5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid | 32999-84-1

• 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: 5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid
• 英文别名: N-benzoyl-N',N'-dipropyl-S-(+)-isoglutamine；(S)-proglumide；L-proglumide；(4S)-4-benzamido-5-(dipropylamino)-5-oxopentanoic acid
• CAS: 32999-84-1
• 化学式: C₁₈H₂₆N₂O₄
• 分子量: 334.415
• InChiKey: DGMKFQYCZXERLX-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  86.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid 、 5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid 、 乙醇 生成 丙谷胺
  参考文献：
  名称：

  IUCHI, KOJI;ITO, KEIZO;TSUKAMOTO, GORO, CHEM. AND PHARM. BULL., 36,(1988) N 9, C. 3433-3438

  摘要：

  DOI：
• 作为产物：
  描述：

  Z-Glu-NPr2 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 6.0h， 生成 5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid
  参考文献：
  名称：

  Synthesis and effect on gastric secretion of several di-or tripeptides related to proglumide.

  摘要：

  与普洛古米德（PhCO-DL-Glu-NPr2）相关的几种N-酰二肽或三肽被制备，并通过腹腔注射在大鼠身上检查其对胃分泌的影响。PhCOGlu（Phe-NH2）-NPr2、Z-Glu（Phe-NH2）-NPr2、PhCO-Glu（NPr2）-Phe-NH2和PhCO-Asp-(Phe-NH2)-NPr2抑制胃分泌，而PhCO-Glu（Asp-Phe-NH2）-NPr2则刺激胃分泌。在这些肽中，PhCO-Glu（Phe-NH2）-NPr2对胃分泌表现出最强的抑制活性，其效力超过普洛古米德。

  DOI：

  10.1248/cpb.36.3961

文献信息

• Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase
  作者：Garrett Hellinghausen、Diego A. Lopez、Jauh T. Lee、Yadi Wang、Choyce A. Weatherly、Abiud E. Portillo、Alain Berthod、Daniel W. Armstrong

  DOI：10.1002/chir.22985

  日期：2018.9

  macrocyclic glycopeptide‐based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide‐based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide‐based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary

  通过对万古霉素的Edman降解制备的修饰的基于大环糖肽的手性固定相（CSP）被首次评估为手性选择剂。将其适用性与其他基于大环糖肽的CSP（TeicoShell和VancoShell）进行了比较。此外，还进一步检查了另一种基于大环糖肽的修饰CSP NicoShell。最初的评估集中在与这些糖肽的互补行为上。根据以前的工作，使用了一种筛选方法，用于对50种手性化合物的对映体分离，其中包括氨基酸，农药，兴奋剂和多种药物。使用表面多孔（核-壳）颗粒载体可实现快速有效的手性分离。总体，万古霉素埃德曼降解产物（EDP）与TeicoShell类似，在极性离子模式下对酸性化合物具有高对映选择性。使用液相色谱-质谱联用EDP同时分离5种外消旋脯氨酸的对映异构体，时间约为3分钟。其他亮点包括同时用VancoShell液相色谱分离rac-amphetamine和rac-methamphetamine，用Nico
• Application of Cyclam-Capped β-Cyclodextrin-Bonded Silica Particles as a Chiral Stationary Phase in Capillary Electrochromatography for Enantiomeric Separations
  作者：Yinhan Gong、Hian Kee Lee

  DOI：10.1021/ac0204909

  日期：2003.3.1

  Two novel types of substituted cyclam-capped β-cyclodextrin (β-CD)-bonded silica particles have been prepared and used as chiral stationary phases in capillary electrochromatography (CEC). The two stationary phases have a chiral selector with three recognition sites:  β-CD, cyclam, and the latter's sidearm. They exhibit excellent enantioselectivities in CEC for a wide range of compounds as a result of the cooperative functioning of the anchored β-CD and cyclam. After inclusion of the metal ion (Ni2+) from the running buffer into the substituted cyclams and their sidearm ligands, the bonded stationary phases become positively charged and can provide extra electrostatic interactions with ionizable solutes and enhance the dipolar interactions with some polar neutral solutes. This enhances the host−guest interaction with some solutes and improves chiral recognition and enantioselectivity. These new types of stationary phases exhibit great potential for fast chiral separations in CEC.

