3-氯-L-丙氨酸 | 2731-73-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丙氨酸类衍生物
• 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: 3-氯-L-丙氨酸
• 中文别名: L-3-氯丙氨酸；(S)-3-氯丙氨酸；S-3-氯-丙氨酸
• 英文名称: 2-amino-3-chloropropanoic acid
• 英文别名: β-chloro-L-alanine；(R)-2-amino-3-chloropropanoic acid；3-chloro-L-alanine；β-Chloralanin；(2R)-2-azaniumyl-3-chloropropanoate
• CAS: 2731-73-9
• 化学式: C₃H₆ClNO₂
• mdl: MFCD00066125
• 分子量: 123.539
• InChiKey: ASBJGPTTYPEMLP-REOHCLBHSA-N

物化性质

• 熔点：
  156 °C
• 沸点：
  243.6±30.0 °C(Predicted)
• 密度：
  1.2776 (rough estimate)
• 溶解度：
  DMSO（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25
• 危险品标志：
  C
• 海关编码：
  2922499990
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  密封储存，应存放在阴凉、干燥的库房中。

SDS

Name:	3-Chloro-L-alanine Material Safety Data Sheet
Synonym:
CAS:	2731-73-9

Section 1 - Chemical Product MSDS Name:3-Chloro-L-alanine Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2731-73-9	3-Chloro-L-alanine		unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 2731-73-9: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C3H6ClNO2
Molecular Weight: 123.5005

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Not available.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2731-73-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Chloro-L-alanine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 2731-73-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2731-73-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2731-73-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

β-氯- L-丙氨酸是一种抑制多种酶的抑菌氨基酸类似物，能够抑制包括苏氨酸脱氨酶和支链氨基酸转氨酶（Branched-Chain Amino Acid Transaminase, BCAA-T）、L-天冬氨酸脱羧酶以及 α-氨基酮戊酸合成酶（可能还包括 O-乙酰丝氨酸硫氢基酶）。

靶点

细菌

体外研究

β-氯- L-丙氨酸可以抑制苏氨酸脱氨酶、支链氨基酸转氨酶 (Branched-Chain Amino Acid Transaminase, BCAA-T)、L-天冬氨酸脱羧酶以及 α-氨基酮戊酸合成酶。此外，它还能可逆性地抑制大肠杆菌 K-12 的丙氨酸-缬氨酸转氨酶（Transaminase C）。这种抑制作用加上对支链氨基酸转氨酶的抑制作用解释了在 β-氯- L-丙氨酸存在时大肠杆菌需要异亮氨酸和缬氨酸的需求。在β-氯- L-丙氨酸的存在下，沙门氏菌志贺株 LT2 的生长需求可能是由于其对支链氨基酸转氨酶的抑制所致。

反应信息

• 作为反应物：
  描述：

  3-氯-L-丙氨酸 反应 0.33h， 生成 piruvate
  参考文献：
  名称：

  Suzuki, Seibun; Hirahara, Toshikatsu; Shim, Jae-Kuk, Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 1, p. 84 - 89

  摘要：

  DOI：
• 作为产物：
  描述：

  L-丝氨酸 在 盐酸 、 氯化亚砜 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 20.17h， 以32.6 g的产率得到3-氯-L-丙氨酸
  参考文献：
  名称：

  Processes for producing &bgr;-halogeno-&agr;-amino-carboxylic acids and phenylcysteine derivatives and intermediates thereof

  摘要：

  提供一种在工业上有利的生产β-卤代-α-氨基羧酸的方法。还提供了生产具有高光学纯度的N-保护-S-苯基半胱氨酸及其中间体的方法，其中利用了上述生产方法。公开了一种生产β-卤代-α-氨基羧酸或其盐的方法，包括使用酸和卤化试剂卤化β-羟基-α-氨基羧酸（其中α-位置的氨基基团的碱性未被氨基基团上的取代基掩盖）或其盐。还公开了一种生产由通式（3）表示的具有光学活性的N-保护-S-苯基半胱氨酸或其盐的方法，其中包括将上述生产方法应用于光学活性丝氨酸或其盐，然后在碱性条件下进行氨基保护剂处理和与硫苯酚反应。

