N-benzoyl-DL-threonine | 7469-23-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苏氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzoyl-DL-threonine
• 英文别名: N-Benzoyl-DL-threonin；N-Benzoyl-DL-threonin；Benzoyl-DL-threonin；N-Benzoyl-L-threonine；(2S,3R)-2-benzamido-3-hydroxybutanoic acid
• CAS: 7469-23-0
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: IOQIWWTVXOPYQR-APPZFPTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 安全说明：
  S22,S24/25

反应信息

• 作为反应物：
  描述：

  N-benzoyl-DL-threonine 在 氢溴酸 作用下， 生成 L-苏氨酸
  参考文献：
  名称：

  West; Carter, Journal of Biological Chemistry, 1937, vol. 119, p. 104,105

  摘要：

  DOI：
• 作为产物：
  描述：

  O-benzoyl-DL-threonine 在 sodium hydroxide 作用下， 生成 N-benzoyl-DL-threonine
  参考文献：
  名称：

  126.苏氨酸的恶唑啉衍生物的立体化学。苏氨酸合成的改进

  摘要：

  DOI：

  10.1039/jr9490000589

文献信息

• Reactivity of α-Amino Acids in the Reaction with Esters in Aqueous–1,4-Dioxane Media
  作者：L. B. Kochetova、T. P. Kustova、L. V. Kuritsyn

  DOI：10.1134/s1070363218010127

  日期：2018.1

  The kinetics of the reaction of a series of α-amino acids with 4-nitrophenyl acetate, 4-nitrophenyl benzoate, and 2,4,6-trinitrophenyl benzoate in aqueous 1,4-dioxane medium has been studied. Kinetics of the reactions involving 4-nitrophenyl acetate and 2,4,6-trinitrophenyl benzoate has complied with the Brønsted dependence and revealed linear correlation between rate constant logarithm and the energy

  研究了一系列α-氨基酸与4-硝基苯基乙酸酯，4-硝基苯基苯甲酸酯和2,4,6-三硝基苯基苯甲酸酯在1,4-二恶烷水溶液中的反应动力学。涉及乙酸4-硝基苯酯和2,4,6-三硝基苯甲酸苯酯的反应动力学符合布朗斯台德依赖性，并揭示了速率常数对数与α-氨基酸阴离子前沿轨道的能量差之间的线性关系。
• Discovery and Lead Optimization of a Novel Series of CC Chemokine Receptor 1 (CCR1)-Selective Piperidine Antagonists via Parallel Synthesis
  作者：Cullen L. Cavallaro、Stephanie Briceno、Jing Chen、Mary Ellen Cvijic、Paul Davies、John Hynes、Rui-Qin Liu、Sandhya Mandlekar、Anne V. Rose、Andrew J. Tebben、Katy Van Kirk、Andrew Watson、Hong Wu、Guchen Yang、Percy H. Carter

  DOI：10.1021/jm300896d

  日期：2012.11.26

  A series of novel, potent CCR1 inhibitors was developed from a moderately active hit using an iterative parallel synthesis approach. The initial hit (composed of three subunits: an amine, a central amino acid, and an N-terminal cap) became the basis for a series of parallel chemical libraries designed to generate SAR data. Libraries were synthesized that explored each of the three subunits; the CCR1

  使用迭代平行合成方法，从中等活性的化合物中开发出了一系列新型有效的CCR1抑制剂。最初的命中物（由三个亚基组成：胺，中心氨基酸和N端帽）成为一系列旨在生成SAR数据的平行化学文库的基础。合成了探索三个亚基中每个亚基的文库。获得的CCR1结合数据显示以下：（1）对胺的变化没有很好的耐受性；（2）在分子中心优选小的烷基氨基酸；（3）在N端的取代通常被很好地容忍。这些数据被用来推动系列的优化，最终为引线提供了28 nM的CCR1结合IC 50（48）。该铅对小鼠显示出对CCR1的选择性高于其他CCR家族成员，具有很高的微粒体稳定性和良好的药代动力学。
• Studies on Acylase Activity and Microorganisms. XIX Optical Resolution of Threonine, Lysine, Tryptophan, and Methionine by Acylase of Soil Bacteria
  作者：Yukio Kameda、Katsuhiko Matsui、Yukio Kimura、Etsuko Toyoura、Masako Kimura

