(2R,3S)-3-氨基-2-羟基-4-苯丁酸 | 62023-63-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物
• 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: (2R,3S)-3-氨基-2-羟基-4-苯丁酸
• 英文名称: (2R,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid
• 英文别名: (2R,3S)-3-azaniumyl-2-hydroxy-4-phenylbutanoate
• CAS: 62023-63-6
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: LDSJMFGYNFIFRK-DTWKUNHWSA-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

安全信息

• 海关编码：
  2922509090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332
• 储存条件：
  存储条件：2-8°C，密封保存，置于干燥处，避光，并在惰性气体环境中。

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-氨基-2-羟基-4-苯丁酸 在 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 methyl ((2R,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4-phenylbutano-yl)leucinate
  参考文献：
  名称：

  用于治疗癌症的新型 HDAC/CD13 双抑制剂的设计、合成和生物学评价

  摘要：

  氨肽酶N（APN/CD13）在肿瘤进展中发挥作用，但其抑制剂缺乏细胞毒性，在癌症治疗中用作辅助药物。组蛋白脱乙酰酶 (HDAC) 是一种表观遗传靶标，HDAC 抑制剂具有细胞毒性，并与其他抗癌药物表现出协同作用。本研究合理设计合成了一系列新型HDAC/CD13双重抑制剂，将CD13抑制剂的抗转移、抗侵袭作用与HDAC抑制剂的细胞毒作用结合起来。代表性化合物12对人CD13、HDAC1-3表现出比阳性对照贝他汀和SAHA更有效的抑制活性和抗增殖活性。化合物12有效诱导MV4-11细胞凋亡，同时将A549细胞阻滞在G2/M期。此外，12比单一抑制剂32和38表现出明显更好的抗转移和抗侵袭作用，表明它是一种有前景的抗癌药物，有待进一步研究。

  DOI：

  10.1016/j.ejmech.2023.115752
• 作为产物：
  描述：

  (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid 在 钯 氢气 作用下， 生成 (2R,3S)-3-氨基-2-羟基-4-苯丁酸
  参考文献：
  名称：

  Synthesis and structure-activity relations of bestatin analogs, inhibitors of aminopeptidase B

  摘要：

  Stereoisomers and analogues of bestatin, [(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]-L-leucine, were synthesized and tested for aminopeptidase B and leucine aminopeptidase inhibiting activity. Among the eight stereoisomers, the 2S stereoisomers exhibited strong activity. In a series of compounds in which the L-leucine residue of bestatin was substituted with other amino acids, only the one containing isoleucine showed more activity than bestatin. Norleucine, norvaline, methionine, valine, serine, glutamine, phenylalanine, glutamic acid, proline, and lysine analogues gave, in that order, decreasing activity. Alkyl and phenyl sub stitution for the benzyl group of bestatin decreased the activity markedly. p-Methyl-, p-chloro-, and p-nitrobestatins showed greater activity than bestatin.

  DOI：

  10.1021/jm00214a010

文献信息

• Production method of beta-amino-alpha-hydroxycarboxylic acid
  申请人：AJINOMOTO CO. INC

  公开号：US20020151722A1

  公开（公告）日：2002-10-17

  The present invention provides a production method of an optically active &bgr;-amino-&agr;-hydroxycarboxylic acid, which includes the following steps (a)-(c): (a) treating an optically active N-carbamate protected &bgr;-amino epoxide with an acid to give an optically active 5-hydroxymethyl-2-oxazolidinone; (b) oxidizing the resulting compound in the presence of 2,2,6,6-tetramethyl-1-piperidinyloxy and hypochlorite to give an optically active 4-benzyl-2-oxo-5-oxazolidinecarboxylic acid; and (c) treating the 4-benzyl-2-oxo-5-oxazolidinecarboxylic acid with a base, and a production method of an optically active N-carbamate protected &bgr;-amino-&agr;-hydroxycarboxylic acid which includes protection of the amino group with a carbamate type protecting group. The industrial production method of the present invention can produce these compounds efficiently.

