3-苯基-2-[(2-苯基乙酰基)氨基]丙酸 | 54582-05-7

• 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: 3-苯基-2-[(2-苯基乙酰基)氨基]丙酸
• 英文名称: N-phenylacetyl-3-phenyl-alanine
• 英文别名: N²-benzoylphenylalanine；Phac-DL-Phe；N-PhAc-α-phenylalanine；N-phenylacetyl-phenylalanine；N-Phenylacetyl-phenylalanin；Phenacetyl-dl-phenylalanin；3-Phenyl-2-(2-phenylacetamido)propanoic acid；3-phenyl-2-[(2-phenylacetyl)amino]propanoic acid
• CAS: 54582-05-7
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: LIIPHJDKZNTNII-UHFFFAOYSA-N

物化性质

• 沸点：
  547.4±50.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-苯基-2-[(2-苯基乙酰基)氨基]丙酸 在 penicillin G acylase from Achromobacter sp. CCM 4824 、 水 作用下， 生成 L-苯丙氨酸
  参考文献：
  名称：

  Resolution of α/β-amino acids by enantioselective penicillin G acylase from Achromobacter sp .

  摘要：

  Penicillin G acylases (PGAs) are enantioselective enzymes catalyzing a hydrolysis of stable amide bond in a broad spectrum of substrates. Among them, derivatives of alpha- and beta-amino acids represent a class of compounds with high application potential. PGA(Ec) from Escherichia coil and PGA(A) from Achromobacter sp. CCM 4824 were used to catalyze enantioselective hydrolyses of seven selected N-phenylacetylated alpha/beta-amino acid racemates. The PGA(A) showed higher stereoselectivity for enantiomers of N-PhA-beta-homoleucine, N-PhAc-alpha-tert-leucine and N-PhAc-beta-leucine. To study the mechanism of enantiodiscrimination on molecular level, we have constructed a homology model of PGA(A) that was used in molecular docking experiments with the same substrates. In-silico experiments successfully reproduced the data from experimental enzymatic resolutions confirming validity of employed modeling protocol. We employed this protocol to evaluate enantiopreference of PGA(A) towards seven new substrates with application potential. For five of them, high enantioselectivity of PGA(A) was predicted. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.09.008
• 作为产物：
  描述：

  苯丙酮酸 在 盐酸 、 氨 作用下， 生成 3-苯基-2-[(2-苯基乙酰基)氨基]丙酸
  参考文献：
  名称：

  Ploechl, Chemische Berichte, 1883, vol. 16, p. 2815

  摘要：

  DOI：

文献信息

• Optimization of amino acid thioesters as inhibitors of metallo-β-lactamase L1
  作者：Xiao-Long Liu、Ke-Wu Yang、Yue-Juan Zhang、Ying Ge、Yang Xiang、Ya-Nan Chang、Peter Oelschlaeger

  DOI：10.1016/j.bmcl.2016.08.048

  日期：2016.10

  representing the amino acid side chain. Biological activity assays indicate that all of them are very potent inhibitors of L1 with an IC50 value range of 20-600nM, lower than those of most of the previously reported inhibitors of this scaffold. Analysis of structure-activity relationship reveals that big hydrophobic substituents on the N-terminus and a methionine amino acid side chain improves inhibitory activity

  金属β-内酰胺酶（MβLs）引起的抗生素耐药性的出现是一个全球性的公共卫生问题。最近，我们发现氨基酸硫酯是MβLL1抑制剂的高度有前途的支架。为了优化该系列抑制剂，通过修饰硫代酯N端的取代基和代表氨基酸侧链的基团，开发了九种新的氨基酸硫代酯。生物活性测定表明，它们都是非常有效的L1抑制剂，IC50值范围为20-600nM，低于大多数先前报道的该支架抑制剂的IC50值。结构-活性关系的分析表明，N-末端的大疏水取代基和蛋氨酸氨基酸侧链可改善硫酯的抑制活性。所有这些抑制剂都能够将β-内酰胺抗生素对产生L1的大肠杆菌BL21（DE3）细胞的抗菌活性恢复为对缺乏β-内酰胺酶的大肠杆菌的抗菌活性。对接研究表明，较大的N端疏水基团与在相同位置的较小疏水基团导致的结合方式略有不同。
• [EN] GRANZYME B DIRECTED IMAGING AND THERAPY<br/>[FR] IMAGERIE DU GRANZYME B ET THÉRAPIE DIRIGÉES CONTRE LE GRANZYME B
  申请人：CYTOSITE BIOPHARMA INC

  公开号：WO2019160916A1

  公开（公告）日：2019-08-22

  Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.

  本文提供了用于成像Granzyme B的杂环化合物。还提供了成像Granzyme B的方法、联合疗法以及包含Granzyme B成像试剂的试剂盒。
• Rhodium-catalysed racemisation of N-acyl α-amino acids
  作者：Martin J Hateley、Daniel A Schichl、Hans-Jörn Kreuzfeld、Matthias Beller

  DOI：10.1016/s0040-4039(00)00539-6

  日期：2000.5

  The first transition metal-catalysed racemisation of N-acyl α-amino acids, which is of importance for kinetic resolution processes, is described. Enantiomerically pure N-acyl α-amino acids were efficiently racemised under mild conditions using various rhodium complexes as catalysts, e.g. [Rh(cod)Cl]2, in the presence of phosphines.

  描述了N-酰基α-氨基酸的第一过渡金属催化的外消旋作用，这对于动力学拆分过程很重要。对映体纯的N-酰基α-氨基酸在温和条件下使用各种铑配合物作为催化剂可高效消旋。在膦存在下的[Rh（cod）Cl] 2。
• The use of cellulose (chromatography paper) as a cheap, versatile and non-covalent support for organic molecules during multi-step synthesis
  作者：Stephen E. Shanahan、Douglas D. Byrne、Graham G. A. Inglis、Mahbub Alam、Simon J. F. Macdonald

  DOI：10.1039/b208083d

  日期：2002.10.18

  Cellulose chromatography paper provides a novel non-covalent support for synthesis and in-situ purification of multi-dimensional arrays.

  纤维素色谱纸提供了一种新颖的非共价支持，用于多维阵列的合成和原位纯化。
• A New General Approach to Enantiomerically Pure Cyclic and Open-Chain (<i>R</i>)- and (<i>S</i>)-α,α-Disubstituted α-Amino Acids
  作者：Daniel Obrecht、Clive Spiegler、Peter Schönholzer、Klaus Müller、Heinz Heimgartner、Friedrich Stierli

  DOI：10.1002/hlca.19920750522

  日期：1992.8.13

  racemic N-acylated α,α-disubstituted amino acids were resolved by coupling to chiral amines 15-18 derived from (S)-phenylalanine to form diastereoisomers 19/20 or 21/22 that could be separated by crystallization and/or flash chromatography on silica gel (Scheme 3). Selective cleavage via the 1,3-oxazol-5(4H)-ones 10a-p gave the corresponding optically pure α,α-disubstituted amino-acid derivatives 11 or

  制备了各种各样的环状和开链α，α-二取代的α-氨基酸1a-p。通过与衍生自（S）-苯丙氨酸的手性胺15-18偶联，拆分外消旋N-酰化的α，α-二取代氨基酸，形成非对映异构体19/20或21/22，可以通过结晶和/或快速色谱分离在硅胶上（方案3）。通过1,3-恶唑-5（4 H）-酮10a-p的选择性裂解以高收率得到相应的光学纯α，α-二取代氨基酸衍生物11或12（方案3）。α，α-二取代氨基酸的绝对构型由非对映异构体20、21g'，22d的X射线结构确定。

表征谱图