D-炔丙基甘氨酸 | 23235-03-2

• 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: D-炔丙基甘氨酸
• 英文名称: (R)-2-aminopent-4-ynoic acid
• 英文别名: D-propargylglycine；(2R)-2-aminopent-4-ynoic acid
• CAS: 23235-03-2
• 化学式: C₅H₇NO₂
• mdl: MFCD00237407
• 分子量: 113.116
• InChiKey: DGYHPLMPMRKMPD-SCSAIBSYSA-N

物化性质

• 熔点：
  205℃
• 沸点：
  272.1±35.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  <p><b></b></p>

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  2

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：
  H315,H319,H335
• 储存条件：
  <p><br></p>

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: D-Propargylglycine
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: D-Propargylglycine
CAS number: 23235-03-2

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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: C5H7NO2
Molecular weight: 113.1

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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

合成制备方法

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用途

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反应信息

• 作为反应物：
  描述：

  D-炔丙基甘氨酸 在 盐酸 、 硫酸 、 sodium nitrite 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 生成 (R)-2-hydroxypent-4-ynoic acid methyl ester
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 8. Pharmacological Optimization of Orally Bioavailable 2-Pyridone-Containing Peptidomimetics

  摘要：

  The optimization of the pharmacokinetic performance of various 2-pyridone-containing human rhinovirus (HRV) 3C protease (3CP) inhibitors following oral administration to either beagle dogs or CM-monkeys is described. The molecules described in this work are composed of a 2-pyridone-containing peptidomimetic binding determinant and an alpha,beta-unsaturated ester Michael acceptor moiety which forms an irreversible covalent adduct with the active site cysteine residue of the 3C enzyme. Modification of the ester contained within these compounds is detailed along with alteration of the P-2 substituent present in the peptidomimetic portion of the inhibitors. The pharmacokinetics of several inhibitors in both dogs and monkeys are described (7 h plasma concentrations after oral administration) along with their human plasma stabilities, stabilities in incubations with human, dog, and monkey microsomes and hepatocytes, Caco-2 permeabilities, and aqueous solubilities. Compounds containing an alpha,beta-unsaturated ethyl ester fragment and either an ethyl or propargyl. P-2 moiety displayed the most promising combination of 3C enzyme inhibition (k(obs)/[1] 170 000-223 000 M-1 s(-1)), antiviral activity (EC50 = 0.047-0.058 muM, mean vs seven HRV serotypes), and pharmacokinetics following oral administration (7 h dog plasma levels = 0.248-0.682 muM; 7 h CM-monkey plasma levels = 0.057-0.896 muM).

  DOI：

  10.1021/jm030166l
• 作为产物：
  描述：

  (R)-methyl 2-aminopent-4-ynoate 在 盐酸 、 methyloxirane 作用下， 以84%的产率得到D-炔丙基甘氨酸
  参考文献：
  名称：

  Schoellkopf; Hartwig; Pospischil, Synthesis, 1981, vol. No. 12, # 12, p. 966 - 969

  摘要：

  DOI：

文献信息

• Chloroalanyl and propargylglycyl dipeptides. Suicide-substrate-containing antibacterials
  作者：Kam Sing Cheung、Steven A. Wasserman、Edward Dudek、Stephen A. Lerner、Michael Johnston

  DOI：10.1021/jm00366a015

  日期：1983.12

  A set of dipeptides containing the amino acid residues beta-chloroalanine and propargylglycine, which are mechanism-based inactivators of purified microbial enzymes (alanine racemase and cystathionine gamma-synthase, respectively), have been synthesized, and their antibacterial properties in vitro have been evaluated. Dipeptides containing a single beta-chloro-L-alanyl residue (e.g., 3, 5, 9, and 10)

