乙酰基甘氨酸 N-羟基丁二酰亚胺酯 | 24715-24-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 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: 乙酰基甘氨酸 N-羟基丁二酰亚胺酯
• 中文别名: 乙酰基甘氨酸N-羟基丁二酰亚胺酯
• 英文名称: N-acetylglycine N-hydroxysuccinimide ester
• 英文别名: N-acetylglycine succinimidyl ester；2,5-dioxopyrrolidin-1-yl N-acetylglycinate；SuO-Gly-NAc；N-acetylglycine-OSu；Ac-Gly-Osu；(2,5-dioxopyrrolidin-1-yl) 2-acetamidoacetate
• CAS: 24715-24-0
• 化学式: C₈H₁₀N₂O₅
• 分子量: 214.178
• InChiKey: YLVAAZXLYPUDRS-UHFFFAOYSA-N

物化性质

• 密度：
  1.41±0.1 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2925190090
• 储存条件：
  -20°C，干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ac-gly-osu
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-gly-osu
CAS number: 24715-24-0

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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: C8H10N2O5
Molecular weight: 214.2

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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：

  乙酰基甘氨酸 N-羟基丁二酰亚胺酯 、 5-氨基乙酰丙酸盐酸盐 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  有效合成5-氨基戊酸（ALA）的肽，用于光动力疗法

  摘要：

  已经设计了一种有效且具有成本效益的方法来制备氨基甲酸酯保护的5-氨基戊二酸（5-ALA）二肽酯衍生物，该方法避免了在碱性条件下与5-ALA的不稳定性相关的问题。该方法还适用于以高对映体纯度直接合成N-（α）-乙酰基氨基酸-ALA二肽，作为光动力疗法（PDT）的潜在新药。

  DOI：

  10.1016/j.tet.2005.05.036
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 N-乙酰甘氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 乙酰基甘氨酸 N-羟基丁二酰亚胺酯
  参考文献：
  名称：

  5-亚芳基-3-取代的四酸作为催化不对称加氢的可能底物的合成和光谱研究

  摘要：

  一系列新的5-芳基-3-取代特特拉姆酸6-19通过3-丁酰基特特拉姆酸的缩合反应合成了3，3-乙氧羰基特特拉姆酸4和3 -乙酰基特特拉姆酸5与各种取代的苯甲醛的。使用FT-IR，1 H和13 C-NMR光谱，FAB-MS光谱以及元素分析已阐明了分离的化合物6-19的结构。

  DOI：

  10.1002/jhet.5570380527

文献信息

• [EN] STABILITY-MODULATING LINKERS FOR USE WITH ANTIBODY DRUG CONJUGATES<br/>[FR] LIEURS MODULANT LA STABILITÉ DESTINÉS À ÊTRE UTILISÉS AVEC DES CONJUGUÉS ANTICORPS-MÉDICAMENT
  申请人：PFIZER

  公开号：WO2016030791A1

  公开（公告）日：2016-03-03

  The present invention provides stability-modulated antibody-drug conjugates, stability-modulating linker components used to make these stability-modulated antibody-drug conjugates, therapeutic methods using stability-modulated antibody-drug conjugates, and methods of making stability modulating linkers and stability-modulated antibody-drug conjugates.

  本发明提供了稳定性调节的抗体药物偶联物，用于制造这些稳定性调节的抗体药物偶联物的稳定性调节连接器组分，使用稳定性调节的抗体药物偶联物的治疗方法，以及制造稳定性调节连接器和稳定性调节的抗体药物偶联物的方法。
• POLYSUBUNIT OPIOID PRODRUGS RESISTANT TO OVERDOSE AND ABUSE
  申请人：Elysium Therapeutics, Inc.

  公开号：US20170100390A1

  公开（公告）日：2017-04-13

  The invention provides compositions and methods for the treatment or prevention of pain. The invention provides constructs whereby hydrolysis of the construct by a specified gastrointestinal enzyme directly, or indirectly, releases an opioid when taken orally as prescribed. The gastrointestinal enzyme mediated release of opioid from constructs of the invention is designed to be attenuated in vivo via a saturation or inhibition mechanism when overdoses are ingested. The invention further provides constructs that are highly resistant to oral overdose, chemical tampering, and abuse via non-oral routes of administration.

