sarcosine N-thiocarboxyanhydride | 59857-31-7

• 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: sarcosine N-thiocarboxyanhydride
• 英文别名: 3-methyl-1,3-thiazolidine-2,5-dione
• CAS: 59857-31-7
• 化学式: C₄H₅NO₂S
• 分子量: 131.155
• InChiKey: AIFQYAOYRPTSID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(ethoxycarbonothioyl)-N-methylglycine 在 三溴化磷 作用下， 生成 sarcosine N-thiocarboxyanhydride
  参考文献：
  名称：

  Poly(ε-caprolactone)-block-polysarcosine by Ring-Opening Polymerization of Sarcosine N-Thiocarboxyanhydride: Synthesis and Thermoresponsive Self-Assembly

  摘要：

  利用氧胺端 PCL 引发的肌氨酸 N-硫代羧基酸酐开环聚合反应，合成了由聚肌氨酸（PSar）和聚(ε-己内酯)（PCL）组成的生物相容性两亲嵌段共聚物，并通过核磁共振、SEC 和 DSC 对其进行了表征。利用薄膜水合和纳米沉淀技术，详细研究了两种三嵌段共聚物 PSar8-b-PCL28-b-PSar8 （CS7）和 PSar16-b-PCL40-b-PSar16 （CS10）在稀溶液中自组装形成聚合物组的情况。通过对两种共聚物进行薄膜水合，获得了一些巨型囊泡，并通过激光共聚焦扫描显微镜进行了观察。在室温下通过纳米沉淀法获得了单层薄片和纳米纤维（厚度或直径为 8-10 nm），并通过冷冻电镜进行了观察。这些薄片和纤维结构在加热至 65 ℃（>Tm,PCL）后转变为蠕虫状圆柱体和球体（D ∼ 30-100 nm）。将 CS10 悬浮液加热至 90 °C，最终形成多胶束聚合体（D ∼ 100-500 nm）。聚合体的形成机制二是胶束通过水的扩散和亲水核的形成扩展成囊泡。细胞存活率测试证实自组装体没有细胞毒性。

  DOI：

  10.1021/acs.biomac.5b00930

文献信息

• Poly(ε-caprolactone)-<i>block</i>-polysarcosine by Ring-Opening Polymerization of Sarcosine <i>N</i>-Thiocarboxyanhydride: Synthesis and Thermoresponsive Self-Assembly
  作者：Yangwei Deng、Tao Zou、Xinfeng Tao、Vincent Semetey、Sylvain Trepout、Sergio Marco、Jun Ling、Min-Hui Li

  DOI：10.1021/acs.biomac.5b00930

  日期：2015.10.12

  Biocompatible amphiphilic block copolymers composed of polysarcosine (PSar) and poly(ε-caprolactone) (PCL) were synthesized using ring-opening polymerization of sarcosine N-thiocarboxyanhydride initiated by oxyamine-ended PCL and characterized by NMR, SEC, and DSC. Self-assembling of two triblock copolymers PSar8-b-PCL28-b-PSar8 (CS7) and PSar16-b-PCL40-b-PSar16 (CS10) in dilute solution was studied in detail toward polymersome formation using thin-film hydration and nanoprecipitation techniques. A few giant vesicles were obtained by thin-film hydration from both copolymers and visualized by confocal laser scanning microscope. Unilamellar sheets and nanofibers (with 8–10 nm thickness or diameter) were obtained by nanoprecipitation at room temperature and observed by Cryo-TEM. These lamellae and fibrous structures were transformed into worm-like cylinders and spheres (D ∼ 30–100 nm) after heating to 65 °C (>Tm,PCL). Heating CS10 suspensions to 90 °C led eventually to multilamellar polymersomes (D ∼ 100–500 nm). Mechanism II, where micelles expand to vesicles through water diffusion and hydrophilic core forming, was proposed for polymersome formation. A cell viability test confirmed the self-assemblies were not cytotoxic.