  本发明提供了一种光学活性β-氨基-α-羟基羧酸的生产方法，包括以下步骤(a)-(c)：(a) 用酸处理光学活性N-羰基保护的β-氨基环氧化合物，得到光学活性5-羟甲基-2-噁唑烷酮；(b) 在2,2,6,6-四甲基-1-哌啶氧和次氯酸盐存在下氧化所得化合物，得到光学活性4-苄基-2-氧代-5-噁唑烷羧酸；(c) 用碱处理4-苄基-2-氧代-5-噁唑烷羧酸，并且提供了一种光学活性N-羰基保护的β-氨基-α-羟基羧酸的生产方法，其中包括用羰酸酯型保护基保护氨基团。本发明的工业生产方法可以高效地生产这些化合物。
• Highly Stereoselective Intramolecular S_N2′ Cyclization Yielding Chiral ­Oxazolidin-2-ones: General Route to α-Hydroxy-β-amino Acids
  作者：Ki Hun Park、Woo Duck Seo、Marcus J. Curtis-Long、Jin Hyo Kim、Jong Keun Park、Ki Min Park

  DOI：10.1055/s-2005-872264

  日期：——

  Intramolecular nucleophilic attack onto allylsulfonates promoted by silica gel acting as an acid catalyst provides expedient stereoselective access to 4,5-difunctionalized oxazolidin-2-ones. Precursors were prepared efficiently from enantiopure α-amino acids and subsequent manipulation of the oxazolidin-2-ones yielded enantiopure α-hydroxy-β-amino acids.

  硅胶作为酸催化剂促进对烯丙基磺酸盐的分子内亲核攻击提供了对 4,5-双官能化 2-酮的立体选择性访问。前体是由对映纯的 α-氨基酸有效制备的，随后对恶唑烷-2-酮的操作产生了对映纯的 α-羟基-β-氨基酸。
• Process for producing norstatin derivatives
  申请人：Kaneka Corporation

  公开号：US06281379B1

  公开（公告）日：2001-08-28

  This invention to provide a process for producing an optically active threo-phenylnorstatin derivative which does not require a toxic cyanating agent or a costly reagent, or a complicated procedure, and can be practiced on a commercial scale. This invention is directed to a process for producing a &bgr;-amino-&agr;-hydroxy acid derivative which comprises treating either a &ggr;-amino-&bgr;-keto sulfoxide derivative with a halogenating agent to produce a &ggr;-amino-&agr;-halo-&bgr;-keto sulfoxide derivative, treating the same with an acid and an alcohol to produce a &bgr;-amino-&agr;-keto ester derivative or &bgr;-amino-&agr;-keto acid derivative, and followed by reducing.

  这项发明提供了一种生产光学活性的threo-phenylnorstatin衍生物的方法，该方法不需要有毒的氰化剂或昂贵的试剂，也不需要复杂的程序，可以在商业规模上实施。这项发明涉及一种生产β-氨基-α-羟基酸衍生物的方法，包括用卤化剂处理γ-氨基-β-酮亚砜衍生物以产生γ-氨基-α-卤-β-酮亚砜衍生物，再用酸和醇处理相同物质以产生β-氨基-α-酮酯衍生物或β-氨基-α-酮酸衍生物，最后进行还原。
• PROCESSES FOR PRODUCING OXAZOLIDINONE DERIVATIVE OF BETA-HYDROXYETHYLAMINE COMPOUND AND FOR PRODUCING BETA-HYDROXYETHYLAMINE COMPOUND
  申请人：KANEKA CORPORATION

  公开号：EP1403257A1

  公开（公告）日：2004-03-31

  The present invention provides a process of starting from N-alkoxycarbonyl-ethylamine compounds having a leaving group at the β-position to prepare oxazolidinone derivatives of β-hydroxyethylamine compounds having an inverted steric configuration at the β-position carbon, which comprises introducing a step of treating in contact with water with heating under acidic to neutral conditions into the process. Also, the present invention provides a process of starting from N-alkoxycarbonyl-ethylamine compounds having a leaving group at the β-position to prepare β-hydroxyethylamine compounds having an inverted steric configuration at the β-position carbon, which comprises subjecting the oxazolidinone derivatives prepared as described above to a step of treating in contact with water under basic conditions.

  本发明提供了一种从在β-位置具有离去基团的N-烷氧羰基乙基胺化合物出发，制备具有β-位置碳上反转立体构型的β-羟基乙基胺化合物的噁唑烷酮衍生物的方法，该方法包括在过程中引入与水接触并在酸性至中性条件下加热处理的步骤。此外，本发明提供了一种从在β-位置具有离去基团的N-烷氧羰基乙基胺化合物出发，制备具有β-位置碳上反转立体构型的β-羟基乙基胺化合物的方法，该方法包括将上述制备的噁唑烷酮衍生物在与水接触的步骤中在碱性条件下处理。
• Heteroaryl-ethanolamine derivatives as antiviral agents
  申请人：——

  公开号：US20040110787A1

  公开（公告）日：2004-06-10

  The present invention provides a compound of formula as described herein, which are useful as antiviral agents, in particular, as agents against viruses of the herpes family.

  本发明提供了一种如下式的化合物，其作为抗病毒剂具有用途，特别是作为对抗疱疹家族病毒的剂：