D-丙氨酰胺 | 35320-22-0

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 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-丙氨酰胺
• 英文名称: D-alaninamide
• 英文别名: D-alanine amide；(R)-2-aminopropanamide；2-aminopropanenitrile；(R)-alaninamide；(R)-H-Ala-NH2；R-AlaNH2；(2R)-2-aminopropanamide
• CAS: 35320-22-0
• 化学式: C₃H₈N₂O
• mdl: MFCD00672501
• 分子量: 88.1093
• InChiKey: HQMLIDZJXVVKCW-UWTATZPHSA-N

物化性质

• 熔点：
  74-76 °C
• 沸点：
  247.4±23.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  69.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2924199090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: D-Alaninamide
Synonyms: (2R)-2-Aminopropanamide

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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-Alaninamide
CAS number: 35320-22-0

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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: C3H8N2O
Molecular weight: 88.1

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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

反应信息

• 作为反应物：
  描述：

  D-丙氨酰胺 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 三氟甲磺酸酐 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 (2R)-2-azidopropanamide
  参考文献：
  名称：

  [EN] HETEROARYL NITRILE COMPOUNDS USEFUL AS INHIBITORS OF CATHEPSIN-S
  [FR] COMPOSÉS D'HÉTÉROARYL-NITRILE UTILES COMME INHIBITEURS DE CATHEPSINE-S

  摘要：

  揭示了具有以下化学式（I）的Cathepsin-S可逆抑制剂化合物，可用于治疗自身免疫和其他疾病。还揭示了含有这些化合物的药物组合物，以及制备和使用这些化合物的方法。

  公开号：

  WO2011109470A1
• 作为产物：
  描述：

  D-丙氨酸 在 氨 作用下， 以 乙醇 为溶剂， 生成 D-丙氨酰胺
  参考文献：
  名称：

  Inhibitors of farnesyl-protein transferase

  摘要：

  本发明涉及抑制法尼基-蛋白转移酶（FTase）和致癌基因蛋白Ras法尼酰化的化合物。该发明还涉及含有本发明化合物的化疗组合物以及抑制法尼基-蛋白转移酶和致癌基因蛋白Ras法尼酰化的方法。

  公开号：

  US05939439A1

文献信息

• Thioester analogues of peptidoglycan fragment MurNAc-L-Ala-γ-D-Glu as substrates for peptidoglycan hydrolase MurNAc-L-Ala amidase
  作者：Ross L. Harding、Joanne Henshaw、Joannah Tilling、Timothy D. H. Bugg

  DOI：10.1039/b200921h

  日期：2002.7.11

  MurNAc-L-amidase is one of a family of peptidoglycan hydrolases which catalyses the breakdown of bacterial peptidoglycan. Analogues of the peptidoglycan fragment MurNAc-L-Ala-γ-D-Glu containing S-thiolactic acid in place of L-alanine were synthesised as thioester substrates for this enzyme. Triphenylmethanethiol was used to develop a stereoselective synthesis of S-thiolactic acid, which was elaborated synthetically into MurNAc-dipeptide analogues. MurNAc-S-thioacetyl-N-propylamide 13 and MurNAc-S-thiolactyl-2R-alaninamide 16 were found not to be substrates for recombinant MurNAc-L-Ala amidases CwlA from Bacillus subtilis and Ply21 from bacteriophage TP21, however, turnover of tripeptide thioester S-propionylthiolactyl-γ-D-Glu-L-Lys-OMe 21 was observed using amidase Ply21. Therefore, recognition of the amino acid at position 3 of the pentapeptide sidechain appears to be important for enzymatic turnover.

  MurNAc-L-酰胺酶是催化细菌肽聚糖分解的肽聚糖水解酶家族之一。合成了一种硫酯底物，即将肽聚糖片段MurNAc-L-Ala-γ-D-Glu中的L-丙氨酸替换为S-硫乳酸的类似物。利用三苯基甲硫醇开发了S-硫乳酸的手性选择性合成方法，并进一步合成了MurNAc二肽类似物。发现MurNAc-S-硫乙酰基-N-丙基酰胺13和MurNAc-S-硫乳酰基-2R-丙氨酰胺16不是枯草芽孢杆菌重组MurNAc-L-Ala酰胺酶CwlA和噬菌体TP21的Ply21的底物，但观察到三肽硫酯S-丙酰基硫乳酰基-γ-D-Glu-L-赖氨酸甲酯21在Ply21酰胺酶的作用下发生了转氨反应。因此，对于酶促转氨反应来说，识别五肽侧链上第3位的氨基酸似乎很重要。
• Peptide Synthesis with α-(Difluoromethyl)-Substituted α-Amino Acids
  作者：Thomas Michel、Beate Koksch、Sergei N. Osipov、Alexander S. Golubev、Joachim Sieler、Klaus Burger

  DOI：10.1135/cccc20021533

  日期：——

  Methodology for the incorporation of α-(difluoromethyl)-substituted α-amino acids into N- and C-terminal positions of dipeptides as well as into position 2 of tri- and tetrapeptides is described.

