δ-propargyl-L-glutamic acid hydrochloride | 1204576-45-3

• 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: δ-propargyl-L-glutamic acid hydrochloride
• 英文别名: γ-propargyl-L-glutamic acid hydrochloride；γ-propargyl L-glutamate hydrochloride；propargyl-L-glutamate
• CAS: 1204576-45-3
• 化学式: C₈H₁₁NO₄*ClH
• 分子量: 221.641
• InChiKey: UBZMJUSXDWHBEZ-RGMNGODLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.22
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.62
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  L-谷氨酸盐酸盐 、 2-丙炔-1-醇 在 三甲基氯硅烷 作用下， 反应 49.0h， 以66%的产率得到δ-propargyl-L-glutamic acid hydrochloride
  参考文献：
  名称：

  Nucleopolypeptides with DNA-triggered α helix-to-β sheet transition

  摘要：

  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。

  DOI：

  10.1039/c7cc03472e

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。
• [EN] A TAG FOR LABELING BIOMOLECULES<br/>[FR] ÉTIQUETTE POUR MARQUER DES BIOMOLÉCULES
  申请人：SHANGHAI POLARIS BIOLOGY CO LTD

  公开号：WO2020228734A1

  公开（公告）日：2020-11-19

  Provided is a tag for labeling a biomolecule, comprising a polymer backbone, one or more pendant moieties, and an end group capable of binding to the biomolecule, wherein each of the pendant moieties is attached to the polymer backbone and capable of chelating with an element. Also provided is a conjugate, comprising a biomolecule covalently coupled with the tag.

  提供了一种用于标记生物分子的标签，包括聚合物骨架，一个或多个侧基团和一个能够与生物分子结合的末端基团，其中每个侧基团连接到聚合物骨架并能够与元素螯合。同时提供了一个共轭物，其中包括与标签共价耦合的生物分子。
• Stable Aqueous Dispersions of Glycopeptide-Grafted Selectably Functionalized Magnetic Nanoparticles
  作者：Tushar Borase、Tsedev Ninjbadgar、Antonios Kapetanakis、Sandra Roche、Robert O'Connor、Christian Kerskens、Andreas Heise、Dermot F. Brougham

  DOI：10.1002/anie.201208099

  日期：2013.3.11

  Suspensions of glycopeptide grafted magnetic nanoparticles can be produced by N‐carboxyanhydride ring‐opening polymerization with subsequent click glycosylation. The resulting materials have a high sugar density, optimal dispersion and T1‐weighted MRI properties, and bio‐recognition ability. The approach can be used to attach any type or combination of functional groups, the density of which is not

  甜甜的纳米磁铁：糖肽接枝的磁性纳米颗粒的悬浮液可通过N-羧基酐开环聚合反应以及随后的点击糖基化作用制得。所得材料具有高糖密度，最佳分散性和T 1加权MRI特性，并具有生物识别能力。该方法可用于连接官能团的任何类型或组合，官能团的密度不受颗粒表面积的限制。
• 一种双佐剂-新抗原肿瘤纳米疫苗及其制备方法和应用
  申请人：莎穆（上海）生物科技有限公司

  公开号：CN111068047A

  公开（公告）日：2020-04-28

  本发明提供一种纳米疫苗，它是同时装载有肿瘤新生抗原及其两种佐剂的纳米颗粒。本发明还提供用于制备所述纳米疫苗的一种组合物，包括小分子佐剂R848、末端修饰马来酰胺键的含聚乙二醇链段的两亲性二嵌段聚合物、核酸佐剂CpG、聚乙二醇修饰的聚多肽和肿瘤新生抗原。本发明的纳米疫苗在体内外均有显著的免疫激活效果以及良好的抗原特异性肿瘤抑制效果。本发明还提供制备所述纳米疫苗的方法及所述纳米疫苗在制备肿瘤疫苗药物中的应用。
• Highly Efficient “Grafting onto” a Polypeptide Backbone Using Click Chemistry
  作者：Amanda C. Engler、Hyung-il Lee、Paula T. Hammond

  DOI：10.1002/anie.200904070

  日期：2009.11.23

  “Clicked” into place: Densely grafted poly(γ‐propargyl‐L‐glutamate)‐g‐poly(ethylene glycol) polypeptides have been synthesized by combining ring‐opening polymerization of N‐carboxyanhydrides with click chemistry. Various lengths of poly(ethylene glycol) (PEG) side chains (750 g mol−1 to 5000 g mol−1) were attached to a rigid α‐helical poly(γ‐propargyl‐L‐glutamate); extremely high grafting efficiencies

  “点击”到位：通过将N-羧酸酐的开环聚合与点击化学结合，合成了密集接枝的聚（γ-炔丙基-L-谷氨酸）-g-聚（乙二醇）多肽。不同长度的聚（乙二醇）（PEG）侧链（750 g mol -1至 5000 g mol -1）连接到刚性 α-螺旋聚（γ-炔丙基-L-谷氨酸）；实现了超过 96% 的极高接枝效率。