  合成了一组包含氨基酸残基β-氯丙氨酸和炔丙基甘氨酸的二肽，它们是纯化的微生物酶（分别为丙氨酸消旋酶和胱硫醚γ-合酶）的基于机理的失活剂，并已评估了它们的体外抗菌性能。含有单个β-氯-L-丙氨酰基残基（例如3、5、9和10）或单个L-炔丙基糖基残基（例如12和15）的二肽是有效的抗菌剂。通过将这些残基掺入二肽中，β-氯-L-丙氨酸和L-炔丙基甘氨酸的体外抗生素活性可增加多达4000倍。仅包含单个酶灭活氨基酸以及第二个L-丙氨酰基残基（3、5、12和15）的化合物的活性范围有限：仅无乳链球菌，金黄色葡萄球菌和表皮葡萄球菌敏感。然而，含有两个自杀底物残基的肽[例如，β-Cl-LAla-β-Cl-LAla（8）或LppGly-LppGly（18）]是广谱抗菌剂；在被调查的16种物种中，多达12种是敏感物种。含有氨基末端的L-甲硫酰基（9）或L-净戊酰基（10）残基和羧基末端的β-氯-L-丙氨酰基单
• D-ALA-D-ALA-BASED DIPEPTIDES AS TOOLS FOR IMAGING PEPTIDOGLYCAN BIOSYNTHESIS
  申请人：INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION

  公开号：US20160222430A1

  公开（公告）日：2016-08-04

  Disclosed herein are compositions for assessing peptidoglycan biosynthesis in bacteria using modified dipeptides containing a bioorthogonal tag and applying novel post-labeling methods to label the bioorthogonal tag. The resultant, labeled peptidoglycan structures are amenable for identifying bacteria by microscopic visualization.

  本文披露了一种用含有生物正交标记的修饰二肽评估细菌中肽聚糖生物合成的组合物，并应用新颖的后标记方法来标记生物正交标记。标记后的肽聚糖结构适合通过显微镜观察来识别细菌。
• Towards the development of activity-based probes for detection of lysine-specific demethylase-1 activity
  作者：Maria E. Ourailidou、Alessia Lenoci、Clemens Zwergel、Dante Rotili、Antonello Mai、Frank J. Dekker

  DOI：10.1016/j.bmc.2016.11.043

  日期：2017.2

  scientists to develop diagnostic tools in order to explore the function of this enzyme. In this work, we present our efforts on the development of tranylcypromine (TCP)-based functionalized probes for activity-based protein profiling (ABPP) of LSD1 activity. Biotinylated forms of selected compounds enabled dose-dependent enzyme labeling of recombinant LSD1. However, treatment with LSD1 inhibitors did not

  赖氨酸特异性去甲基化酶 1 (LSD1) 在肿瘤发生中的意义促使科学家们开发诊断工具以探索这种酶的功能。在这项工作中，我们展示了我们在开发基于反苯环丙胺 (TCP) 的功能化探针以用于 LSD1 活性的基于活性的蛋白质分析 (ABPP) 方面的努力。所选化合物的生物素化形式能够对重组 LSD1 进行剂量依赖性酶标记。然而，用 LSD1 抑制剂处理并没有明显降低 LSD1 标记效率，因此表明使用这些探针进行标记不依赖于活性。这需要替代策略来开发 LSD1 酶的 ABPP 探针。
• [EN] 5-[5-[2-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-2-METHYLPROPANOYLMETHYLAMINO]-4-(4-FLUORO-2-METHYLPHENYL)]-2-PYRIDINYL-2-ALKYL-PROLINAMIDE AS NK1 RECEPTOR ANTAGONISTS<br/>[FR] 5- [5- [2- (3, 5-BIS (TRIFLUOROMÉTHYL) PHÉNYL) -2-MÉTHYLPROPANOYLMÉTHYLAMINO] -4- (4-FLUORO-2-MÉTHYLPHÉNYL) ] -2-PYRIDINYL-2-ALKYL-PROLINAMIDE, ANTAGONISTES DU RÉCEPTEUR NK1
  申请人：GLAXO WELLCOME MFG PTE LTD

  公开号：WO2009138393A1

  公开（公告）日：2009-11-19

  The invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein R is C1-4 alkyl useful in the treatment of diseases and conditions for which antagonism of NK1 receptor is beneficial.

  该发明提供了一种式（I）的化合物或其药用可接受的盐，其中R为C1-4烷基，在治疗需要NK1受体拮抗作用有益的疾病和症状中有用。
• Novel Compounds
  申请人：Alvaro Giuseppe

  公开号：US20090286836A1

  公开（公告）日：2009-11-19

  The invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein R is C 1-4 alkyl useful in the treatment of diseases and conditions for which antagonism of NK1 receptor is beneficial.

  该发明提供了式(I)的化合物或其药用可接受的盐，其中R为C1-4烷基，在治疗需要NK1受体拮抗作用有益的疾病和症状中有用。