  公开号：

  US06372941B1

文献信息

• <i>Allium</i> Chemistry:  Synthesis, Natural Occurrence, Biological Activity, and Chemistry of <i>Se</i>-Alk(en)ylselenocysteines and Their γ-Glutamyl Derivatives and Oxidation Products
  作者：Eric Block、Marc Birringer、Weiqin Jiang、Tsukasa Nakahodo、Henry J. Thompson、Paul J. Toscano、Horst Uzar、Xing Zhang、Zongjian Zhu

  DOI：10.1021/jf001097b

  日期：2001.1.1

  selenocystine (4). Oxidation of 6d gives 2-[(E,Z)-1-propenylseleno]propanal (36). These oxidations occur by way of selenoxides, detected by chromatographic and spectroscopic methods. The natural occurrence of many of the Se-alk(en)ylselenocysteines and their gamma-glutamyl derivatives and oxidation products is discussed. Three homologues of the potent cancer chemoprevention agents 6a and 6c, namely

  据报道合成了γ-谷氨酰基Se-甲基硒代半胱氨酸（Sa），硒代羊毛硫氨酸（16），Se-1-丙烯基硒代半胱氨酸（Gd），Se-2-甲基-2-丙烯基-L-硒代半胱氨酸（6e）和Se-2-丙炔基-L-硒代半胱氨酸（6f）。8a和Se-甲基硒代半胱氨酸（Ga）的氧化得到甲烷硒酸（24）（通过X射线晶体学表征）和二甲基二硒化物（25）。Se-2-丙烯基-L-硒代半胱氨酸（6c）的氧化得到烯丙醇和3-硒代丙氨酸（22）。化合物22也会在16和硒代胱氨酸（4）氧化时形成。6d的氧化得到2-[（（E，Z）-1-丙烯基硒基]丙醛（36）。这些氧化通过亚硒酸盐发生，通过色谱法和光谱法检测。讨论了许多Se-alk（en）ylselenocysteines和它们的gamma-谷氨酰基衍生物和氧化产物的自然发生。使用两种鼠类乳腺上皮细胞系评估了三种有效的癌症化学预防剂6a和6c的同系物，即6d-f对细胞生长，细胞凋
• Influence of Sulfur‐Containing Diamino Acid Structure on Covalently Crosslinked Copolypeptide Hydrogels
  作者：Eric D. Raftery、Eric G. Gharkhanian、Nicole G. Ricapito、J. McNamara、Timothy J. Deming

  DOI：10.1002/asia.201801031

  日期：2018.11.16

  structure revealed that different di‐α‐amino acids were not equivalent in crosslink formation. Notably, l‐cystine was found to produce significantly weaker hydrogels compared to l‐homocystine, l‐cystathionine, and l‐lanthionine, suggesting that l‐cystine may be a sub‐optimal choice of di‐α‐amino acid for preparation of copolypeptide networks. The di‐α‐amino acid crosslinkers also provided different

  生物产生的非规范二α-氨基酸以合理的收率和高纯度转化为新的二氮-羧基酸酐（di-NCA）单体。五个不同的二种NCA分别用共聚叔丁基-升-谷氨酸NCA，以获得能够形成具有变化的密度的交联剂水凝胶的共价交联共聚。比较水凝胶性质和残基结构，发现不同的二-α-氨基酸在交联形成中不相等。值得注意的是，升-cystine发现相比以产生显著弱凝胶升-homocystine，升-cystathionine，和升-lanthionine，表明升在制备共肽网络时，胱氨酸可能不是最佳的二α-氨基酸选择。二α-氨基酸交联剂还提供不同的化学稳定性，其中二硫键容易被还原降解，硫醚交联对还原稳定。这种响应差异可以提供一种手段来微调多肽生物材料网络的还原敏感性。
• Synthesis of Novel Se-Substituted Selenocysteine Derivatives as Potential Kidney Selective Prodrugs of Biologically Active Selenol Compounds:  Evaluation of Kinetics of β-Elimination Reactions in Rat Renal Cytosol
  作者：Ioanna Andreadou、Wiro M. P. B. Menge、Jan N. M. Commandeur、Eduard A. Worthington、Nico P. E. Vermeulen

