L-反式-吡咯烷-2,4-二羧酸 | 64769-66-0

• 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
• 中文名称: L-反式-吡咯烷-2,4-二羧酸
• 英文名称: (2S,4R)-L-proline-4-carboxylic acid
• 英文别名: L-Trans-pyrrolidine-2,4-dicarboxylic acid；trans-4-carboxy-L-proline；trans-2,4-PDC；PDC；(2S,4R)-pyrrolidine-2,4-dicarboxylic acid
• CAS: 64769-66-0
• 化学式: C₆H₉NO₄
• 分子量: 159.142
• InChiKey: NRSBQSJHFYZIPH-DMTCNVIQSA-N

物化性质

• 熔点：
  214-217oC
• 溶解度：
  可微溶于水
• 稳定性/保质期：
  在指定条件下稳定，远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  存放在密封容器内，并置于阴凉、干燥处。

制备方法与用途

反式-4-羧基-L-脯氨酸是一种选择性谷氨酸转运体抑制剂。

反应信息

• 作为产物：
  描述：

  L-羟基脯氨酸 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 jones reagent 、 氢气 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 二甲基亚砜 、 丙酮 、 甲苯 为溶剂， -5.0~80.0 ℃ 、344.73 kPa 条件下， 反应 342.67h， 生成 L-反式-吡咯烷-2,4-二羧酸
  参考文献：
  名称：

  Conformationally defined neurotransmitter analogs. Selective inhibition of glutamate uptake by one pyrrolidine-2,4-dicarboxylate diastereomer

  摘要：

  In order to determine the conformational requirements for binding of L-glutamate to the proteins involved in the process of neurotransmission, rigid analogues containing an embedded glutamate moiety have been prepared. These ''conformer mimics'', the pyrrolidine-2,4-dicarboxylates 4, 7, 11, and 14, were synthesized from commercially available trans-4-hydroxy-L-proline and cis-4-hydroxy-D-proline, and then were tested for their ability to inhibit the high-affinity transport of [H-3]-L-glutamate into synaptosomes and to block the binding of radioligands to the NMDA (N-methyl-D-aspartate), KA (kainate), and QA (quisqualate) glutamate neurotransmitter receptor sites. While none of the four analogues binds effectively to the excitatory receptors, the L-trans-isomer 7 is a potent and selective competitive inhibitor of L-glutamate transport. These results delineate a specific structural/conformational preference for binding to the uptake system that is distinct from that required for binding to the NMDA, KA, and QA receptors.

  DOI：

  10.1021/jm00106a037

文献信息

• 3-alkylaryl aspartate compounds and their use for selective enhancement of synaptic transmission
  申请人：Esslinger S. Christopher

  公开号：US20070142467A1

  公开（公告）日：2007-06-21

  The present invention provides an L-aspartate derivative compound represented by the following structure wherein Ar represents an aromatic group; L represents a linking moiety; R represents hydrogen, alkyl, aryl, or heteroaryl; and indicates that the stereochemistry at the 3-position can be R or S. The compounds of the invention are useful for selectively inhibiting EAAT3 and for enhancing synaptic transmission. Additionally, the inventive compounds can be used to treat a patient suffering from Alzheimers disease or a neuropathy or a neurodegenerative disease in which L-glutamate transporter activity is involved in the onset of the disease.

  本发明提供了一种由以下结构表示的L-天冬氨酸衍生物化合物 其中Ar代表芳香基团；L代表连接基团；R代表氢、烷基、芳基或杂环芳基；和 表示3位的立体化学可以是R或S。本发明的化合物对选择性抑制EAAT3和增强突触传递具有用处。此外，这些创新性化合物可用于治疗患有阿尔茨海默病或神经病或神经退行性疾病的患者，其中L-谷氨酸转运蛋白活性参与了疾病的发病。
• An enantioselective route to pyrrolidines: Removal of the chiral template from homochiral pyrroloimidazoles
  作者：Raymond CF Jones、Kevin J Howard、John S Snaith

  DOI：10.1016/0040-4039(96)00114-1

  日期：1996.3

  Two-step reductive removal of the chiral template from optically active pyrroloimidazoles, available from 1,3-dipolar cycloaddition of homochiral imidazolinium ylides, gives optically active substituted pyrrolidines. Selective manipulation of the substituents affords, e.g. naturally occurring proline derivatives and homochiral pyrrolizidines.

