γ-propargyl L-glutamate N-carboxyanhydride | 1204576-46-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: γ-propargyl L-glutamate N-carboxyanhydride
• 英文别名: prop-2-ynyl 3-[(4S)-2,5-dioxo-1,3-oxazolidin-4-yl]propanoate
• CAS: 1204576-46-4
• 化学式: C₉H₉NO₅
• 分子量: 211.174
• InChiKey: UTZBUOWQDFTSHP-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  δ-propargyl-L-glutamic acid hydrochloride 在 三光气 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到γ-propargyl L-glutamate N-carboxyanhydride
  参考文献：
  名称：

  Synthesis and Self-assembly of Amphiphilic Homoglycopolypeptide

  摘要：

  The synthesis of the amphiphilic homoglycopolypeptide was carried out by a combination of NCA polymerization and click chemistry to yield a well-defined Polypeptide having an amphiphilic carbohydrate on its side chain. The amphiphilicity of the carbohydrate was achieved by incorporation of an alkyl chain, at the C-6 position of the carbohydrate thus also rendering the homoglycopolypeptide amphiphilic. The homoglycopolypeptide formed multimicellar aggregates in water above a critical concentration of 0.9 mu M due to phase separation. The multimicellar aggregates were characterized by DLS, TEM, and AFM. It is proposed that hydrophobic interactions of the aliphatic chains at the 6-position of the sugar moieties drives the assembly of these rod-like homoglycopolypeptide into large;spherical aggregates. These multimicellar aggregates encapsulate both hydrophilic as well as hydrophobic dye as was confirmed by confocal microscopy. finally, amphiphilic random polypeptides containing 10% and 20% alpha-D-mannose in addition to glucose containing a, hydrophobic alkyl chain at its 6 position were synthesized by our methodology, and these polymers Were also found to assemble into spherical nanostructures. The spherical assemblies Of amphiphilic random glycopolypeptides containing 10% and 20% mannose were found to be surface bioactive and were found, to interact with the lectin Con-A.

  DOI：

  10.1021/la400144t

文献信息

• The synthetic tuning of clickable pH responsive cationic polypeptides and block copolypeptides
  作者：Amanda C. Engler、Daniel K. Bonner、Hilda G. Buss、Eva Y. Cheung、Paula T. Hammond

  DOI：10.1039/c1sm05064h

  日期：——

  A series of pH responsive synthetic polypeptides has been developed based on an N-carboxyanhydride ring opening polymerization combined with a facile and versatile click chemistry. Poly(γ-propargyl L-glutamate) (PPLG) homopolymers and poly(ethylene glycol-b-γ-propargyl L-glutamate) (PEG-b-PPLG) block copolymers were substituted with various amine moieties that range in pKa and hydrophobicity, providing the basis for a library of new synthetic structures that can be tuned for specific interactions and responsive behaviors. These amine-functionalized polypeptides have the ability to change solubility, or reversibly self-assemble into micelles with changes in the degree of ionization; they also adopt an α-helical structure at biologically relevant pHs. Here we characterize the pH responsive behavior of the new polypeptides and the hydrolysis of the ester containing amine side chains. We examine the reversible micellization with block copolymers of the polypeptides and nucleic acid encapsulation that demonstrate the potential use of these materials for systemic drug and gene delivery.

  基于环状酸酐的开环聚合以及简便且通用的点击化学，已经开发了一系列pH响应性合成多肽。聚（γ-炔丙基-L-谷氨酸）（PPLG）均聚物和聚（乙二醇-b-γ-炔丙基-L-谷氨酸）（PEG-b-PPLG）嵌段共聚物被各种具有不同pKa值和疏水性的氨基取代，为新合成结构的库提供了基础，可以针对特定相互作用和响应行为进行调节。这些氨基功能化多肽能够改变溶解性，或在电离程度变化时可逆地自组装成胶束；它们在生物相关的pH值下还具有α-螺旋结构。在这里，我们表征了新多肽的pH响应行为以及含有氨基侧链的酯的水解。我们检查了多肽嵌段共聚物的可逆胶束化以及核酸包封，这些研究表明了这些材料在全身药物和基因传递中的潜在用途。
• Facile functionalization of polypeptides by thiol-yne photochemistry for biomimetic materials synthesis
  作者：Yugang Huang、Yonghong Zeng、Jianwen Yang、Zhaohua Zeng、Fangming Zhu、Xudong Chen

  DOI：10.1039/c1cc12177d

  日期：——

  Rapid and highly efficient side-chain functionalization of polypeptides was achieved via combination of ring-opening polymerization of a new clickable monomer of γ-propargyl-L-glutamateN-carboxyanhydride (PLG-NCA) and thiol-yne photochemistry, which provides a convenient and universal route to prepare diverse polypeptide-based biomimetic hybrid materials.

