(S)-2-氨基辛二酸 | 4254-88-0

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: (S)-2-氨基辛二酸
• 英文名称: L-2-aminosuberic acid
• 英文别名: L-amino suberic acid；(S)-2-Aminooctanedioic acid；(2S)-2-aminooctanedioic acid
• CAS: 4254-88-0
• 化学式: C₈H₁₅NO₄
• 分子量: 189.211
• InChiKey: YOFPFYYTUIARDI-LURJTMIESA-N

物化性质

• 沸点：
  385.5±37.0 °C(Predicted)
• 密度：
  1.229
• LogP：
  -0.075 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2922499990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  | 室温 |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: H-Asu-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: H-Asu-oh
CAS number: 4254-88-0

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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: C8H15NO4
Molecular weight: 189.2

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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

制备方法与用途

L-2-氨基琥珀酸是一种生物化学物质。

反应信息

• 作为反应物：
  描述：

  (S)-2-氨基辛二酸 在 盐酸 、 四甲基胍 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.67h， 生成 H-_L-ASu(OPMB)-OPMB*HCl
  参考文献：
  名称：

  A simple route to [11C]N-Me labeling of aminosuberic acid for proof of feasibility imaging of the xC− transporter

  摘要：

  Oxidative stress has been implicated in a variety of conditions, including cancer, heart failure, diabetes, neurodegeneration and other diseases. A potential biomarker for oxidative stress is the cystine/glutamate transporter, system x(C). L-Aminosuberic acid (L-ASu) has been identified as a system x(C) substrate. Here we report a facile method for [C-11]N-Me labeling of L-ASu, automation of the radiochemical process, and preliminary PET imaging with EL4 tumor bearing mice. The results demonstrate uptake in the tumor above background, warranting further studies on the use of radiolabeled analogs of L-ASu as a PET imaging agent for system x(C). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.004
• 作为产物：
  描述：

  6-氧代己酸甲酯 在 palladium on activated charcoal 盐酸 、 potassium tert-butylate 、 氢气 作用下， 以 二氯甲烷 、 二乙二醇二甲醚 、 丙酮 为溶剂， -78.0~25.0 ℃ 、405.3 kPa 条件下， 反应 74.0h， 生成 (S)-2-氨基辛二酸
  参考文献：
  名称：

  A Practical Enantioselective Synthesis of .alpha.-Amino Dicarboxylates. Preparation of D- and L-.alpha.-Aminoadipate, -.alpha.-Aminopimelate, and -.alpha.-Aminosuberate

  摘要：

  DOI：

  10.1021/jo00092a029

文献信息

• Interrogating Substrate Selectivity and Composition of Endogenous Histone Deacetylase Complexes with Chemical Probes
  作者：Alexander Dose、Julia Sindlinger、Jan Bierlmeier、Ahmet Bakirbas、Klaus Schulze-Osthoff、Stephanie Einsele-Scholz、Markus Hartl、Frank Essmann、Iris Finkemeier、Dirk Schwarzer

  DOI：10.1002/anie.201508174

  日期：2016.1.18

  three sets of probes, which derived from different acetylation sites, and sequence context was found to have a strong impact on substrate recognition and composition of HDAC complexes. By investigating K382 acetylation of the tumor suppressor p53 as an example, we further demonstrate that the interaction profiles reflect the catalytic activities of respective HDACs. These results underline the utility

  组蛋白脱乙酰基酶（HDAC）通过去除调节性赖氨酸残基上的乙酰化标记来调节众多细胞蛋白的功能和活性。我们开发了基于肽的HDAC探针，其中包含各种长度的异羟肟酸氨基酸，以在已知的乙酰化位点的背景下取代修饰的赖氨酸残基。使用来自不同乙酰化位点的三组探针研究了所有人类HDAC的相互作用谱，发现序列背景对底物识别和HDAC复合物的组成有很大影响。通过研究肿瘤抑制因子p53的K382乙酰化，我们进一步证明了相互作用谱反映了各个HDAC的催化活性。
• RAPAFUCIN DERIVATIVE COMPOUNDS AND METHODS OF USE THEREOF
  申请人：The Johns Hopkins University

  公开号：US20210094933A1

  公开（公告）日：2021-04-01

  The present disclosure provides macrocyclic compounds inspired by the immunophilin ligand family of natural products FK506 and rapamycin. The generation of a Rapafucin library of macrocyles that contain FK506 and rapamycin binding domains should have great potential as new leads for developing drugs to be used for treating diseases.

