(2S)-2-氨基-6-氧代-6-苯基甲氧基己酸 | 38658-15-0

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2S)-2-氨基-6-氧代-6-苯基甲氧基己酸
• 英文名称: (S)-2-amino-6-(benzyloxy)-6-oxohexanoic acid
• 英文别名: (2S)-2-azaniumyl-6-oxo-6-phenylmethoxyhexanoate
• CAS: 38658-15-0
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: UQLRAAASUFVOLL-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (2S)-2-氨基-6-氧代-6-苯基甲氧基己酸 在 palladium on activated charcoal 、 氢气 、 N,N-二异丙基乙胺 、 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， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.25h， 生成 (((S)-1-carboxy-5-((3-fluorobenzyl)(methyl)amino)-5-oxopentyl)carbamoyl)-L-glutamic acid
  参考文献：
  名称：

  2-Aminoadipic Acid–C(O)–Glutamate Based Prostate-Specific Membrane Antigen Ligands for Potential Use as Theranostics

  摘要：

  The design and synthesis of prostate specific membrane antigen (PSMA) ligands derived from 2-aminoadipic acid, a building block that has not previously been used to construct PSMA. ligands, are reported. The effects of both the linker length and of an N-substituent of our PSMA ligands were probed, and X-ray structures of five of these ligands bound to PSMA were obtained. Among the ligands disclosed herein, 13b showed the highest inhibitory activity for PSMA. As ligand 13b can readily be radiolabeled since its fluorine atom is adjacent to the nitrogen atom of its pyridine ring, the use of this and related compounds as theranostics can be pursued.

  DOI：

  10.1021/acsmedchemlett.8b00318
• 作为产物：
  描述：

  2-Acetylamino-hexanedioic acid dibenzyl ester 在 cobalt(II) chloride 作用下， 以 水 为溶剂， 生成 (2S)-2-氨基-6-氧代-6-苯基甲氧基己酸
  参考文献：
  名称：

  串联酶解产生L-α-氨基链烷二酸ω-酯。

  摘要：

  丝氨酸蛋白酶（α-胰凝乳蛋白酶或枯草杆菌蛋白酶BPN'）和曲霉属氨酰酶对外消旋N-乙酰基-α-氨基链烷二酸α，ω-二酯的串联作用，收率高，光学旋光性好。纯度。通过肟树脂的固相合成和环化裂解方法，将由此获得的L-α-氨基异丁二酸ω-酯方便地引入催产素类似物[Asu1,6]催产素中。

  DOI：

  10.1248/cpb.44.212

文献信息

• [EN] CASPASE INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE CASPASE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：CONATUS PHARMACEUTICALS INC

  公开号：WO2020181165A1

  公开（公告）日：2020-09-10

  Provided herein are compounds of formula (I), compositions comprising the compounds and method of treating various diseases with the compounds and compositions.

  本文提供了公式（I）的化合物，包括这些化合物的组合物以及使用这些化合物和组合物治疗各种疾病的方法。
• Synthesis of peptide analogs of prothrombin precursor sequence 5-9. Substrate specificity of vitamin K dependent carboxylase
  作者：Daniel H. Rich、S. Russ Lehrman、Megumi Kawai、Hedda L. Goodman、John W. Suttie

  DOI：10.1021/jm00138a013

  日期：1981.6

  Thirty-five analogues of Phe-Leu-Glu-Glu-Leu, the pentapeptide sequence 5-9 of bovine prothrombin precursor, were synthesized and assayed as potential substrates or inhibitors of rat liver vitamin K dependent carboxylase. Carboxylation of substrate was determined by measuring the incorporation of carbon-24 labeled bicarbonate into product. Changes in substrate carboxylation produced by changing peptide