  从旋光性吡咯并咪唑类化合物中进行两步还原性去除，可以从同手性咪唑啉鎓基化物的1，3-偶极环加成中获得旋光性取代的吡咯烷类。取代基的选择性操纵提供了例如天然存在的脯氨酸衍生物和同手性吡咯并核苷。
• COSMETIC OR DERMATOLOGICAL COMPOSITION COMPRISING A POLYMER BEARING JUNCTION GROUPS, AND COSMETIC TREATMENT PROCESS
  申请人：Chodorowski-Kimmes Sandrine

  公开号：US20100239509A1

  公开（公告）日：2010-09-23

  The present patent application relates to a cosmetic or dermatological composition comprising, in a cosmetically or dermatologically acceptable medium, a polymer comprising: (a) a polymer backbone that may be obtained by reaction: of a polyol comprising 3 to 6 hydroxyl groups; of a monocarboxylic acid containing 6 to 32 carbon atoms; of a polycarboxylic acid comprising at least two carboxylic groups COOH, and/or of a cyclic anhydride such as a polycarboxylic acid and/or of a lactone comprising at least one carboxylic group COOH; and (b) at least one junction group linked to the said polymer backbone and capable of establishing H bonds with one or more partner junction groups, each pairing of a junction group involving at least three H (hydrogen) bonds. The patent application also concerns a cosmetic treatment process using the said composition.

  本专利申请涉及一种化妆品或皮肤科学组合物，包括在化妆品或皮肤科学上可接受的介质中，包含以下聚合物的组合物：(a) 由以下反应得到的聚合物骨架：含有3至6个羟基的多元醇；含有6至32个碳原子的一元羧酸；至少含有两个羧基COOH的多元羧酸，和/或类似多元羧酸的环酐和/或至少含有一个羧基COOH的内酯；以及(b) 至少一个连接到所述聚合物骨架的连接基团，并能够与一个或多个配对连接基团建立H键，每个连接基团的配对涉及至少三个H（氢）键。该专利申请还涉及使用所述组合物的化妆品处理过程。
• COMPOSITION COMPRISING A POLYCONDENSATE, METHOD OF TREATMENT, POLYCONDENSATE, AND METHOD OF PREPARATION
  申请人：GIUSTINIANI Pascal

  公开号：US20090028807A1

  公开（公告）日：2009-01-29

  The present application relates to a cosmetic or pharmaceutical, in particular lipstick, composition comprising a polycondensate The application also relates to a method of cosmetic treatment using the composition, the polycondensate thus defined and a method of preparing the polycondensate.

  本申请涉及一种化妆品或药用品，特别是口红，包括聚缩酸酯的组合物。该申请还涉及一种使用该组合物进行化妆处理的方法，所述聚缩酸酯的定义以及一种制备聚缩酸酯的方法。
• COSMETIC OR PHARMACEUTICAL COMPOSITION COMPRISING A POLYCONDENSATE, THE SAID POLYCONDENSATE AND METHOD OF COSMETIC TREATMENT
  申请人：Malle Gerard

  公开号：US20100272660A1

  公开（公告）日：2010-10-28

  The present application relates to a cosmetic or pharmaceutical composition comprising a polycondensate capable of being obtained by the reaction of the following monomers alone: of 10 to 30% by weight, relative to the total weight of the polycondensate, of one or more polyols comprising 3 to 6 hydroxyl groups; of 30 to 80% by weight, relative to the total weight of the polycondensate, of one or more linear, branched and/or cyclic, saturated or unsaturated, non-aromatic monocarboxylic acids comprising 6 to 32 carbon atoms; of 1 to 40% by weight, relative to the total weight of the polycondensate, of one or more polycarboxylic acids and/or cyclic anhydrides of such a polycarboxylic acid and/or lactones comprising at least one COOH group; and optionally of 0.1 to 15% by weight, relative to the total weight of the polycondensate, of one or more silicones having a hydroxyl and/or carboxyl functional group. The application also relates to a method of cosmetic treatment using the said composition, and the polycondensate thus defined.

  本申请涉及一种化妆品或药用组合物，包括由以下单体反应而得的聚缩酸酯：相对于聚缩酸酯的总重量，占10至30%的一种或多种含有3至6个羟基的多元醇；占30至80%的一种或多种线性、支链和/或环状、饱和或不饱和、非芳香族的单羧酸，含有6至32个碳原子；占聚缩酸酯总重量的1至40%的一种或多种多羧酸和/或多羧酸的环状酐和/或含有至少一个COOH基团的内酯；以及可选地占聚缩酸酯总重量的0.1至15%的一种或多种硅氧烷，具有羟基和/或羧基官能团。该申请还涉及使用所述组合物进行化妆处理的方法，以及如此定义的聚缩酸酯。