D-半胱氨酸 | 921-01-7

• 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: D-半胱氨酸
• 中文别名: D-氨基-3-巯基丙酸；(S)-2-氨基-3-巯基丙酸
• 英文名称: cysteine
• 英文别名: (2S)-2-ammonio-3-mercaptopropanoate；(2S)-2-azaniumyl-3-sulfanylpropanoate
• CAS: 921-01-7
• 化学式: C₃H₇NO₂S
• 分子量: 121.16
• InChiKey: XUJNEKJLAYXESH-UWTATZPHSA-N

物化性质

• 熔点：
  ~230 °C (dec.)
• 沸点：
  293.9±35.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于酸性水溶液（轻微）、水（轻微）
• LogP：
  0.230 (est)
• 物理描述：
  Solid
• 颜色/状态：
  Colorless crystals
• 蒸汽压力：
  6.73X10-7 mm Hg at 25 °C (est)
• 稳定性/保质期：

  在常温常压下稳定。

• 旋光度：
  Specific optical rotation: +6.5 deg at 25 °C/D (5 N HCl); +13.0 deg at 25 °C/D (glacial acetic acid)
• 分解：
  When heated to decomposition it emits very toxic fumes of /sulfur oxides and nitrogen oxides/.
• 解离常数：
  pK1 1.71 /carboxylic/; pK2 8.33 /amine/; pK3 10.78 /sulfide/

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 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：
  64.3
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29309013
• 危险品运输编号：
  NONH for all modes of transport
• 危险标志：
  GHS07
• 危险性描述：
  H302
• 危险性防范说明：
  P501,P270,P264,P301+P312+P330

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: D-Cysteine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
P264: Wash thoroughly after handling
P270: Do not eat, drink or smoke when using this product
P301+P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
P330: Rinse mouth

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Section 3. Composition/information on ingredients.
Ingredient name: D-Cysteine
CAS number: 921-01-7

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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
This product should be handled only by, or under the close supervision of, those properly qualified
Handling:
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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C3H7NO2S
Molecular weight: 121.2

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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, sulfur 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

生物活性

D-丙氨酸是一种半胱氨酸的D型异构体，也是大肠杆菌生长的有效抑制剂。它通过D-氨基酸氧化酶产生H2S，并且能够作为针对小脑共济失调的神经保护剂。此外，D-丙氨酸可以抑制由变形链球菌和血红链球菌形成的双物种生物膜的生长和致龋性。

靶点

Human 内源性代谢物

用途

用于有机合成

反应信息

• 作为反应物：
  描述：

  D-半胱氨酸 生成 L-胱氨酸
  参考文献：
  名称：

  PREMAZZI, G.;BUONACCORSI, G.;ZILIO, P., WATER RES., 23,(1989) N, C. 431-442

  摘要：

  DOI：
• 作为产物：
  描述：

  L-噻唑烷-4-羧酸 生成 D-半胱氨酸
  参考文献：
  名称：

  SHIRAIWA, TADASHI;KATAOKA, KAZUO;SAKATA, SHINJI;KUROKAWA, HIDEMOTO, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 109-113

  摘要：

  DOI：

文献信息

• A Semisynthetic Strategy Leads to Alteration of the Backbone Amidate Ligand in the NiSOD Active Site
  作者：Julius O. Campeciño、Lech W. Dudycz、David Tumelty、Volker Berg、Diane E. Cabelli、Michael J. Maroney

  DOI：10.1021/jacs.5b03629

  日期：2015.7.22

  reveals a four-coordinate planar site with N2S2-donor ligands, consistent with electronic absorption spectroscopic results indicating that the Ni center in H1*-NiSOD is mostly reduced in the as-isolated sample, as opposed to 50:50 Ni(II)/Ni(III) mixture that is typical for the recombinant wild-type enzyme. The EPR spectrum of as-isolated H1*-NiSOD accounts for ∼11% of the Ni in the sample and is similar

  计算研究表明，镍超氧化物歧化酶 (NiSOD) 中的酰胺配体在稳定以 Ni 为中心的氧化还原催化和防止半胱氨酸硫醇盐配体氧化方面发挥了重要作用。为了测试这些预测，我们使用了一种利用半合成方案的实验方法，该方案采用五肽 (HCDLP) 的天然化学连接与缺乏这些 N 末端残基 NΔ5-NiSOD 的重组天蓝色 NiSOD。以这种方式产生的野生型酶表现出重组 WT-NiSOD 的特征光谱特性，并且具有催化活性。半合成方案也被用于构建一个变体，其中酰胺配体被转化为仲胺，H1*-NiSOD，这是一种保留主链 N-供体原子的新策略。发现 H1*-NiSOD 变体的催化活性仅为重组野生型酶的约 1%，并且具有改变的光谱特性。X 射线吸收光谱揭示了一个带有 N2S2 供体配体的四坐标平面位点，与电子吸收光谱结果一致，表明 H1*-NiSOD 中的 Ni 中心在分离的样品中大部分减少，而不是 50:50 Ni(II)/Ni(III)
• Differences in heterocycle basicity distinguish homocysteine from cysteine using aldehyde-bearing fluorophores
  作者：Aabha Barve、Mark Lowry、Jorge O. Escobedo、Katherine T. Huynh、Lovemore Hakuna、Robert M. Strongin