  DOI：10.1021/jm950750x

  日期：1996.1.1

  Eighteen Se-substituted selenocysteine derivatives were synthesized as potential kidney selective prodrugs which can be activated by renal cysteine conjugate beta-lyase to selenium-containing chemoprotectants or antitumor agents. Selenocysteine derivatives with aliphatic and benzylic Se-substituents were synthesized by reducing selenocystine to selenocysteine followed by a reaction with the corresponding

  合成了十八种硒取代的硒代半胱氨酸衍生物，作为潜在的肾脏选择性前药，可以通过肾脏半胱氨酸共轭β-裂解酶将其激活为含硒的化学保护剂或抗肿瘤剂。通过将硒代半胱氨酸还原为硒代半胱氨酸，然后与相应的烷基和苄基卤化物反应，可以合成具有脂肪族和苄基硒取代基的硒代半胱氨酸衍生物。通过β-氯丙氨酸与取代的苯硒醇化合物反应合成具有芳香族Se取代基的硒代半胱氨酸衍生物，后者是通过用NaBH4还原取代的二苯二硒化物而形成的。研究了大鼠肾脏细胞溶胶中硒代半胱氨酸缀合物的β-消除反应的酶动力学参数（表观Km和Vmax）。结果表明，硒取代的L-硒代半胱氨酸结合物是肾半胱氨酸结合物β-裂合酶的极好底物，如表观Km低和Vmax值高所表明的。苄基取代的Se-共轭物似乎比苯基和烷基取代的Se-共轭物是更好的底物。相应的L-半胱氨酸S-缀合物太差，无法获得合适的酶动力学。最近，提出了通过肾脏半胱氨酸缀合物β-裂合酶局部激活半胱氨
• 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
• Reactivity of Selenocystine and Tellurocystine: Structure and Antioxidant Activity of the Derivatives
  作者：Kandhan Satheeshkumar、Saravanan Raju、Harkesh B. Singh、Ray J. Butcher

  DOI：10.1002/chem.201803776

  日期：2018.11.27

  these amino acids, i.e., oxidation of 5 and 6, has been performed at various pH values. Hydrogen peroxide was used as an oxidant and it was treated with 5 and 6 in excess in acidic and basic media. Compound 5, upon oxidation, afforded SeIV and SeVI products. Selenocysteic acid [HO3SeCH2CH(NH2)COOH] 9, a novel SeVI compound, was isolated and characterised by single‐crystal X‐ray diffraction studies. In

  已经制备了l-硒代胱氨酸（5）和l- tellurocystine（6），并且已经在各种pH值下进行了这些氨基酸的反应，即5和6的氧化。使用过氧化氢作为氧化剂，并在酸性和碱性介质中用过量的5和6处理过氧化氢。化合物5经氧化，得到Se IV和Se VI产物。Selenocysteic酸[HO 3 SECH 2 CH（NH 2）COOH] 9，一种新型的硒VI通过单晶X射线衍射研究对化合物进行了分离和表征。相比之下，l- tellurocystine在被H 2 O 2氧化后可得到Te II和Te IV产物。分离出两性离子有机碲酸（IV）[TeCl 3 CH 2 CH（NH 3）COOH] 13并通过NMR和IR光谱，质谱和元素分析对其进行表征。化合物13在正交晶空间群中结晶。l蛋氨酸胱氨酸，当被NaBH 4还原时产生所需的碲酸酯中间体，将其用溴乙酸捕获。此外，还合成了l和d碲半胱氨酸衍生物，[（RTECH

表征谱图