2-Hydroxy-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

• 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: 2-Hydroxy-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) 2-hydroxypropanoate；(2,5-dioxopyrrolidin-1-yl) 2-hydroxypropanoate
• 化学式: C₇H₉NO₅
• 分子量: 187.152
• InChiKey: LSPGQBNTMPNPGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester 、 (S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid 在 碳酸氢钠 、 copper(II) sulfate 、 8-羟基喹啉 作用下， 以 丙酮 、 水 为溶剂， 反应 4.0h， 生成 N^α-lactoyl lysine
  参考文献：
  名称：

  A novel formation pathway of Nε-(carboxyethyl)lysine from lactic acid during high temperature exposure in wheat sourdough bread and chemical model

  摘要：

  DOI：

  10.1016/j.foodchem.2022.132942
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 乳酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 2-Hydroxy-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester
  参考文献：
  名称：

  Poly(ethylene glycol) (PEG)-lactic acid nanocarrier-based degradable hydrogels for restoring the vaginal microenvironment

  摘要：

  Women with bacterial vaginosis (BV) display reduced vaginal acidity, which make them susceptible to associated infections such as HIV. In the current study, poly(ethylene glycol) (PEG) nanocarrier-based degradable hydrogels were developed for the controlled release of lactic acid in the vagina of BV-infected women. PEG-lactic acid (PEG-LA) nanocarriers were prepared by covalently attaching lactic acid to 8-arm PEG-SH via cleavable thioester bonds. PEG-LA nanocarriers with 4 copies of lactic acid per molecule provided controlled release of lactic acid with a maximum release of 23% and 47% bound lactic acid in phosphate buffered saline (PBS, pH 7.4) and acetate buffer (AB, pH 4.3), respectively. The PEG nanocarrier-based hydrogels were formed by cross-linking the PEG-LA nanocarriers with 4-arm PEG-NHS via degradable thioester bonds. The nanocarrier-based hydrogels formed within 20 min under ambient conditions and exhibited an elastic modulus that was 100-fold higher than the viscous modulus. The nanocarrier-based degradable hydrogels provided controlled release of lactic acid for several hours; however, a maximum release of only 10%-14% bound lactic acid was observed possibly due to steric hindrance of the polymer chains in the cross-linked hydrogel. In contrast, hydrogels with passively entrapped lactic acid showed burst release with complete release within 30 min. Lactic acid showed antimicrobial activity against the primary BV pathogen Gardnerella vaginalis with a minimum inhibitory concentration (MIC) of 3.6 mg/ml. In addition, the hydrogels with passively entrapped lactic acid showed retained antimicrobial activity with complete inhibition G. vaginalis growth within 48 h. The results of the current study collectively demonstrate the potential of PEG nanocarrier-based hydrogels for vaginal administration of lactic acid for preventing and treating BV. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jconrel.2014.08.031

文献信息

• Poly(ethylene glycol) (PEG)-lactic acid nanocarrier-based degradable hydrogels for restoring the vaginal microenvironment
  作者：Sujata Sundara Rajan、Yevgeniy Turovskiy、Yashveer Singh、Michael L. Chikindas、Patrick J. Sinko

  DOI：10.1016/j.jconrel.2014.08.031

  日期：2014.11

  Women with bacterial vaginosis (BV) display reduced vaginal acidity, which make them susceptible to associated infections such as HIV. In the current study, poly(ethylene glycol) (PEG) nanocarrier-based degradable hydrogels were developed for the controlled release of lactic acid in the vagina of BV-infected women. PEG-lactic acid (PEG-LA) nanocarriers were prepared by covalently attaching lactic acid to 8-arm PEG-SH via cleavable thioester bonds. PEG-LA nanocarriers with 4 copies of lactic acid per molecule provided controlled release of lactic acid with a maximum release of 23% and 47% bound lactic acid in phosphate buffered saline (PBS, pH 7.4) and acetate buffer (AB, pH 4.3), respectively. The PEG nanocarrier-based hydrogels were formed by cross-linking the PEG-LA nanocarriers with 4-arm PEG-NHS via degradable thioester bonds. The nanocarrier-based hydrogels formed within 20 min under ambient conditions and exhibited an elastic modulus that was 100-fold higher than the viscous modulus. The nanocarrier-based degradable hydrogels provided controlled release of lactic acid for several hours; however, a maximum release of only 10%-14% bound lactic acid was observed possibly due to steric hindrance of the polymer chains in the cross-linked hydrogel. In contrast, hydrogels with passively entrapped lactic acid showed burst release with complete release within 30 min. Lactic acid showed antimicrobial activity against the primary BV pathogen Gardnerella vaginalis with a minimum inhibitory concentration (MIC) of 3.6 mg/ml. In addition, the hydrogels with passively entrapped lactic acid showed retained antimicrobial activity with complete inhibition G. vaginalis growth within 48 h. The results of the current study collectively demonstrate the potential of PEG nanocarrier-based hydrogels for vaginal administration of lactic acid for preventing and treating BV. (C) 2014 Elsevier B.V. All rights reserved.
• Polymer conjugates of ziconotide
  申请人：Nektar Therapeutics

  公开号：EP2898900B1

  公开（公告）日：2017-11-15
• Galectin 9-Polymer Conjugates
  申请人：Nishi Nozomu

  公开号：US20100009908A1

  公开（公告）日：2010-01-14

  Galectin 9, which is an immune function-controlling factor belonging to a new class that is different from known cytokines and is expected to be used as a therapeutic drug for various immune-related diseases such as an autoimmune disease, has disadvantages (such as high sensitivity to protease and poor solubility) to be solved in developing therapeutic drugs. Therefore, there is a need to overcome these disadvantages. Chemically modified galectin 9, prepared by conjugating a polymer (for example, poly(ethylene glycol: PEG) to galectin 9, in particular, stabilized galectin 9, is verified to exert higher solubility with improvements in pharmacodynamics and pharmacokinetics (for example, prolongation of action potential duration, such as prolongation of blood half-life and others) and in suppression of hemagglutination and thus has excellent characteristics as a drug.
• A novel formation pathway of Nε-(carboxyethyl)lysine from lactic acid during high temperature exposure in wheat sourdough bread and chemical model
  作者：Zhongfei Zhang、Weiwei Cheng、Xiaowen Wang、Mingfu Wang、Feng Chen、Ka-Wing Cheng

  DOI：10.1016/j.foodchem.2022.132942

  日期：2022.9