L-allylglycine N-carboxyanhydride | 166540-71-2

• 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: L-allylglycine N-carboxyanhydride
• 英文别名: L-allylglycine-NCA；(S)-4-Allyloxazolidine-2,5-dione；(4S)-4-prop-2-enyl-1,3-oxazolidine-2,5-dione
• CAS: 166540-71-2
• 化学式: C₆H₇NO₃
• 分子量: 141.126
• InChiKey: NOIUGLVEFSUGKF-BYPYZUCNSA-N

物化性质

• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-(-)-2-氨基-4-戊烯酸 、 三光气 在 Pinene 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以57%的产率得到L-allylglycine N-carboxyanhydride
  参考文献：
  名称：

  pH-Responsive Bioactive Glycopolypeptides with Enhanced Helicity and Solubility in Aqueous Solution

  摘要：

  Copolypeptides of L-glutamate and glucosylated L-/DL-allyl- or DL-propargylglycine were synthesized by ring opening polymerization and thiol-ene/yne photochemistry in aqueous solution, allowing the mild introduction. of sugar units (here, glucose) in the final step. The glucosylatecl and non-glucosylated samples adopt a random coil conformation in neutral and basic media and an alpha-helical conformation in acidic media, the helical content depending on the number and configuration of allyl-/propargylglycine units. The glucocopolypeptides unveil enhanced helical stability and solubility down to pH 3.5. Turbidity assays proved the selective binding of the polymers to the plant lectin concanavalin A.

  DOI：

  10.1021/ja308772d

文献信息

• Rapid and Mild Synthesis of Amino Acid <i>N</i> -Carboxy Anhydrides: Basic-to-Acidic Flash Switching in a Microflow Reactor
  作者：Yuma Otake、Hiroyuki Nakamura、Shinichiro Fuse

  DOI：10.1002/anie.201803549

  日期：2018.8.27

  Polymerization of N‐carboxy anhydrides (NCAs) is the primary process used to prepare polypeptides. The synthesis of various pure NCAs is key to the efficient synthesis of polypeptides. The only practical method that can be used to synthesize NCAs requires harsh acidic conditions that make acid‐labile substrates unusable and results in an undesired ring opening of NCAs. Basic‐to‐acidic flash switching

  N的聚合‐羧酸酐（NCA）是用于制备多肽的主要过程。各种纯净NCA的合成是有效合成多肽的关键。唯一可用于合成NCA的实用方法要求苛刻的酸性条件，使酸不稳定的底物无法使用，并导致NCA出现不希望的开环。在微流反应器中使用从碱性到酸性的闪蒸切换和随后的闪蒸稀释技术来演示NCA的合成。它既快速（0.1 s）又温和（20°C），并且包括含有酸不稳定官能团的底物。从基本到酸性的闪光切换既可以加速所需的NCA形成，又可以避免NCA出现不希望的开环。快速稀释排除了酸不稳定官能团的不希望的分解。
• STABLE HELICAL IONIC POLYPEPTIDES
  申请人：Cheng Jianjun

  公开号：US20130274173A1

  公开（公告）日：2013-10-17

  The invention provides polymers comprising Formula I: wherein monomer is a repeating unit comprising 2, 3, 4, 5, 6 or 7 carbon atoms and the monomers are linked together through amide or ester bonds; n is about 6 to about 1000; and Linker is an optionally substituted carbon chain that is optionally interrupted by moieties such as oxygen, nitrogen, sulfur, phosphorus, or silicon. Charge is a moiety having a positive or negative charge on a heteroatom, such as nitrogen, oxygen, phosphorus, or sulfur; where the Linker separates the monomer and the Charge by at least six linear atoms. The invention also provides methods of preparing the polymers and the copolymers and methods of using the polymers and copolymers, for example, as drug delivery systems, as membrane penetrating peptides, and as therapeutic agents.

  本发明提供了具有以下式子（I）的聚合物：其中单体是由2、3、4、5、6或7个碳原子组成的重复单元，且单体通过酰胺或酯键连接在一起；n约为6到约1000；连接体是一种可以选择性地被氧、氮、硫、磷或硅等官能团中断的可选择性取代的碳链。电荷是具有异原子上的正或负电荷的官能团，例如氮、氧、磷或硫；其中连接体至少由六个线性原子将单体和电荷分开。本发明还提供了制备聚合物和共聚物的方法，以及使用聚合物和共聚物的方法，例如作为药物传递系统、作为膜穿透肽和作为治疗剂。
• Conformation switchable antimicrobial peptides and methods of using the same
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：US11225507B2

  公开（公告）日：2022-01-18

  The disclosure provides a class of pH-sensitive, helix/random conformation switchable antimicrobial polypeptide (HRS-AMP) compositions as a single agent to selectively kill bacteria (e.g., H. pylori) under acidic condition in the stomach with diminished bacterial resistance compared to currently used antibiotics. Methods of treating bacterial infections in the stomach are also provided.

  本公开提供了一类 pH 值敏感、螺旋/随机构象可转换的抗菌多肽（HRS-AMP）组合物，作为单剂在胃部酸性条件下选择性杀灭细菌（如幽门螺杆菌），与目前使用的抗生素相比，细菌耐药性降低。还提供了治疗胃部细菌感染的方法。
• CONFORMATION SWITCHABLE ANTIMICROBIAL PEPTIDES AND METHODS OF USING THE SAME
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：US20200399319A1

  公开（公告）日：2020-12-24

  The disclosure provides a class of pH-sensitive, helix/random conformation switchable antimicrobial polypeptide (HRS-AMP) compositions as a single agent to selectively kill bacteria (e.g., H. pylori ) under acidic condition in the stomach with diminished bacterial resistance compared to currently used antibiotics. Methods of treating bacterial infections in the stomach are also provided.
• US9243040B2
  申请人：——

  公开号：US9243040B2

  公开（公告）日：2016-01-26