  DOI：10.1039/c4cc03527e

  日期：——

  Homocysteine reacts with aldehyde-derived fluorescein to form thiazinane. Controlled protonation of the thiazinane amine leads to fluorescence enhancement, thus distinguishing homocysteine from cysteine.

  同型半胱氨酸与醛衍生的荧光素反应形成噻嗪环。对噻嗪环胺的控制质子化导致荧光增强，从而区分同型半胱氨酸和半胱氨酸。
• 玛咖素A衍生物的合成制备方法和应用
  申请人：云南民族大学

  公开号：CN107056818A

  公开（公告）日：2017-08-18

  本发明公开了一种玛咖素A衍生物 (I和II) 的合成制备方法和应用，其合成路线为：所述的玛咖素A衍生物为玛咖素A的合成类衍生物 (I和II)，英文名为meyeniin A derivatives，该类化合物是以从药用植物玛咖中分离得到的新颖天然生物碱meyeniin A为模板，以前体半胱氨酸为起始原料，通过两步化学反应合成得到的一系列人工类似物，其基本结构特点是由一个六氢咪唑[1,5‑c]噻唑母核和一个不同取代基的苄基取代基组成，其侧链取代基上不同取代基决定了这类化合物的多样性。本发明的玛咖素A的合成类衍生物均为首次合成，且部分衍生物具有潜在的生物活性，可作为抗肿瘤药物的先导化合物，有一定的研究价值和应用前景。
• Resolution of amino acids
  申请人：Yeda Research and Development Company Ltd.

  公开号：US04390722A1

  公开（公告）日：1983-06-28

  A process for resolution of a mixture of D- and L- amino acids, selected from threonine (THR), asparagine (ASN), p-hydroxyphenylglycine p-toluene sulfonate (pHPGpTS) and glutamic acid hydrochloride (GLU), which crystallize in the form of a conglomerate, whereby the ratio of one desired enantiomorph to the other undesired enantiomorph of said amino acid is increased in the crystalline compound obtained, as compared to the ratio in the starting material, which process comprises forming a supersaturated solution of said mixture, adding another predetermined amino acid as additive, which has a molecular structure which resembles that of one of the enantiomers of said racemic mixture, said additive being a D-amino acid as an inhibitor of the growing D-amino acid when the L-amino acid is desired, or a L-amino acid when the D-amino acid is desired, and crystallizing part of the compound from said supersaturated solution. When GLU.HCl is resolved, the crystals can be separated as they have different morphological forms.

  一种处理D-和L-氨基酸混合物的方法，所选氨基酸为苏氨酸（THR），天冬酰胺（ASN），对羟基苯甘氨基对甲苯磺酸盐（pHPGpTS）和盐酸谷氨酸（GLU），它们以聚集体的形式结晶，通过该方法，与起始材料中的比率相比，所得到的晶体化合物中所需对映异构体与其他不需要的对映异构体的比率增加，该方法包括形成所述混合物的过饱和溶液，添加另一种预定的氨基酸作为添加剂，该添加剂具有与所述混合物的一种对映异构体的分子结构相似的结构，当需要L-氨基酸时，该添加剂是D-氨基酸作为抑制剂，抑制D-氨基酸的生长，或者当需要D-氨基酸时，该添加剂是L-氨基酸，然后从所述过饱和溶液中结晶化合物的一部分。当GLU.HCl被分解时，晶体可分离，因为它们具有不同的形态。
• Analogues of thiocoraline and be-22179
  申请人：——

  公开号：US20040072738A1

  公开（公告）日：2004-04-15

  A process for the total synthesis of thiocoraline and BE-22179 establishes the relative and absolute stereochemistry of these compounds and enables the construction and characterization of a series of related analogues. The mechanism for the bioactivity of thiocoraline, BE-22179 and their related analogues is charaterized. Thiocoraline, BE-22179, and their related analogues are disclosed to bind to DNA by high-affinity bisintercalation and are disclosed to exhibit exceptional cytotoxic activity.

  一种用于全合成thiocoraline和BE-22179的过程，确定了这些化合物的相对和绝对立体化学，并能够构建和表征一系列相关的类似物。确定了thiocoraline、BE-22179及其相关类似物的生物活性机制。披露了thiocoraline、BE-22179及其相关类似物通过高亲和力双插入结合到DNA，并表现出异常的细胞毒性活性。

表征谱图