乙酰基-L-苏氨酸 | 17093-74-2

• 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 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 乙酰基-L-苏氨酸
• 中文别名: N-乙酰基-L-苏氨酸
• 英文名称: N-acetyl-DL-theanine
• 英文别名: N-acetyl-DL-Thr；N-acetyl-threonine；(+/-)-threo-2-Acetamino-3-hydroxy-buttersaeure；N-Acetyl-threonin；N-Acetyl-DL-threonin；N-Acetylthreonine；(2S,3R)-2-acetamido-3-hydroxybutanoic acid
• CAS: 17093-74-2
• 化学式: C₆H₁₁NO₄
• 分子量: 161.158
• InChiKey: PEDXUVCGOLSNLQ-WUJLRWPWSA-N

物化性质

• 熔点：
  125-128°C
• 沸点：
  443.3±40.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于甲醇（轻微）、水（轻微、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36
• 海关编码：
  2924199090
• 储存条件：
  存储于室温下。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ac-thr-oh
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Ac-thr-oh
CAS number: 17093-74-2

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C6H11NO4
Molecular weight: 161.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  乙酰基-L-苏氨酸 在 盐酸 作用下， 以 水 为溶剂， 反应 2.5h， 以566 mg的产率得到D-别苏氨酸
  参考文献：
  名称：

  Improved synthesis of d-allothreonine derivatives from l-threonine

  摘要：

  The improved synthesis of protected D-allothreonine derivatives [Fmoc-D-alloThr(Bu-t)-OH (1) and Fmoc-D-alloThr-(OBu)-Bu-t (2)] is described. The epimerization of cheap L-threonine (L-Thr) (3) with catalytic salicylaldehyde afforded a mixture of L-Thr (3) and D-alloThr (4) and separation of ammonium salt gave D-alloThr (4) in 96% de. The chemoselective deprotection of tert-butyl ether or tert-butyl ester of Fmoc-D-alloThr(Bu-t)-(OBu)-Bu-t (5) easily succeeded in converting Fmoc-D-alloThr(Bu-t)-OH (1) or Fmoc-D-alloThr-(OBu)-Bu-t (2), respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.027
• 作为产物：
  描述：

  L-苏氨酸 在 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 反应 2.5h， 生成 乙酰基-L-苏氨酸
  参考文献：
  名称：

  Improved synthesis of d-allothreonine derivatives from l-threonine

  摘要：

  The improved synthesis of protected D-allothreonine derivatives [Fmoc-D-alloThr(Bu-t)-OH (1) and Fmoc-D-alloThr-(OBu)-Bu-t (2)] is described. The epimerization of cheap L-threonine (L-Thr) (3) with catalytic salicylaldehyde afforded a mixture of L-Thr (3) and D-alloThr (4) and separation of ammonium salt gave D-alloThr (4) in 96% de. The chemoselective deprotection of tert-butyl ether or tert-butyl ester of Fmoc-D-alloThr(Bu-t)-(OBu)-Bu-t (5) easily succeeded in converting Fmoc-D-alloThr(Bu-t)-OH (1) or Fmoc-D-alloThr-(OBu)-Bu-t (2), respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.027

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。
• [EN] NOVEL GLUTAMINE ANTAGONISTS AND USES THEREOF<br/>[FR] NOUVEAUX ANTAGONISTES DE LA GLUTAMINE ET LEURS UTILISATIONS
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2019071110A1

  公开（公告）日：2019-04-11

  Glutamine antagonists and their use for treating oncological, immunological, and neurological diseases are disclosed. Also disclosed are methods for treating an oncological, immunological, infectious or neurological disease or disorder, the method comprising administering to a subject in need of treatment thereof a therapeutically effective amount of a glutamine antagonist of the disclosure or the pharmaceutical composition thereof. Also disclosed are methods of enhancing the effects of an immune checkpoint inhibitor, enabling a subject to respond to an immune checkpoint inhibitor, or enabling the toxicity or the dose or number of treatments with an immune checkpoint inhibitor to be reduced, comprising administering to a subject in need of treatment thereof a therapeutically effective amount of a glutamine antagonist of the disclosure or the pharmaceutical composition thereof, and an immune checkpoint inhibitor. Also disclosed are methods for treating an oncological, immunological, infectious or neurological disease or disorder that is refractory to checkpoint inhibitor therapy, the method comprising administering to a subject in need thereof, and having the refractory disease or disorder, a therapeutically effective amount of a glutamine antagonist of the disclosure or the pharmaceutical composition thereof.

