threo-3-Benzyl-serin

• 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: threo-3-Benzyl-serin
• 英文别名: 4-Phenyl-threonine；(2S,3R)-2-amino-3-hydroxy-4-phenylbutanoic acid
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: CMGJFSCKGIKDJV-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  threo-3-Benzyl-serin 在 磷化氢 、 氢碘酸 作用下， 生成 DL-高苯丙氨酸
  参考文献：
  名称：

  Neue aliphatische 2-Amino-3-hydroxysäuren, II

  摘要：

  DOI：

  10.1515/bchm2.1964.337.1.40
• 作为产物：
  描述：

  氧化苯乙烯 在 L-threonine transaldolase ObiH 作用下， 以 aq. buffer 为溶剂， 生成 threo-3-Benzyl-serin
  参考文献：
  名称：

  α-芳基醛作为 C-C 键形成生物催化级联中的中间体的高效化学酶合成

  摘要：

  多酶生物催化级联正在成为合成复杂生物活性分子的实用途径。然而，水稳性碳亲电子试剂的相对稀少限制了由这种级联制成的分子的合成复杂性。在这里，我们开发了一个化学酶平台，该平台利用氧化苯乙烯异构酶 (SOI) 通过 Meinwald 重排将易于获得的芳基环氧化物转化为 α-芳基醛。然后，这些不稳定的醛中间体被 C-C 键形成酶 ObiH 拦截，ObiH 催化转醛酶与l-苏氨酸的反应，产生具有合成挑战性的 β-羟基-α-氨基酸。两种酶在大肠杆菌中的共表达产生能够合成各种立体纯非标准氨基酸 (nsAA) 的全细胞生物催化剂，并且可以以克规模生产。我们使用同位素标记的底物来探索 SOI 的机制，我们证明它可以催化具有立体特异性 1,2-氢化物转移的协同异构化。通过用最近设计的脱羧醛缩酶拦截它们以产生 γ-羟基 nsAA，进一步确定了原位生成的 α-芳基醛的可行性。总之，这些数据建立了一种在简单的全细胞条件下生产

  DOI：

  10.1021/acscatal.2c02369

文献信息

• NOVEL IMIDAZOLIDINONE DERIVATIVE, METHOD OF PRODUCING THE SAME AND METHOD OF PRODUCING OPTICALLY ACTIVE AMINO ACID
  申请人：Saka Yasuhiro

  公开号：US20090209768A1

  公开（公告）日：2009-08-20

  The objective of the present invention is to provide an optically active imidazolidinone derivative widely usable for synthesizing an optically active amino acid, a method of easily producing the derivative, and a method of easily producing an optically active amino acid by using the derivative. The objective can be achieved by producing an optically active amino acid using a novel optically active imidazolidinone derivative represented by a general formula (3) and the like. According to the method of the present invention, an optically active imidazolidinone derivative can be obtained by preferential crystallization from a mixture of isomers of the imidazolidinone derivative. Therefore, an optically active amino acid can be easily and stereoselectively produced without cumbersome procedures required for the conventional methods, such as resolution of diastereomers, synthesis from an optically active amino acid and resolution of isomers by silica gel column chromatography.

  本发明的目的是提供一种光学活性咪唑啉酮衍生物，可广泛用于合成光学活性氨基酸，以及一种易于生产该衍生物的方法和利用该衍生物轻松生产光学活性氨基酸的方法。该目的可通过使用一般公式（3）等表示的新型光学活性咪唑啉酮衍生物来生产光学活性氨基酸来实现。根据本发明的方法，可以通过优先结晶从咪唑啉酮衍生物的异构体混合物中获得光学活性咪唑啉酮衍生物。因此，可以轻松地、立体选择性地生产光学活性氨基酸，而无需传统方法所需的繁琐程序，例如对映体的分离、从光学活性氨基酸合成和通过硅胶柱层析分离异构体的合成。
• Synthesis, Stability, and Antimicrobial Activity of (+)-Obafluorin and Related .beta.-Lactone Antibiotics
  作者：Yunlong Pu、Christopher Lowe、Miloslav Sailer、John C. Vederas

  DOI：10.1021/jo00092a025

  日期：1994.7

  Optically pure obafluorin(l), an antibacterial agent from Pseudomonas fluorescens, was synthesized in six steps via lactonization of N-[(2-nitrophenyl)sulfenyl]-(2S,3R)-2-amino-3-hydroxy-4-(4-nitrophenyl)butanoic acid (12a), which was prepared in a stereospecific manner from 4-nitrophenylacetaldehyde (9a) and (S)-1-benzoyl-2-tert-butyl-3-methyl-4-imidazolidinone (7). A series of analogues was then synthesized in order to probe structural features required for antibacterial activity as well as those responsible for the hydrolytic decomposition of 1 to the corresponding hydroxy acid 23a. Analogues 22b and 22e wherein the nitro group of 1 is replaced with hydrogen and chlorine, respectively, were prepared in a fashion similar to 1, as were the N-acetyl, N-benzoyl, and N-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl (ATMO) derivatives 24a-c. The tosylate salt of L-threonine-beta-lactone (21) was transformed to a series of N-acylated derivatives including the following: 22d (2,3-dihydroxybenzoyl), 25 (2-hydroxybenzoyl), 27 (3,4-dihydroxybenzoyl), 29 (4'methyl-2,2'-bipyridine-4-carbonyl), 31 (epsilon-(L-alpha-aminoadipoyl)), 34 ((N'-2,3-dihydroxybenzoyl)-beta-alanyl), 35 (bromoacetyl), 36 ((6-purinylthio)acetyl), and 37 ((4-pyridylthio)acetyl). The results show that a-amino beta-lactones bearing an N-acyl group with an o- or p-hydroxybenzoyl moiety are especially prone to decomposition under aqueous conditions and that this effect is enhanced by replacement of the 4-nitrobenzyl group on the oxetanone ring of 1 with a methyl. The N-(3,4-dihydroxybenzoyl)L-threonine beta-lactone (27) converts slowly in the solid state to (4S,5S)-2-(3,4-dihydroxybenzoyl)-5-methyl-2-oxazoline-4-carboxylic acid (39b), which hydrolyzes rapidly in 4:1 CD3CN:D2O to O-(3,4-dihydroxybenzoyl)-L-allothreonine (38b). Direct hydrolysis of 27 to 38b under the same conditions has a half-life of 2.4 days. Preliminary assays for antibacterial activity indicate that 29 has nearly comparable activity to obafluorin(l) but is much more stable. The (2-nitrophenyl)sulfenyl p-lactones 14 and 41, as well as the N-(phenylsulfenyl)-L-threonine beta-lactone (44), are the most active agents in the biological assays.
• US4370318A
  申请人：——

  公开号：US4370318A

  公开（公告）日：1983-01-25
• US4473554A
  申请人：——

  公开号：US4473554A

  公开（公告）日：1984-09-25
• US7947722B2
  申请人：——

  公开号：US7947722B2

  公开（公告）日：2011-05-24