  利用氧胺端 PCL 引发的肌氨酸 N-硫代羧基酸酐开环聚合反应，合成了由聚肌氨酸（PSar）和聚(ε-己内酯)（PCL）组成的生物相容性两亲嵌段共聚物，并通过核磁共振、SEC 和 DSC 对其进行了表征。利用薄膜水合和纳米沉淀技术，详细研究了两种三嵌段共聚物 PSar8-b-PCL28-b-PSar8 （CS7）和 PSar16-b-PCL40-b-PSar16 （CS10）在稀溶液中自组装形成聚合物组的情况。通过对两种共聚物进行薄膜水合，获得了一些巨型囊泡，并通过激光共聚焦扫描显微镜进行了观察。在室温下通过纳米沉淀法获得了单层薄片和纳米纤维（厚度或直径为 8-10 nm），并通过冷冻电镜进行了观察。这些薄片和纤维结构在加热至 65 ℃（>Tm,PCL）后转变为蠕虫状圆柱体和球体（D ∼ 30-100 nm）。将 CS10 悬浮液加热至 90 °C，最终形成多胶束聚合体（D ∼ 100-500 nm）。聚合体的形成机制二是胶束通过水的扩散和亲水核的形成扩展成囊泡。细胞存活率测试证实自组装体没有细胞毒性。
• Therapeutic Delivery of H₂S via COS: Small Molecule and Polymeric Donors with Benign Byproducts
  作者：Chadwick R. Powell、Jeffrey C. Foster、Benjamin Okyere、Michelle H. Theus、John B. Matson

  DOI：10.1021/jacs.6b07204

  日期：2016.10.19

  Carbonyl sulfide (COS) is a gas that may play important roles in mammalian and bacterial biology, but its study is limited by a lack of suitable donor molecules. We report here the use of N-thiocarboxyanhydrides (NTAs) as COS donors that release the gas in a sustained manner under biologically relevant conditions with innocuous peptide byproducts. Carbonic anhydrase converts COS into H2S, allowing NTAs to serve as either COS or H2S donors, depending on the availability of the enzyme. Analysis of the pseudo-first-order H2S release rate under biologically relevant conditions revealed a release half-life of 75 min for the small molecule NTA under investigation. A polynorbornene bearing pendant NTAs made by ring-opening metathesis polymerization was also synthesized to generate a polymeric COS/H2S donor. A half-life of 280 min was measured for the polymeric donor. Endothelial cell proliferation studies revealed an enhanced rate of proliferation for cells treated with the NTA over untreated controls.
• Controlled Polymerization of N-Substituted Glycine <i>N</i>-Thiocarboxyanhydrides Initiated by Rare Earth Borohydrides toward Hydrophilic and Hydrophobic Polypeptoids
  作者：Xinfeng Tao、Yangwei Deng、Zhiquan Shen、Jun Ling

  DOI：10.1021/ma501131t

  日期：2014.9.23

  N-substituted glycine N-thiocarboxyanhydrides (NTAs) are alternative monomers to prepare polypeptoids with large-scale producing potential compared to the corresponding N-carboxyanhydrides (NCAs) due to their easily synthetic approach and stability during purification and storage. Novel monomer N-butylglycine NTA (NBG-NTA) has been synthesized and well characterized for the first time. Rare earth borohydrides [RE(BH4)(3)(THF)(3), RE = Sc, Y, La, Nd, Dy, and Lit] have been first applied in the polymerization of sarcosine NTA (Sar-NTA) and NBG-NTA to achieve high molecular weight (MW) hydrophilic and hydrophobic polypeptoids. Polysarcosines (PSars), poly(N-butylglycine)s (PNBGs), and their copolymers with high yields, high MWs, and moderate MW distributions are synthesized at 60 degrees by using RE(BH4)(3)(THF)(3) initiators. MWs of polypeptoids are controlled by feed molar ratios. For instance, PSar with an absolute M-n, of 27.7 kDa (DP = 390) and PDI of 1.14 is produced successfully from Sar-NTA. Thermoresponsive random copolypeptoids poly(sarcosine-r-N-butylglycine)s [P(Sar-r-NBG)s] have reversible phase transitions (cloud point temperature) in aqueous solution and minimal cytotoxicity comparable to PEG and PSar, which is promising in various biomedical and biotechnological applications. Thermal properties of homo- and co-polypeptoids are investigated by TGA and DSC measurements.
• Polymersomes with aggregation-induced emission based on amphiphilic block copolypeptoids
  作者：Xinfeng Tao、Hui Chen、Sylvain Trépout、Jiayu Cen、Jun Ling、Min-Hui Li

  DOI：10.1039/c9cc07501a

  日期：——

  Fluorescent and biocompatible polymersomes based on the amphiphilic block copolypeptoid P(TPE-NAG)-b-PSar are promising for bio-imaging and drug delivery applications.

  基于两性块状共聚肽P(TPE-NAG)-b-PSar的荧光和生物相容性聚合物囊泡对生物成像和药物传递应用具有很大潜力。

表征谱图