L-磺基丙氨酸 | 498-40-8

• 物质功能分类: 生物化工 - 常见氨基酸及蛋白质类
• 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: L-磺基丙氨酸
• 中文别名: 磺基丙氨酸；3-磺基-L-丙氨酸
• 英文名称: L-Cysteic acid
• 英文别名: cysteic acid；Cysteinsaeure；L-Cysteinsaeure；(2R)-2-amino-3-sulfopropanoic acid
• CAS: 498-40-8
• 化学式: C₃H₇NO₅S
• mdl: MFCD00007524
• 分子量: 169.158
• InChiKey: XVOYSCVBGLVSOL-REOHCLBHSA-N

物化性质

• 熔点：
  260℃ (dec.)
• 比旋光度：
  [α]D20 +7.5～+9.5° (c=7.4, H2O)
• 密度：
  1.775±0.06 g/cm3(Predicted)
• 溶解度：
  甲醇（微溶）、水（微溶）
• 碰撞截面：
  120.55 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]
• 稳定性/保质期：

  按规格使用和贮存，不会发生分解，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 安全说明：
  S26,S36
• 危险类别码：
  R36/38
• 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：
  密封保存，并放置在通风、干燥的环境中。

SDS

L-Cysteic Acid Revision number: 1
SAFETY DATA SHEET

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Section 1. BASE INFORMATION
Product name: L-Cysteic Acid

Revision number: 1

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Section 2. HAZARDS IDENTIFICATION
Classification of the GHS
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS Not classified
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements
None
Pictograms or hazard symbols
Signal word No signal word
None
Hazard statement
Precautionary statements None

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Component(s): L-Cysteic Acid
Percent: >98.0%(T)
CAS Number: 498-40-8
Chemical Formula: C3H7NO5S

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards: Take care as it may decompose upon combustion or in high temperatures to
generate poisonous fume.
Specific methods: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
L-Cysteic Acid

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Section 5. FIRE-FIGHTING MEASURES
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Storage
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Law is followed.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Protective gloves.
Hand protection:
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: crystal - powder
White - Almost white
Color:
Odor: No data available
pH: No data available
Melting point/freezing point:No data available
Boiling Point/Range: No data available
Flash Point: No data available
Explosive limits
Lower: No data available
No data available
Upper:
Density: No data available
No data available
Solubility:

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Section 10. STABILITY AND REACTIVITY
Stability: Stable under proper conditions.
Reactivity: No special reactivity has been reported.
Incompartible materials: oxidizing agents
Hazardous Decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Sulphur oxides
Products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
L-Cysteic Acid

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Section 11. TOXICOLOGICAL INFORMATION
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
No data available
IARC =
NTP = No data available
No data available
Reproductive toxicity:

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobillity in soil
log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not Listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26,
2002): Safe use and production, the storage of a dangerous chemical, transport, loading and unloading were
prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

合成制备方法

将胱氨酸溶于稀盐酸，滴加溴，反应液温度升至约60℃。在减压下蒸发后，将剩余物溶于蒸馏水中，滤去不溶物。滤液浓缩冷却结晶后过滤，用乙醇洗涤滤饼并干燥，得到L-磺基丙氨酸，产率为81-90%。

用途

用于有机合成。

反应信息

• 作为反应物：
  描述：

  L-磺基丙氨酸 生成 牛磺酸
  参考文献：
  名称：

  Sloane-Stanley, Biochemical Journal, 1949, vol. 45, p. 557

  摘要：

  DOI：
• 作为产物：
  描述：

  L-胱氨酸 在 溴 作用下， 生成 L-磺基丙氨酸
  参考文献：
  名称：

  The Crystal Structure ofl-Cysteic Acid

  摘要：

  半胱氨酸 C3H7NO5S 的晶体结构已经确定。该晶体为正菱形，空间群为 P212121，四个分子位于一个单位晶胞中，其尺寸分别为：a=8.35、b=10.16 和 c=7.44 Å。该分子为齐聚离子 -O3SCH2CH-(NH3+)COOH；其尺寸与其他氨基酸和磺酸的尺寸基本相似。酸性基团占据 Cα-Cβ 键的反式位置，而氨基则处于磺酸基团的顺式位置，并在它们之间形成分子内氢键。

  DOI：

  10.1246/bcsj.41.2305

文献信息

• Synthesis of Sulfonyl Chlorides and Sulfonic Acids in SDS Micelles
  作者：Kiumars Bahrami、Mohammad Khodaei、Jamshid Abbasi

  DOI：10.1055/s-0031-1289628

  日期：2012.1

  direct oxidative chlorination of thiol and di­sulfide derivatives to give the desired sulfonyl chlorides. The oxidation of thiols and disulfides to sulfonic acids with this system is also reported. In most cases, these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity. micelles - oxidation - hydrogen peroxide - thiols - solvent systems - amphiphiles

  发现H 2 O 2 / POCl 3是一种反应性试剂体系，可以在水性介质中的十二烷基硫酸钠（SDS）胶束溶液中使用，用于硫醇和二硫键衍生物的直接氧化氯化，得到所需的磺酰氯。还报道了用该系统将硫醇和二硫化物氧化为磺酸。在大多数情况下，这些反应具有高度的选择性，简单性和清洁性，可提供具有优异收率和高纯度的产品。 胶束-氧化-过氧化氢-硫醇-溶剂系统-两亲物
• Oxidation of thiols by superoxide ion
  作者：G Crank、MIH Makin