  DOI：10.1248/cpb.10.1146

  日期：——

  Fifteen strains (KT 202, KT 205, KT 207, etc.) of soil bacteria capable of asymmetric hydrolysis of N-benzoyl-DL-threonine, 2, 6-di-N-benzoyl-DL-lysine, N-acetyl-DLlysine, N-acetyl-DL-tryptophan or N-acetyl-DL-methionine were isolated by using a synthetic medium containing N-acyl-derivatives of amino acids as the sole source of carbon (Table I). N-Benzoyl-DL-threonine was asymmetrically hydrolyzed to L-threonine, N-benzoyl-D-threonine and benzoic acid by the acylase of KT 218, KT 229, and KT 83, while 2, 6-di-N-benzoyl-DL-lysine, to 6-N-benzoyl-L-lysine, 2, 6-di-N-benzoyl-D-lysine and benzoic acid by KT 218 and KT 229. KT 241 and KT 224 hydrolyzed asymmetrically N- acetyl- DL-tryptophan and N-acetyl-DL-methionine to L-tryptophan and N-acetyl-D-tryptophan, and L-methionine and N-acetyl-D-methionine, respectively. It was observed that N-acetyl-D-tryptophan and N-acetyl-D-methionine were hydrolyzed by several strains (KT 229, KT 83, KT 222, etc.) of soil bacteria. It seems of interest to note that N-acetyl-L-methionine was more easily hydrolyzed by KT 224 or KT 218 than N-acetyl-L-tryptophan, while the latter was more easily hydrolyzed by KT 241, and that the N-acetyl derivative of L-methionine was more easily hydrolyzed by KT 224 or KT 241 than the N-benzoyl derivative, while the latter was more easily hydrolyzed by KT 218.

  通过使用含有氨基酸N-酰基衍生物作为唯一碳源的合成培养基，分离出15株能够不对称水解N-苯甲酰-DL-苏氨酸、2,6-二N-苯甲酰-DL-赖氨酸、N-乙酰-DL-赖氨酸、N-乙酰-DL-色氨酸或N-乙酰-DL-蛋氨酸的土壤细菌（见表I）。N-苯甲酰-DL-苏氨酸在KT 218、KT 229和KT 83的酰化酶作用下不对称水解为L-苏氨酸、N-苯甲酰-D-苏氨酸和苯甲酸，而2,6-二N-苯甲酰-DL-赖氨酸则在KT 218和KT 229的作用下水解为6-N-苯甲酰-L-赖氨酸、2,6-二N-苯甲酰-D-赖氨酸和苯甲酸。KT 241和KT 224则分别将N-乙酰-DL-色氨酸和N-乙酰-DL-蛋氨酸不对称水解为L-色氨酸和N-乙酰-D-色氨酸以及L-蛋氨酸和N-乙酰-D-蛋氨酸。观察到N-乙酰-D-色氨酸和N-乙酰-D-蛋氨酸被若干株土壤细菌（如KT 229、KT 83、KT 222等）水解。值得注意的是，N-乙酰-L-蛋氨酸比N-乙酰-L-色氨酸更容易被KT 224或KT 218水解，而后者则更容易被KT 241水解。此外，L-蛋氨酸的N-乙酰衍生物比N-苯甲酰衍生物更容易被KT 224或KT 241水解，而后者则更容易被KT 218水解。
• In tube determination of the absolute configuration of α- and β-hydroxy acids by NMR via chiral BINOL borates
  作者：Félix Freire、Emilio Quiñoá、Ricardo Riguera

  DOI：10.1039/b806529b

  日期：——

  A simple NMR methodology, through the formation of chiral BINOL borates in the NMR tube, and that reunites the advantages of chiral derivatizing (CDAs) and chiral solvating agents (CSAs), is presented for the assignment of the absolute configuration of alpha- and beta-hydroxy acids.

  提出了一种简单的NMR方法，该方法通过在NMR管中形成手性BINOL硼酸酯，并重新组合了手性衍生化（CDA）和手性溶剂化剂（CSA）的优点，用于分配α-和β的绝对构型-羟基酸。
• [EN] PROCESS FOR PREPARATION OF (DL) -NOREPINEPHRINE ACID ADDITION SALT, A KEY INTERMEDIATE OF (R) - (-) - NOREPINEPHRINE<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN SEL D'ADDITION D'ACIDE DE NORÉPINÉPHRINE (DL), INTERMÉDIAIRE CLÉ DE LA NORÉPINÉPHRINE (R) - (-) -
  申请人：NEON LAB LTD

  公开号：WO2013008247A1

  公开（公告）日：2013-01-17

  The invention discloses a process for preparation of (dl)-norepinephrine salt by reacting 3,4-dihydroxy-a-haloacetophenone with hexamethylenetetramine to provide hexamine salt; followed by hydrolysis and hydrogenation. The invention also discloses a novel intermediate formed in the process and its synthesis.

  该发明揭示了一种制备(dl)-去甲肾上腺素盐的方法，通过将3,4-二羟基-α-卤代乙酰苯酮与六亚甲基四胺反应以提供六胺盐；随后进行水解和氢化。该发明还揭示了该过程中形成的一种新型中间体及其合成方法。

表征谱图