(2S)-2-{3-[((1S)-1-carboxyethyl)oxycarbonyl]propanoyloxy}propanoic acid | 314069-32-4

• 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: (2S)-2-{3-[((1S)-1-carboxyethyl)oxycarbonyl]propanoyloxy}propanoic acid
• 英文别名: (2S)-2-[4-[(1S)-1-carboxyethoxy]-4-oxobutanoyl]oxypropanoic acid
• CAS: 314069-32-4
• 化学式: C₁₀H₁₄O₈
• 分子量: 262.216
• InChiKey: FEODHEMWPBPYNH-WDSKDSINSA-N

物化性质

• 熔点：
  59-61 °C
• 沸点：
  470.7±35.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S)-2-{3-[((1S)-1-carboxyethyl)oxycarbonyl]propanoyloxy}propanoic acid 、 (S)-(-)-乳酸苄酯 在 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以85%的产率得到bis[(2S)-1-oxo-1-[(2S)-1-oxo-1-phenylmethoxypropan-2-yl]oxypropan-2-yl] butanedioate
  参考文献：
  名称：

  Symmetrical biodegradable crosslinkers for use in polymeric devices

  摘要：

  There is a need for biodegradable hydrogels that deteriorate at defined rates under physiological conditions for use in engineered tissue constructs and drug delivery. These hydrogels should contain components that are readily synthesized, biocompatible and easily incorporated into hydrogel networks. This need was addressed through a judiciously designed series of crosslinkers composed of symmetrical oligo-glycolate and oligo-lactate esters terminated with vinylic moieties (1). These materials were incorporated into poly(HPMA) networks via free-radical polymerization. This work describes the preparation of symmetrical, lactate and glycolate ester based crosslinking agents and their incorporation into a hydrogel network composed of 2-hydroxypropyl methacrylamide (HPMA). By varying the number of lactic and glycolic acid residues (n = 0, 1, 2) within the crosslinker, the rate of hydrolytic degradation of the gel can be controlled. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.066
• 作为产物：
  描述：

  bis[(2S)-1-oxo-1-phenylmethoxypropan-2-yl] butanedioate 在 palladium on activated charcoal 氢气 作用下， 以 异丙醇 为溶剂， 25.0 ℃ 、344.74 kPa 条件下， 反应 5.0h， 以63%的产率得到(2S)-2-{3-[((1S)-1-carboxyethyl)oxycarbonyl]propanoyloxy}propanoic acid
  参考文献：
  名称：

  Symmetrical biodegradable crosslinkers for use in polymeric devices

  摘要：

  There is a need for biodegradable hydrogels that deteriorate at defined rates under physiological conditions for use in engineered tissue constructs and drug delivery. These hydrogels should contain components that are readily synthesized, biocompatible and easily incorporated into hydrogel networks. This need was addressed through a judiciously designed series of crosslinkers composed of symmetrical oligo-glycolate and oligo-lactate esters terminated with vinylic moieties (1). These materials were incorporated into poly(HPMA) networks via free-radical polymerization. This work describes the preparation of symmetrical, lactate and glycolate ester based crosslinking agents and their incorporation into a hydrogel network composed of 2-hydroxypropyl methacrylamide (HPMA). By varying the number of lactic and glycolic acid residues (n = 0, 1, 2) within the crosslinker, the rate of hydrolytic degradation of the gel can be controlled. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.066

文献信息

• Biodegradable cross-linkers having a polyacid connected to reactive groups for cross-linking polymer filaments
  申请人：Access Pharmaceuticals, Inc.

  公开号：US06521431B1

  公开（公告）日：2003-02-18

  Biodegradable cross-linkers are provided having a polyacid core with at least two acidic groups covalently connected to reactive groups usable to cross-link polymer filaments. Between at least one reactive group and an acidic group of the polyacid is a biodegradable region which preferably consists of a hydroxyalkyl acid ester sequence having 1, 2, 3, 4, 5 or 6 hydroxyalkyl acid ester groups. The polyacid may be attached to a water soluble region that is attached to the biodegradable region having attached reactive groups. The hydroxyalkyl acid ester group is preferably a lactate or glycolate. Polyacids include diacids, triacids, tetraacids and pentaacids, and the reactive group may contain a carbon-carbon double bond. A network of cross-linked polymer filaments having adefined biodegradation rate can be formed using the cross-linkers. The network may contain biologically active molecules, and can be in the form of a microparticle or nanoparticle, or hydrogel. The polymer filaments may be preformed polymer filaments of polynucleic acids, polypeptides, proteins or carbohydrates. The cross-linkers may be copolymerized with charged monomers such as acrylic monomers containing charged groups. Applications of the cross-linkers and network include controlled release of drugs and cosmetics, tissue engineering, wound healing, hazardous waste remediation, metal chelation, swellable devices for absorbing liquids and prevention of surgical adhesions.

