to the polymers by squarate or click chemistry. C. albicans T-cell peptide 4 bearing a C-terminal epsilon-azidolysine was also conjugated to copovidone by click chemistry. The resulting conjugates provide convenient non-protein-based antigens that are readily adsorbed on ELISA plates, and display excellent characteristics for assay of antibody binding to the haptenic group of interest. Copovidone and BSA glycoconjugates exhibited similar adsorption characteristics when used to coat ELISA plates, and both conjugates were optimal when used as coating solutions at low nanogram/mL concentrations. Provided that the copovidone conjugated glycan is stable to acid, assay plates can be easily processed for reuse at least three times without detectable variation or degradation in ELISA readout.
• Chemically Programmed Vaccination
  申请人：Barbas, III Carlos F.

  公开号：US20110311516A1

  公开（公告）日：2011-12-22

  Provided herein is a method for chemically programmed vaccination. Methods include inducing a covalent-binding polyclonal antibody response in a subject and programming the polyclonal response with a targeting compound.