  谷氨酰胺拮抗剂及其用于治疗肿瘤、免疫和神经系统疾病的方法已被披露。还披露了治疗肿瘤、免疫、传染性或神经系统疾病或紊乱的方法，该方法包括向需要治疗的受试者施用本公开的谷氨酰胺拮抗剂或其药物组成的治疗有效量。还披露了增强免疫检查点抑制剂效果的方法，使受试者对免疫检查点抑制剂产生反应，或减少免疫检查点抑制剂的毒性或剂量或治疗次数的方法，包括向需要治疗的受试者施用本公开的谷氨酰胺拮抗剂或其药物组成的治疗有效量，以及免疫检查点抑制剂。还披露了治疗对检查点抑制剂疗法无效的肿瘤、免疫、传染性或神经系统疾病或紊乱的方法，该方法包括向需要治疗的受试者施用本公开的谷氨酰胺拮抗剂或其药物组成的治疗有效量。
• [EN] MEBENDAZOLE PRODRUGS WITH ENHANCED SOLUBILITY AND ORAL BIOAVAILABILITY<br/>[FR] PROMÉDICAMENTS DE MÉBENDAZOLE À SOLUBILITÉ ET BIODISPONIBILITÉ ORALE AMÉLIORÉES
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2019157338A1

  公开（公告）日：2019-08-15

  Prodrugs of mebendazole and methods for their use in treating a disease, disorder, or disorder, including cancer, are disclosed.

  甲苯咪唑的前药及其在治疗疾病、紊乱或障碍，包括癌症中的使用方法被披露。
• Direct monitoring of biocatalytic deacetylation of amino acid substrates by ¹H NMR reveals fine details of substrate specificity
  作者：Silvia De Cesare、Catherine A. McKenna、Nicholas Mulholland、Lorna Murray、Juraj Bella、Dominic J. Campopiano

  DOI：10.1039/d1ob00122a

  日期：——

  Amino acids are key synthetic building blocks that can be prepared in an enantiopure form by biocatalytic methods. We show that the L-selective ornithine deacetylase ArgE catalyses hydrolysis of a wide-range of N-acyl-amino acid substrates. This activity was revealed by 1H NMR spectroscopy that monitored the appearance of the well resolved signal of the acetate product. Furthermore, the assay was used

  氨基酸是关键的合成构件，可以通过生物催化方法制备对映体纯形式。我们发现L-选择性鸟氨酸脱乙酰酶 ArgE 催化多种N-酰基氨基酸底物的水解。该活性通过1 H NMR 光谱来揭示，该光谱监测了乙酸盐产物的清晰信号的出现。此外，该测定还使用可以采用不同旋转异构体构象的底物来探测生物催化剂的微妙结构选择性。
• Cosmetic composition
  申请人：UNILEVER PLC

  公开号：EP0415598A1

  公开（公告）日：1991-03-06

  A composition suitable for topical application to mammalian skin and hair for inducing, maintaining or increasing hair growth comprises a hair growth promoter chosen from N-acylated amino-acids, in which the acyl group has from 2 to 20 carbon atoms, together with a cosmetically acceptable vehicle for the hair growth promoter.

  适用于哺乳动物皮肤和头发的局部应用的组合物，用于诱导、维持或增加头发生长，包括选择自N-酰化氨基酸的头发生长促进剂，其中酰基含有2至20个碳原子，以及用于头发生长促进剂的化妆品可接受载体。