  提供具有至少两个酸性基团的聚酸核心的可生物降解的交联剂，该核心与可用于交联聚合物纤维的反应性基团共价连接。在至少一个反应性基团和聚酸的酸性基团之间存在一个可生物降解的区域，该区域最好由具有1、2、3、4、5或6个羟烷酸酯基团的羟烷酸酯序列组成。聚酸可以连接到与附有反应性基团的可生物降解区域连接的水溶性区域。羟烷酸酯基团最好是乳酸或乙二醇酸酯。聚酸包括二酸、三酸、四酸和五酸，反应性基团可能含有碳-碳双键。可以使用这些交联剂形成具有定义的生物降解速率的交联聚合物纤维网络。该网络可以包含生物活性分子，并且可以采用微粒或纳米粒子，或者是水凝胶的形式。聚合物纤维可能是聚核酸、多肽、蛋白质或碳水化合物的预制聚合物纤维。这些交联剂可以与含带电基团的丙烯酸单体共聚合。交联剂和网络的应用包括药物和化妆品的控释、组织工程、伤口愈合、危险废物处理、金属螯合、吸收液体的膨胀设备以及预防手术粘连。
• Degradable cross-linking agents and cross-linked network polymers formed therewith
  申请人：——

  公开号：US20030078339A1

  公开（公告）日：2003-04-24

  Degradable cross-linkers which are used to form polymer networks which degrade under aqueous conditions are described. These cross-linkers comprise a central polyacid, monomeric or oligomeric degradable regions and an optional water soluble regions. These monomers are preferably polymerized using free radical or condensation polymerization. Degradation occurs at the ester linkages after cross-linking polymer filaments, and results in soluble polymer filaments which may be cleared from the body. Preferred applications of these materials include, for example, controlled release of drugs and cosmetics, tissue engineering, wound healing, hazardous waste remediation, metal chelation, swellable devices for absorbing liquids and the prevention of surgical adhesions.

  可降解交联剂可用于形成在水性条件下降解的聚合物网络。这些交联剂由中心聚酸、单体或低聚物可降解区以及任选的水溶性区组成。这些单体最好采用自由基聚合或缩合聚合。在交联聚合物丝后，酯连接处会发生降解，从而产生可从体内清除的可溶性聚合物丝。这些材料的首选应用包括药物和化妆品的控释、组织工程、伤口愈合、有害废物修复、金属螯合、吸收液体的可膨胀装置以及防止手术粘连等。
• Oligo-α-hydroxy Ester Cross-Linkers:  Impact of Cross-Linker Structure on Biodegradable Hydrogel Networks
  作者：Kenneth D. Eichenbaum、Allen A. Thomas、Gary M. Eichenbaum、Brian R. Gibney、David Needham、Patrick F. Kiser

  DOI：10.1021/ma0518306

  日期：2005.12.1

  We describe the synthesis of a series of biodegradable oligo-alpha-hydroxy ester cross-linkers and evaluate their impact on the degradation kinetics and macromolecule diffusion from a hydrogel network. By changing the steric and electronic environment at the site of degradation in the cross-linker, we were able to modulate the degradation, swelling kinetics, and corresponding release profiles of macromolecules from poly(HPMA) hydrogel networks under physiologically relevant conditions. As the steric hindrance and electron demand at the site of hydrolysis for three different cross-linkers was increased, the total time for the hydrogel network to completely dissolve increased from 2 to over 30 days while incubated in pH 7 buffer. As the number of hydrolyzable sites and the electron demand at the side of hydrolysis decreased, the time to completely dissolve decreased from weeks to several days. Increasing the cross-linking density for one of the degradable cross-linkers (1.5% to 3.0% feed ratio) increased the degradation time by several weeks. Burst release was absent for high molecular weight solutes because the release rate depended on controlled degradation of the polymer network and an increase in average network mesh size. The synthetically adaptable cross-linkers described herein offer a new approach for controlling the rate and extent of release from biodegradable hydrogel networks.
• US6521431B1
  申请人：——

  公开号：US6521431B1

  公开（公告）日：2003-02-18