L-glutamic acid 5-isopropyl ester | 16652-44-1

• 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: L-glutamic acid 5-isopropyl ester
• 英文别名: L-Glutaminsaeure-γ-isopropylester；(2S)-2-amino-5-oxo-5-propan-2-yloxypentanoic acid
• CAS: 16652-44-1
• 化学式: C₈H₁₅NO₄
• 分子量: 189.211
• InChiKey: FDVPMGQVGDSDOY-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  L-glutamic acid 5-isopropyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 、 N,N-二异丙基乙胺 、 chlorotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 3-{(S)-2-[3-((S)-2-tert-Butoxycarbonylamino-4-isopropoxycarbonyl-butyrylamino)-benzoylamino]-4-isopropoxycarbonyl-butyrylamino}-benzoic acid benzyl ester
  参考文献：
  名称：

  Large Increase in Cation Binding Affinity of Artificial Cyclopeptide Receptors by an Allosteric Effect

  摘要：

  The receptor properties of a cyclopeptide composed of L-glutamic acid and 3-aminobenzoic acid in an alternating sequence are described. H-1 NMR, NOESY Nh LR. and FT-IR spectroscopic investigations show that this cyclic peptide is relatively flexible in solution. Still, it is able to bind cations by cation-pi interactions. For the n-butyltrimethylammonium iodide complex, for example, an association constant of 300 M-1 has been determined in chloroform Besides cations, the cyclopeptide is also able to bind certain anions, such as sulfonates or phosphonates, at a second binding site. Nh IR and FT-IR spectroscopic investigations show that these anions are hydrogen bonded to the peptidic NH groups. Anion complexation results in an increase of the cyclic peptide's cation affinity by a factor of 10(3)-10(4). The cyclopeptide-tosylate complex structure in solution was assigned by FT-IR, H-1 NMR, and NOESY NMR spectroscopic methods as well as molecular modeling, This structure shows that the drastic increase in cation binding affinity can be correlated with a preorganization of the cyclic peptide by the anion as well as electrostatic interactions between anion and cationic substrates in the final complex. Therefore, the influence of the anions on the complexing behavior of the cyclopeptide can be regarded as an allosteric effect. Association constants of the K+-18-crown-6, Na+-15-crown-5, and n-butyltrimethylammonium cation complexes have been determined by dilution and competitive NMR titrations.

  DOI：

  10.1021/ja983970j
• 作为产物：
  描述：

  在 platinum on carbon 、 氢气 、 溶剂黄146 作用下， 以 水 、 乙酸乙酯 为溶剂， 以96 %的产率得到L-glutamic acid 5-isopropyl ester
  参考文献：
  名称：

  [EN] METHOD FOR PREVENTING INSECT DAMAGE TO PLANTS
  [FR] PROCÉDÉ DE LUTTE CONTRE LES DOMMAGES CAUSÉS PAR LES INSECTES SUR LES VÉGÉTAUX
  [JA] 植物の虫害を防止する方法

  摘要：

  植物の虫害を防止する技術等の農園芸分野における有用な技術を提供する。各種グルタミン酸誘導体を利用することにより植物の虫害を防止する。

  公开号：

  WO2024010005A1

文献信息

• Use of Anhydrous Hydrogen Fluoride in Peptide Synthesis. I. Behavior of Various Protective Groups in Anhydrous Hydrogen Fluoride
  作者：Shumpei Sakakibara、Yasutsugu Shimonishi、Yasuo Kishida、Masanori Okada、Hideo Sugihara

  DOI：10.1246/bcsj.40.2164

  日期：1967.9

  properties of anhydrous hydrogen fluoride (HF) as a reagent for the acidolysis of various protective groups have been studied. Amino acids with various protective groups were each treated with HF at 0 or 20°C in the presence of anisole, and the reaction products were tested. Thus, HF was found to be much better than the other known reagents, such as hydrogen bromide and trifluoroacetic acid. In the present

  已经研究了无水氟化氢 (HF) 作为酸解各种保护基团的试剂的性质。在苯甲醚存在下，在 0 或 20°C 下用 HF 分别处理具有各种保护基团的氨基酸，并测试反应产物。因此，发现 HF 比其他已知试剂（例如溴化氢和三氟乙酸）好得多。在本研究中，以下基团首次被证明可以安全去除：硝基精氨酸中的硝基、二苯甲酰胺中的二苯甲基、叔丁基半胱氨酸中的叔丁基、异丙氧基羰基和异丙基酯基团。设计了一种新的方便的装置，用于安全处理用于肽合成的 HF。
• Cosmestic composition
  申请人：UNILEVER PLC

  公开号：EP0572167A1

  公开（公告）日：1993-12-01

  A composition suitable for topical application to mammalian skin and hair for inducing, maintaining or increasing hair growth comprises a hair growth promoter chosen from glutamic acid derivatives and salts thereof. The composition preferably also comprises an activity enhancer which may be chosen from hair growth stimulants, penetration enhancers and cationic polymers.

  一种适用于哺乳动物皮肤和毛发的外用组合物，可诱导、维持或增加毛发生长，其中包括一种毛发生长促进剂，选自谷氨酸衍生物及其盐类。该组合物最好还包含一种活性增强剂，它可以选自毛发生长刺激剂、渗透增强剂和阳离子聚合物。
• PROCESS FOR PRODUCING N-PROTECTED AMINO ACID
  申请人：Kaneka Corporation

  公开号：EP2345733A1

  公开（公告）日：2011-07-20

  In the present invention, an N-protected amino acid is obtained by producing an amino acid using a biocatalyst such as a microorganism and enzyme; acidizing the reaction mixture containing the amino acid to adjust pH to not more than 4, without isolating the amino acid; and then protecting the amino group under a basic condition. As a result, a high-quality N-protected amino acid can be quantitatively and efficiently produced using a quantitative or slightly excessive protecting agent, even when the amino acid produced using a biocatalyst is directly protected without isolating the amino acid.

  在本发明中，通过使用微生物和酶等生物催化剂生产氨基酸；将含有氨基酸的反应混合物酸化以调节 pH 值不超过 4，而不分离氨基酸；然后在碱性条件下保护氨基，即可获得 N-保护氨基酸。因此，即使使用生物催化剂生产的氨基酸是在不分离氨基酸的情况下直接保护的，使用定量或略微过量的保护剂也能定量、高效地生产出高质量的 N-保护氨基酸。
• Cosmetic composition
  申请人：UNILEVER PLC

  公开号：EP0572167B1

  公开（公告）日：1996-10-09
• CYANOPHOSPHONAMIDES AND METHOD FOR PREPARATION
  申请人：Monsanto Technology LLC

  公开号：EP1135398A1

  公开（公告）日：2001-09-26