  通过γ-丙炔基-L-谷氨酸-N-羧基酸酐（PLG-NCA）新型可点击单体的开环聚合与硫醇-炔光化学的结合，实现了多肽侧链的快速、高效官能化，为制备基于多肽的多种生物仿生杂化材料提供了一条便捷、通用的途径。
• DNA-Grafted Polypeptide Molecular Bottlebrush Prepared via Ring-Opening Polymerization and Click Chemistry
  作者：Ping Chen、Chuang Li、Dongsheng Liu、Zhibo Li

  DOI：10.1021/ma302233m

  日期：2012.12.21

  A new type of DNA grafted polypeptide molecular brush was synthesized via a combination of ring-opening polymerization (ROP) and click chemistry. This conjugation method provides an easy and efficient approach to obtain a hybrid DNA-grafted polypeptide molecular bottlebrush. The structure and assembly behaviors of this hybrid brush were investigated using electrophoresis, UV–vis spectroscopy, transmission

  通过开环聚合（ROP）和点击化学的结合，合成了一种新型的DNA接枝多肽分子刷。这种缀合方法提供了一种简单而有效的方法来获得杂化的DNA嫁接的多肽分子牙刷。使用电泳，紫外可见光谱，透射电子显微镜（TEM）和原子力显微镜（AFM）对这种混合刷的结构和组装行为进行了研究。可以通过两种含有互补DNA侧链的多肽-g- DNA分子刷的杂交获得分层的超分子装配体。我们进一步证明，这种多肽-摹-DNA可与ds-DNA和DNA接枝的金纳米颗粒杂交以分别形成超分子刷和杂化刷。另外，可以通过使多肽-g -DNA与接头-ds-DNA杂交来制备DNA-多肽水凝胶，所述接头-ds-DNA包含互补的“粘性末端”以用作交联剂。
• Nucleopolypeptides with DNA-triggered α helix-to-β sheet transition
  作者：Michel Nguyen、Jean-Luc Stigliani、Genevieve Pratviel、Colin Bonduelle

  DOI：10.1039/c7cc03472e

  日期：——

  Nucleopolypeptide polymers are a new class of smart materials that exhibit selective structuring switch upon DNA binding.

  核聚肽聚合物是一种新型的智能材料，它在与DNA结合时表现出选择性的结构转变。
• Helix versus coil polypeptide macromers: gel networks with decoupled stiffness and permeability
  作者：Abigail M. Oelker、Shannon M. Morey、Linda G. Griffith、Paula T. Hammond

  DOI：10.1039/c2sm26487k

  日期：——

  hypothesized that a random copolymer (PPDLG) with equal amounts of γpLglu and γ-propargyl-D-glutamate (γpDglu) monomers would exhibit a more flexible random coil conformation. The resulting macromers exhibited narrow molecular weight distributions (PDI = 1.15) and were grafted with ethylene glycol groups using a highly efficient “click” azide/alkyne cycloaddition reaction with average grafting efficiency of 97%

  作为研究基质刚度、渗透性和配体密度对细胞行为的个体影响的平台，我们开发了一组水凝胶，其刚度由聚合物主链刚度调节，与交联密度和浓度无关。先前的研究报道，通过γ-炔丙基-L-谷氨酸(γp L glu)的N-羧酸酐开环聚合合成的聚(炔丙基-L-谷氨酸)(PPLG) ，采用刚性a-螺旋构象：我们假设具有等量 γp L glu 和 γ-炔丙基-D-谷氨酸 (γp D glu) 单体的无规共聚物 (PPDLG) 将表现出更灵活的无规卷曲构象。所得大分子单体表现出窄分子量分布（PDI = 1.15），并使用高效的“点击”叠氮化物/炔环加成反应接枝乙二醇基团，PPLG 的平均接枝效率为 97%，PPDLG 的平均接枝效率为 85%。通过圆二色光谱、FTIR 光谱和动态光散射表征的多肽二级结构确实取决于单体手性：PPLG 表现出 α-螺旋构象，而 PPDLG 采用无规卷曲构象。分析通过螺旋或无规卷曲多肽与聚乙二醇