  本公开提供了受免疫蛋白配体家族FK506和雷帕霉素天然产物启发的大环化合物。生成包含FK506和雷帕霉素结合结构域的Rapafucin大环化合物库，应具有作为治疗疾病新药的潜力。
• Diheteropeptin, a Novel Substance with TGF-.BETA.-like Activity, Produced by a Fungus, Diheterospora chlamydosporia. II. Physico-chemical Properties and Structure Elucidation.
  作者：YUHTA MASUOKA、KAZUO SHIN-YA、KAZUO FIMIHATA、HISAO MATSUMO、YUKIHIRO TAKEBAYASHI、KOJI NAGAI、KJEN-ICHI SUZUKI、YOICHI HAYAKAWA、HARUO SETO

  DOI：10.7164/antibiotics.53.793

  日期：——

  The structure of diheteropeptin (1), a TGF-β-like active substance from Diheterospora chlamydosporia Q58044, was determined to be a new cyclotetrapeptide, cyclo[2-aminoisobutyryl-(S)-phenylalanyl-(R)-prolyl-(2S, 8R, 9R)-2-amino-8, 9-dihydroxydecanoyl-] by NMR, mass spectrometric and chemical studies.

  通过核磁共振、质谱和化学研究，确定了 Diheterospora chlamydosporia Q58044 中的一种 TGF-β-like 活性物质 diheteropeptin (1) 的结构，它是一种新的环四肽，即环[2-氨基异丁酰-(S)-苯丙氨酰-(R)-丙氨酰-(2S, 8R, 9R)-2-amino-8, 9-dihydroxydecanoyl-]。
• Structure Elucidation and Antimalarial Activity of Apicidin F: An Apicidin-like Compound Produced by <i>Fusarium fujikuroi</i>
  作者：Katharina Walburga von Bargen、Eva-Maria Niehaus、Klaus Bergander、Reto Brun、Bettina Tudzynski、Hans-Ulrich Humpf

  DOI：10.1021/np4006053

  日期：2013.11.22

  Apicidins are cyclic tetrapeptides with histone deacetylase inhibitory activity. Since their discovery in 1996 a multitude of studies concerning the activity against protozoa and certain cancer cell lines of natural and synthetic apicidin analogues have been published. Until now, the only published natural sources of apicidin are the fungus Fusarium pallidoroseum, later known as F. semitectum and two

  阿哌西丁是具有组蛋白脱乙酰基酶抑制活性的环状四肽。自从1996年发现以来，已经发表了许多有关天然和人工合成的阿比西丁类似物对原生动物和某些癌细胞系的活性的研究。到现在为止，apicidin的唯一公布的天然来源是真菌镰刀pallidoroseum，后来被称为F.半裸和两个未指明的镰刀菌菌株。芹菜素的生物合成起源可能与基因簇有关，并且已经提出了生物合成途径。最近，我们的研究小组首次能够鉴定出富士果黑穗病菌中的阿皮素样基因簇显然不会导致产生任何已知的阿皮苷类似物。通过过度表达途径特异性转录因子，我们能够鉴定出一种新的阿皮素样化合物。本研究提供了新化合物，称为阿匹西定F的完整结构解析。对恶性疟原虫的活性评估显示出良好的体外活性，IC 50值为0.67μM。
• Design, Synthesis, Potency, and Cytoselectivity of Anticancer Agents Derived by Parallel Synthesis from α-Aminosuberic Acid
  作者：Pia Kahnberg、Andrew J. Lucke、Matthew P. Glenn、Glen M. Boyle、Joel D. A. Tyndall、Peter G. Parsons、David P. Fairlie

  DOI：10.1021/jm050214x

  日期：2006.12.1

  differentiating agents to selectively kill cancer cells or transform them to a nonproliferating or normal phenotype could lead to cell- and tissue-specific drugs without the side effects of current cancer chemotherapeutics. This may be possible for a new generation of histone deacetylase inhibitors derived from amino acids. Structure-activity relationships are now reported for 43 compounds derived from 2-aminosuberic

  上个世纪的化学疗法的特征是不能区分癌细胞和正常细胞类型的细胞毒性药物，因此伴有通常限制剂量的毒性副作用。分化剂选择性杀死癌细胞或将其转化为非增殖或正常表型的能力可能导致细胞和组织特异性药物的产生，而没有当前癌症化学疗法的副作用。对于衍生自氨基酸的新一代组蛋白脱乙酰基酶抑制剂来说，这可能是可能的。现已报道了43种衍生自2-氨基磺酸的化合物的结构-活性关系，这些化合物可杀死多种癌细胞，其中26种是针对MM96L黑色素瘤细胞（IC50 20 nM-1 microM）的有效细胞毒素，而17种在杀死MM96L黑色素瘤细胞方面的选择性比正常（新生儿包皮成纤维细胞，NFF）细胞高5到60倍。与先前报道的衍生自半胱氨酸的化合物相比，这表示效力增加了10至100倍，并且选择性提高了多达10倍（J. Med。Chem。2004，47，2984）。选择性也被低估了，因为正常细胞NFF很少被所有药物杀死，这些药物