  将α-(二氟甲基)-取代的α-氨基酸并入二肽的N-和C-末端位置，以及并入三肽和四肽的位置2的方法被描述。
• Diastereoselectivity in prebiotically relevant 5(4H)-oxazolone-mediated peptide couplings
  作者：Damien Beaufils、Grégoire Danger、Laurent Boiteau、Jean-Christophe Rossi、Robert Pascal

  DOI：10.1039/c3cc49580a

  日期：——

  out as the first part of a systems chemistry investigation of potential paths for symmetry breaking. Substantial diastereomeric excesses result from a fast epimerization of the 5(4H)-oxazolone intermediate in aqueous solution.

  进行了可能的益生元肽形成反应的立体化学研究，作为系统化学研究对称断裂潜在途径的第一部分。非对映异构体的大量过量是由于5（4H）-恶唑酮中间体在水溶液中的快速差向异构化。
• KDS2010, a Newly Developed Reversible MAO-B Inhibitor, as an Effective Therapeutic Candidate for Parkinson’s Disease
  作者：Min-Ho Nam、Jong-Hyun Park、Hyo Jung Song、Ji Won Choi、Siwon Kim、Bo Ko Jang、Hyung Ho Yoon、Jun Young Heo、Hyowon Lee、Heeyoung An、Hyeon Jeong Kim、Sun Jun Park、Doo-Wan Cho、Young-Su Yang、Su-Cheol Han、Sangwook Kim、Soo-Jin Oh、Sang Ryong Jeon、Ki Duk Park、C. Justin Lee

  DOI：10.1007/s13311-021-01097-4

  日期：2021.7

  Monoamine oxidase-B (MAO-B) is a well-established therapeutic target for Parkinson’s disease (PD); however, previous clinical studies on currently available irreversible MAO-B inhibitors have yielded disappointing neuroprotective effects. Here, we tested the therapeutic potential of KDS2010, a recently synthesized potent, selective, and reversible MAO-B inhibitor in multiple animal models of PD. We designed and synthesized a series of α-aminoamide derivatives and found that derivative KDS2010 exhibited the highest potency, specificity, reversibility, and bioavailability (> 100%). In addition, KDS2010 demonstrated significant neuroprotective and anti-neuroinflammatory efficacy against nigrostriatal pathway destruction in the mouse MPTP model of parkinsonism. Treatment with KDS2010 also alleviated parkinsonian motor dysfunction in 6-hydroxydopamine-induced and A53T mutant α-synuclein overexpression rat models of PD. Moreover, KDS2010 showed virtually no toxicity or side effects in non-human primates. KDS2010 could be a next-generation therapeutic candidate for PD.

  单胺氧化酶-B（MAO-B）是帕金森病（PD）的一个被广泛认可的治疗靶点；然而，先前对目前可用的不可逆MAO-B抑制剂进行的临床研究显示出令人失望的神经保护效果。在这里，我们测试了KDS2010的治疗潜力，这是一种最近合成的强效、选择性和可逆的MAO-B抑制剂，在多个PD动物模型中进行了测试。我们设计并合成了一系列α-氨酰胺衍生物，并发现衍生物KDS2010表现出最高的效力、特异性、可逆性和生物利用度（> 100%）。此外，KDS2010在小鼠MPTP帕金森病模型中表现出显著的神经保护和抗神经炎症效果，对黑质纹状体通路的破坏具有显著作用。KDS2010治疗还缓解了6-羟基多巴胺诱导和A53T突变α-突触核蛋白过表达大鼠PD模型的帕金森病运动功能障碍。此外，KDS2010在非人灵长类动物中几乎没有毒性或副作用。KDS2010可能是PD的下一代治疗候选药物。
• B(OCH₂CF₃)₃-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether
  作者：Valerija Karaluka、Rachel M. Lanigan、Paul M. Murray、Matthew Badland、Tom D. Sheppard

  DOI：10.1039/c5ob01801c

  日期：——

  The direct amidation of pharmaceutically relevant carboxylic acids and amines with B(OCH₂CF₃)₃ in cyclopentyl methyl ether (CPME) is described.

  在环戊基甲醚（CPME）中，使用B(OCH2CF3)3直接对具有药用相关性的羧酸和胺进行酰胺化反应。