  DOI：10.1071/ch9842331

  日期：——

  Superoxide ion oxidizes aromatic thiols to disulfides or sulfonic acids. Benzene-1,2-dithiol and its 4-methyl analogue formed the cyclic disulfides dibenzo[c,g]tetrathiocins. Aliphatic thiols gave disulfides, and ethane-1,2-dithiol and propane-1,3-dithiol formed the cyclic disulfides 1,2,5,6- tetrathiocan and 1,2,6,7-tetrathiecan respectively. Butane-1,4-dithiol underwent an intramolecular cyclization to 1,2-dithian. Cysteine was oxidized by O2-· to cysteic acid.

  超氧离子可将芳香族硫醇氧化为二硫化物或磺酸。苯-1,2-二硫醇及其 4-甲基类似物形成环状二硫化物二苯并[c,g]四硫辛酸。脂肪族硫醇产生 二硫化物，乙烷-1,2-二硫醇和丙烷-1,3-二硫醇形成环状二硫化物 1,2,5,6- 和 1,2,6,7-Tetrathiecan 的环状二硫化物。1,2,5,6-四硫杂环烷和 1,2,6,7-四硫杂环烷。 环化成 1,2-二硫杂环。半胱氨酸被 O2 氧化成半胱氨酸。
• [EN] HYDRAZINYL-PYRROLO COMPOUNDS AND METHODS FOR PRODUCING A CONJUGATE<br/>[FR] COMPOSÉS HYDRAZINYL-PYRROLO ET PROCÉDÉS DE PRODUCTION D'UN CONJUGUÉ
  申请人：REDWOOD BIOSCIENCE INC

  公开号：WO2015081282A1

  公开（公告）日：2015-06-04

  The present disclosure provides conjugate structures and hydrazinyl-pyrrolo compound structures used to produce these conjugates. The disclosure also encompasses methods of production of such conjugates, as well as methods of using the same. Aspects of the present disclosure include a pharmaceutical composition. The pharmaceutical composition includes a conjugate as described herein and a pharmaceutically acceptable excipient. Aspects of the present disclosure include a method of delivering a conjugate to a subject. The method includes administering to the subject an effective amount of a conjugate as described herein. Aspects of the present disclosure include a method of treating a condition in a subject.

  本公开提供用于生产这些共轭物的共轭结构和肼基吡咯烷化合物结构。该公开还涵盖了生产这种共轭物的方法，以及使用相同的方法。本公开的方面包括一种药物组合物。该药物组合物包括本文所述的共轭物和药用可接受的赋形剂。本公开的方面包括将共轭物输送给受试者的方法。该方法包括向受试者施用本文所述的共轭物的有效量。本公开的方面包括治疗受试者病症的方法。
• Tetrahydroimidazo[1,2‐ <i>a</i> ]pyrazine Derivatives: Synthesis and Evaluation as Gα _q ‐Protein Ligands
  作者：Jim Küppers、Tobias Benkel、Suvi Annala、Kenichi Kimura、Lisa Reinelt、Bernd K. Fleischmann、Evi Kostenis、Michael Gütschow

  DOI：10.1002/chem.202001446

  日期：2020.10

  The 5,6,7,8‐tetrahydroimidazo[1,2‐a]pyrazine derivative BIM‐46174 and its dimeric form BIM‐46187 (1) are heterocyclized dipeptides that belong to the very few cell‐permeable compounds known to preferentially silence Gαq proteins. To explore the chemical space of Gαq inhibitors of the BIM chemotype, a combinatorial approach was conducted towards a library of BIM molecules. This library was evaluated

  5,6,7,8-四氢咪唑并[1,2- a ]吡嗪衍生物 BIM-46174 及其二聚体形式 BIM-46187 ( 1 ) 是杂环化二肽，属于极少数已知优先沉默 Gα 的细胞渗透性化合物q蛋白。为了探索 BIM 化学型 Gα q抑制剂的化学空间，对 BIM 分子库进行了组合方法。该文库在基于第二信使的荧光测定中进行了评估，通过测定细胞内肌醇1-磷酸来分析 Gα q蛋白的活性。推导了结构-活性关系并获得了生物活性的结构要求，它们是（i）氧化还原反应性硫醇/二硫烷子结构，（ii）N-末端碱性氨基，（iii）环己基丙氨酸部分，和（iv）双环骨架。活性化合物表现出细胞毒性，对此原型抑制剂进行了详细研究1。该化合物以 Gα q/11独立的方式影响结构细胞骨架动力学。
• Sulfonate derived phosphoramidates as active intermediates in the enzymatic primer-extension of DNA
  作者：S. De、E. Groaz、L. Margamuljana、M. Abramov、P. Marlière、P. Herdewijn

  DOI：10.1039/c5ob00157a

  日期：——

  The incorporation and extension of synthetically unprecedented nucleoside phosphoramidate sulfonates is demonstrated using thermophilic and mesophilic microbial polymerases.

  使用嗜热和中温微生物聚合酶展示了合成前所未有的核苷酸磷酸酰胺磺酸盐的合并和扩展。

表征谱图