  两种新型取代的环烷基顶端β-环糊精（β-CD）键合二氧化硅颗粒已被制备并用于毛细管电色谱（CEC）中的手性固定相。这两种固定相具有一个包含三个识别位点的手性选择剂：β-CD、环烷基和环烷基的侧链。它们在CEC中对广泛化合物表现出优异的对映选择性，原因在于锚定的β-CD和环烷基的协同作用。在运行缓冲液中金属离子（Ni2+）被包含到取代的环烷基及其侧链配体后，键合的固定相变为正电荷，从而能够与可电离溶质提供额外的静电相互作用，并增强与一些极性中性溶质的偶极相互作用。这增强了与某些溶质的宿主-客体相互作用，提高了手性识别和对映选择性。这些新型固定相在CEC中展现出快速手性分离的巨大潜力。
• Synthesis of N-acyl-.GAMMA.-D-glutamyl peptide derivatives containing a C-terminal small fragment of cholecystokinin and their effects on gastric secretion.
  作者：KOJI IUCHI、KEIZO ITO、GORO TSUKAMOTO

  DOI：10.1248/cpb.36.3433

  日期：——

  N-Acyl-γ-D-glutamyl peptide derivatives containing a C-terminal small fragment of cholecystokinin were prepared and their effects on gastric secretion were investigated. PhCO-D-Glu(Phe-NH2)-NPr2 and PhCO-D-Glu(Asp-Phe-NH2)-NPr2 inhibited gastric secretion, while PhCO-D-Glu(Met-Asp-Phe-NH2)-NPr2 and PhCO-D-Glu(Trp-Met-Asp-Phe-NH2)-NPr2 stimulated gastric secretion. The substitution of the acyl function at the N-terminal of PhCO-D-Glu(Phe-NH2)-NPr2 affected the activity. Z-D-Glu(Phe-NH2)-NPr2, 4-chlorobenzoyl-D-Glu-(Phe-NH2)-NPr2 and isonicotinoyl-D-Glu(Phe-NH2)-NPr2 were found to have more potent inhibitory activity against gastric secretion than proglumide (PhCO-DL-Glu-NPr2).

  制备了含有胆囊收缩素 C 端小片段的 N-酰基-γ-D-谷氨酰肽衍生物，并研究了它们对胃液分泌的影响。PhCO-D-Glu(Phe-NH2)-NPr2和PhCO-D-Glu(Asp-Phe-NH2)-NPr2抑制胃液分泌，而PhCO-D-Glu(Met-Asp-Phe-NH2)-NPr2和PhCO-D-Glu(Trp-Met-Asp-Phe-NH2)-NPr2刺激胃液分泌。PhCO-D-Glu(Phe-NH2)-NPr2 N 端酰基功能的替代影响了其活性。研究发现，Z-D-Glu(Phe-NH2)-NPr2、4-氯苯甲酰基-D-Glu-(Phe-NH2)-NPr2 和异烟酰基-D-Glu(Phe-NH2)-NPr2 对胃液分泌的抑制活性比丙谷胺（PhCO-DL-Glu-NPr2）更强。
• 一种手性丙谷胺的制备方法与药用组合物
  申请人：成都译山生物科技有限公司

  公开号：CN106220529B

  公开（公告）日：2017-12-08

  本发明提供了一种手性丙谷胺的制备方法，还提供了手性丙谷胺在制备治疗和/或预防消化道溃疡的一种药物组合物。本发明采用一种原材料易得、工序少、能耗低、操作简便、环保安全的制备方法，得到了光学纯度高、收率高、成本低的手性丙谷胺，非常适合产业上的应用；而且，与消旋丙谷胺相比，在对溃疡相同或相当治疗效果的情况下，本发明正旋5‑(R)‑二丙基氨基‑4‑苯甲酰氨基‑5‑氧代‑戊酸可以大幅度的降低给药剂量，减轻了给药时肌体代谢的负担，有效的消除了因消旋丙谷胺是混合物而可能带来的安全隐患问题，进一步保障了病患的用药安全。
• Resolution of ( RS )-Proglumide using Lipase from Candida cylindraceae
  作者：R.V Muralidhar、R.R Chirumamilla、V.N Ramachandran、R Marchant、P Nigam

  DOI：10.1016/s0968-0896(01)00409-6

  日期：2002.5

  Proglumide is used in the treatment of neuropathic pain. It acts by inhibiting peptide cholecystokinin (CCK). Neural injury produces an elevation in plasma CCK. Proglumide has been also shown to augment the analgesic effect of sustained release morphine in neuropathic pain. Currently proglumide is administered as a racemic mixture. In the present study, an attempt is made to separate the racemic Mixture of the drug using lipase obtained from Candida cylindracea by stereoselective esterification. Enzymatic stereoselective esterification was carried out in organic solvents. The resolution was studied using a chromatographic column with a chiral support and mass spectrometry. The reaction conditions for stereoselective esterification including amount of substrate, amount of enzyme. alcohol, solvent and temperature were optimised during the present investigation. Butanol and hexanol were found to be suitable for formation of S and R esters. respectively. Hexane was the best solvent for esterification and the optimum temperature was found to be 30 degreesC. (C) 2002 Elsevier Science Ltd. All rights reserved.