  这项发明提供了用于治疗或预防疼痛的组合物和方法。该发明提供了构造物，通过指定的胃肠酶在口服时直接或间接地水解构造物释放阿片类物质。该发明中构造物中的胃肠酶介导的阿片类物质释放被设计为在体内通过饱和或抑制机制在摄入过量时减弱。该发明进一步提供了对口服过量、化学篡改和通过非口服途径滥用高度抵抗的构造物。
• Diversity-oriented chemical modification of heparin: Identification of charge-reduced N-acyl heparin derivatives having increased selectivity for heparin-binding proteins
  作者：Liusheng Huang、Robert J. Kerns

  DOI：10.1016/j.bmc.2005.11.013

  日期：2006.4

  modification of heparin is shown to afford charge-reduced heparin derivatives that possess increased selectivity for binding heparin-binding proteins. Variable N-desulfonation of heparin was employed to afford heparin fractions possessing varied levels of free amine. These N-desulfonated heparin fractions were selectively N-acylated with structurally diverse carboxylic acids using a parallel synthesis

  肝素以多样性为导向的化学修饰显示可提供电荷减少的肝素衍生物，该衍生物具有增强的结合肝素结合蛋白的选择性。肝素的可变N-脱磺作用被用于提供具有不同水平的游离胺的肝素级分。使用并行合成规程，使用结构多样的羧酸将这些N-脱硫的肝素级分选择性地N-酰化，以生成133种肝素衍生结构的文库。筛选文库成员以比较对肝素结合蛋白的亲和力，发现独特的肝素衍生结构对单个肝素结合蛋白具有更高的亲和力和选择性。而且，以前证明肝素结合特定蛋白质所需的肝素中的N-磺基已被结构上多样化的非阴离子部分所取代，以鉴定与未修饰肝素相比具有等同或增加亲和力的结合这些蛋白质的电荷降低的肝素衍生物。本文所述方法概述了我们认为适用于天然聚阴离子多糖的系统化学修饰和合成寡糖制备的过程，以鉴定与肝素结合蛋白的电荷降低的高亲和力配体。
• Design and synthesis of a peptide derivative of ametantrone targeting the major groove of the d(GGCGCC)₂palindromic sequence
  作者：Alberto Ongaro、Giovanni Ribaudo、Emmanuelle Braud、Mélanie Ethève-Quelquejeu、Michele De Franco、Christiane Garbay、Luc Demange、Nohad Gresh、Giuseppe Zagotto

  DOI：10.1039/c9nj03817e

  日期：——

  residue in order to selectively target palindromic sequences of DNA of malignant cells. The peptide arms are linked to the ametantrone core through 1,2,3-triazole. According to our docking prediction, this compound should be double-stranded β-sheet structured, and it has been designed to interact with two guanine residues upstream from a central d(CpG)2 intercalation site on each DNA strand, owing to the

  在肿瘤学中，一些DNA嵌入剂已在化学疗法中用于根除癌细胞多年，但是这些药物通常缺乏对恶性组织的选择性，因此会引起主要的副作用。我们在此报告了抗肿瘤嵌入剂金刚烷胺的设计和合成，该药物与包括中央Lys残基的两个相同的肽臂互补，以选择性靶向恶性细胞DNA的回文序列。肽臂通过1,2,3-三唑连接到金刚酮核心。根据我们的对接预测，该化合物应为双链β-折叠结构，并且已设计为与中心d（CpG）2上游的两个鸟嘌呤残基相互作用。由于涉及肽臂的Lys末端侧链铵基团的H键，每个DNA链上都有一个插入位点。由于聚合途径的合成，获得了这种新的金刚烷酮衍生物，其关键步骤是在金刚烷酮核心上进行双亲核取代，然后进行“双位” 1,3-偶极环加成，几乎得到1,4-二取代的三唑接头数量上。通过质谱进行的初步结合测定证明了其对DNA回文序列的准确性。评价了该化合物对三种癌细胞系和一种健康细胞系的细胞毒性，并将其与米托蒽醌（米曲酮
• An efficient synthesis of novel N-acetyl-3-alkanoyl and 3-dienoyl tetramic acids
  作者：Margarita Petroliagi、Olga Igglessi-Markopoulou

  DOI：10.1039/a702649h

  日期：——

  A general synthesis of N-acetyl-3-alkanoyl- and 3-dienoyl-tetramic acids is presented. The condensation of N-(N-acetylglycyloxy)succinimide with β-keto esters bearing alkanoyl or dienoyl groups furnishes the new 3-substituted N-acetyltetramic acids 6–9 and 16 in good yields. The key intermediates 4 and 5 have been isolated and subsequently cyclized to the corresponding tetramic acids. Spectral data

  提出了N-乙酰基-3-链烷酰基-和3-二壬基-四甲酸的一般合成方法。N-（N-乙酰基乙氧基氧基）琥珀酰亚胺与带有烷酰基或二烯酰基的β-酮酯的缩合可提供高收率的新型3取代的N-乙酰基四酸6–9和16。已分离出关键中间体4和5，随后环化为相应的四酸。报告了所有化合物的光谱数据和物理特性。