cis-4-carboxy-D-proline dimethyl ester | 64750-03-4

• 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: cis-4-carboxy-D-proline dimethyl ester
• 英文别名: dimethyl (2R,4R)-pyrrolidine-2,4-dicarboxylate
• CAS: 64750-03-4
• 化学式: C₈H₁₃NO₄
• 分子量: 187.196
• InChiKey: CBIVLMXMLNQQLA-PHDIDXHHSA-N

物化性质

• 沸点：
  258.6±40.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-4-carboxy-D-proline dimethyl ester 在 三乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 生成 (2R,4R)-1-((4E,6E)-(2S,3S,8S,9S)-3-Acetylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoyl)-pyrrolidine-2,4-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  仅由Adda和一个其他氨基酸组成的微囊藻毒素类似物作为PP1 / PP2A抑制剂具有中等活性。

  摘要：

  一系列大大简化的微囊藻毒素类似物，仅由Adda（微囊藻毒素，结节蛋白和motuporin共有的β-氨基酸）组成，并合成了一个单独的氨基酸残基，并筛选了抑制蛋白磷酸酶1和2A的蛋白。几种类似物显示为酶的中纳摩尔抑制剂。

  DOI：

  10.1016/s0960-894x(03)00588-2
• 作为产物：
  描述：

  N-(benzyloxycarbonyl)-cis-4-carboxy-D-proline dimethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 cis-4-carboxy-D-proline dimethyl ester
  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

• METHOD OF INHIBITING THE TRANSPORT OF L-GLUTAMATE
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP0497895A1

  公开（公告）日：1992-08-12
• US5942537A
  申请人：——

  公开号：US5942537A

  公开（公告）日：1999-08-24
• [EN] METHOD OF INHIBITING THE TRANSPORT OF L-GLUTAMATE
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：WO1991006536A1

  公开（公告）日：1991-05-16

  (EN) A method of inhibiting the transport of a neurotransmitter away from the synapse comprising contacting a neurotransmitter transporter with a compound having structure (I), wherein R1 = CO2H; -P(OH2); -SO3H; CO2R3; P(OR3)2; -SO3R; (a); or CONHR3 in any combination and wherein R2 = OR3, NR32, alkyl, or substituted alkyl and R3 = alkyl or substituted alkyl.(FR) Procédé d'inhibition du transport d'un neurotransmetteur en l'éloignant de la synapse, et consistant à mettre en contact un transporteur du neurotransmetteur avec un composé ayant la structure (I) dans laquelle R1 représente CO2H; -P(OH2); -SO3H; CO2R3; P(OR3)2; -SO3R; (a); ou CONHR3 dans n'importe quelle combinaison, et dans laquelle R2 représente OR3, NR32, alkyl, ou alkyl substitué et R3 représente alkyl ou alkyl substitué.
• Conformationally defined neurotransmitter analogs. Selective inhibition of glutamate uptake by one pyrrolidine-2,4-dicarboxylate diastereomer
  作者：Richard J. Bridges、Mark S. Stanley、Michael W. Anderson、Carl W. Cotman、A. Richard Chamberlin

  DOI：10.1021/jm00106a037

  日期：1991.2

  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.
• Microcystin analogues comprised only of adda and a single additional amino acid retain moderate activity as PP1/PP2A inhibitors
  作者：Brian M Gulledge、James B Aggen、Hugo Eng、Khuloud Sweimeh、A.Richard Chamberlin

  DOI：10.1016/s0960-894x(03)00588-2

  日期：2003.9

  A series of greatly simplified microcystin analogues comprised only of Adda (the beta-amino acid common to the microcystins, nodularins, and motuporin,) and a single additional amino acid residue was synthesized and screened for inhibition of the protein phosphatases 1 and 2A. Several of the analogues were shown to be mid-nanomolar inhibitors of the enzymes.

  一系列大大简化的微囊藻毒素类似物，仅由Adda（微囊藻毒素，结节蛋白和motuporin共有的β-氨基酸）组成，并合成了一个单独的氨基酸残基，并筛选了抑制蛋白磷酸酶1和2A的蛋白。几种类似物显示为酶的中纳摩尔抑制剂。