  合成了Phe-Leu-Glu-Glu-Leu的三十五个类似物，即牛凝血酶原前体的五肽序列5-9，并作为大鼠肝脏维生素K依赖性羧化酶的潜在底物或抑制剂进行了测定。通过测量碳-24标记的碳酸氢盐在产品中的掺入量来确定底物的羧基化程度。测量了通过改变肽链长度，氨基酸手性或将肽链主链与羧基分开的距离而产生的底物羧化的变化。数据表明，羧化酶使L-谷氨酸残基羧化，而没有使L-天冬氨酸，L-高谷氨酸，谷氨酰胺或D-谷氨酸残基羧化。三通五肽是比单或双（氨基酸）衍生物更好的底物，加到N端的疏水基团可以为酶产生更好的底物。没有一种合成底物能像酶的内源蛋白质底物一样有效地被羧化。讨论了结构对影响羧基化的其他参数的影响。
• Decarboxylative Side-Chain Functionalization of Aspartic/Glutamic Acids Using Two-Molecule Photoredox Catalysts
  作者：Yudai Shinkawa、Toshiki Furutani、Takumi Ikeda、Mugen Yamawaki、Toshio Morita、Yasuharu Yoshimi

  DOI：10.1021/acs.joc.2c01606

  日期：2022.9.2

  functionalization of aspartic/glutamic acid derivatives through photoinduced decarboxylation was achieved by using organic two-molecule photoredox catalysts without racemization under mild conditions. A facile process involving the preparation of substrates and photoinduced decarboxylative radical additions can provide easy access to the linked amino acids with carbohydrates and amino acids at the side chain

  天冬氨酸/谷氨酸衍生物通过光诱导脱羧的侧链功能化是通过在温和条件下使用有机双分子光氧化还原催化剂实现的，无需外消旋化。涉及制备底物和光诱导脱羧自由基加成的简便方法可以提供容易获得与侧链处的碳水化合物和氨基酸连接的氨基酸。
• Synthesis and biological evaluation of boron peptide analogues of Belactosin C as proteasome inhibitors
  作者：Hiroyuki Nakamura、Mizuyoshi Watanabe、Hyun Seung Ban、Wataru Nabeyama、Akira Asai

  DOI：10.1016/j.bmcl.2009.04.103

  日期：2009.6

  A series of boron peptides 11, 13, 15 and 17 were designed and synthesized as proteasome inhibitors based on the structure of Belactosin C. Matteson homologation was a key step in the synthesis of the boron peptides. Compounds 11a and 13 showed significant inhibition of 20S proteasome chymotrypsin-like (beta 5) activity (IC(50) = 0.28 and 0.51 mu M, respectively). Furthermore, like PS-341, compound 11a increased the G2/M cell distribution. A biparametric cytofluorimetric analysis with FITC-labeled annexin V and propidium iodide showed induction of apoptosis by compound 11a at >1 mu M concentrations of compound. (C) 2009 Elsevier Ltd. All rights reserved.
• Potent and Fully Noncompetitive Peptidomimetic Inhibitor of Multidrug Resistance P-Glycoprotein
  作者：Ophélie Arnaud、Ali Koubeissi、Laurent Ettouati、Raphaël Terreux、Ghina Alamé、Catherine Grenot、Charles Dumontet、Attilio Di Pietro、Joëlle Paris、Pierre Falson

  DOI：10.1021/jm100839w

  日期：2010.9.23

  N-alpha-Boc-L-Asp(OBn)-L-Lys(Z)-OtBu (reversin 121, I), an inhibitor of the P-gp ABC transporter, was used to conceive compounds inhibiting the drug efflux occurring through the Hoechst 33342 and daunorubicin transport sites of P-gp, respectively H and R sites. Replacement of the aspartyl residue by trans-4-hydroxy-L-proline (4(R)Hyp) gave compounds 11 and 15 characterized by half-maximal inhibitory concentrations (1050) of 0.6 and 0.2 mu M, which are 2- and 7-fold lower than that of the parent molecule. The difference in IC50 between 11 and 15 rests on the carbonyl group of the peptidyl bond, reduced in 15. Those compounds are rather specific of P-gp, having no or limited activity on MRP1 and BCRP. 15 displayed no marked cytotoxicity up to 10-fold its IC50. Importantly, 15 equally inhibited the Hoechst 33342 and daunorubicin effluxes through a typical noncompetitive inhibition mechanism, suggesting its binding to a site different from the and R drug-transport sites.