脯氨酰丙氨酸 | 6422-36-2

• 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: 脯氨酰丙氨酸
• 英文名称: L-prolyl-L-alanine
• 英文别名: prolyl‐alanine；H-Pro-Ala-OH；Pro-Ala；AP；(2S)-2-[[(2S)-pyrrolidin-1-ium-2-carbonyl]amino]propanoate
• CAS: 6422-36-2
• 化学式: C₈H₁₄N₂O₃
• 分子量: 186.211
• InChiKey: FELJDCNGZFDUNR-WDSKDSINSA-N

物化性质

• 熔点：
  232 °C
• 沸点：
  454.2±45.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)
• 溶解度：
  水（轻微，超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -15°C

SDS

---

Section 1. Chemical Product and Company Identification
L-Prolyl-L-alanine
Common Name/
Trade Name
Manufacturer
Commercial Name(s)
Synonym
Chemical Name
Chemical Family
L-Prolyl-L-alanine

---

Section 4. First Aid Measures
Eye Contact Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at
least 15 minutes. Get medical attention if irritation occurs.
Skin Contact Wash with soap and water. Cover the irritated skin with an emollient. Get medical attention if irritation develops.
Serious Skin Contact Not available.
Inhalation If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get
medical attention.
Serious Inhalation Not available.
Ingestion Do NOT induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an
unconscious person. If large quantities of this material are swallowed, call a physician immediately. Loosen tight
clothing such as a collar, tie, belt or waistband.
Serious Ingestion Not available.

---

Section 5. Fire and Explosion Data
Flammability of the Product May be combustible at high temperature.
Auto-Ignition Temperature Not available.
Flash Points Not available.
Flammable Limits Not available.
Products of Combustion These products are carbon oxides (CO, CO2), nitrogen oxides (NO, NO2...).
Fire Hazards in Presence of Slightly flammable to flammable in presence of heat.
Various Substances
Explosion Hazards in Presence Risks of explosion of the product in presence of mechanical impact: Not available.
Risks of explosion of the product in presence of static discharge: Not available.
of Various Substances
SMALL FIRE: Use DRY chemical powder.
Fire Fighting Media
and Instructions LARGE FIRE: Use water spray, fog or foam. Do not use water jet.
As with most organic solids, fire is possible at elevated temperatures
Special Remarks on
Fire Hazards
Special Remarks on Explosion Not available.
Hazards

---

Section 6. Accidental Release Measures
Small Spill Use appropriate tools to put the spilled solid in a convenient waste disposal container. Finish cleaning by
spreading water on the contaminated surface and dispose of according to local and regional authority
requirements.
Large Spill Use a shovel to put the material into a convenient waste disposal container. Finish cleaning by spreading water
on the contaminated surface and allow to evacuate through the sanitary system.
L-Prolyl-L-alanine

---

Section 7. Handling and Storage
Precautions Keep away from heat. Keep away from sources of ignition. Ground all equipment containing material. Do not
breathe dust. Keep away from incompatibles such as oxidizing agents, reducing agents, alkalis.
Storage Keep container tightly closed. Keep container in a cool, well-ventilated area. Do not store above 0°C (32°F).
Freeze

---

Section 8. Exposure Controls/Personal Protection
Engineering Controls Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below
recommended exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to
airborne contaminants below the exposure limit.
Personal Protection
Safety glasses. Lab coat. Dust respirator. Be sure to use an approved/certified respirator or equivalent. Gloves.
Personal Protection in Case of Splash goggles. Full suit. Dust respirator. Boots. Gloves. A self contained breathing apparatus should be used
a Large Spill to avoid inhalation of the product. Suggested protective clothing might not be sufficient; consult a specialist
BEFORE handling this product.
Exposure Limits Not available.

---

Section 9. Physical and Chemical Properties
Physical state and appearance Solid. Odor Not available.
Taste Not available.
Molecular Weight 186.21 g/mole
Color Not available.
pH (1% soln/water) Not available.
Boiling Point Not available.
Melting Point Not available.
Critical Temperature Not available.
Not available.
Specific Gravity
Vapor Pressure Not applicable.
Vapor Density Not available.
Volatility Not available.
Odor Threshold Not available.
Not available.
Water/Oil Dist. Coeff.
Ionicity (in Water) Not available.
Not available.
Dispersion Properties
Solubility Not available.

---

Section 10. Stability and Reactivity Data
Stability The product is stable.
Not available.
Instability Temperature
Conditions of Instability Excess heat, incompatible materials.
Incompatibility with various Reactive with oxidizing agents, reducing agents, alkalis.
substances
Corrosivity Not available.
L-Prolyl-L-alanine
Special Remarks on Also incompatible with alkali metals.
Reactivity
Special Remarks on Not available.
Corrosivity
Polymerization Will not occur.

---

Section 11. Toxicological Information
Routes of Entry Inhalation. Ingestion.
Toxicity to Animals LD50: Not available.
LC50: Not available.
Chronic Effects on Humans Not available.
Other Toxic Effects on Slightly hazardous in case of skin contact (irritant), of ingestion, of inhalation.
Humans
Special Remarks on Not available.
Toxicity to Animals
Special Remarks on
Not available.
Chronic Effects on Humans
Special Remarks on other Acute Potential Health Effects:
Toxic Effects on Humans Skin: May cause skin irritation.
Eyes: May cause eye irritation.
Inhalation: Dust may cause respiratory tract irritation.
Ingestion: Expected to be a low hazard.

---

Section 12. Ecological Information
Ecotoxicity Not available.
BOD5 and COD Not available.
Products of Biodegradation Possibly hazardous short term degradation products are not likely. However, long term degradation products may
arise.
Toxicity of the Products The product itself and its products of degradation are not toxic.
of Biodegradation
Special Remarks on the Not available.
Products of Biodegradation

---

Section 13. Disposal Considerations
Waste Disposal Waste must be disposed of in accordance with federal, state and local environmental
control regulations.

---

Section 14. Transport Information
DOT Classification Not a DOT controlled material (United States).
Identification Not applicable.
Special Provisions for Not applicable.
Transport
L-Prolyl-L-alanine
DOT (Pictograms)

---

Section 15. Other Regulatory Information and Pictograms
No products were found.
Federal and State
Regulations
California California prop. 65: This product contains the following ingredients for which the State of California has found
to cause cancer which would require a warning under the statute: No products were found.
Proposition 65
Warnings
California prop. 65: This product contains the following ingredients for which the State of California has found
to cause birth defects which would require a warning under the statute: No products were found.
Other Regulations EINECS: This product is not on the European Inventory of Existing Commercial Chemical Substances.
Canada: Not listed on Canadian Domestic Substance List (DSL) or Canadian Non- Domestic Substance List
(NDSL).
China: Not listed on National Inventory.
Japan: Not listed on National Inventory (ENCS).
Korea: Not listed on National Inventory (KECI).
Philippines: Not listed on National Inventory (PICCS).
Australia: Not listed on AICS.
Other Classifications WHMIS (Canada) Not controlled under WHMIS (Canada).
DSCL (EEC) This product is not classified according Not applicable.
to the EU regulations.
Health Hazard
HMIS (U.S.A.) 1 National Fire Protection
1 Flammability
1 Association (U.S.A.)
Fire Hazard
1 0 Reactivity
Health
Reactivity
0
Specific hazard
Personal Protection
E
WHMIS (Canada)
(Pictograms)
DSCL (Europe)
(Pictograms)
TDG (Canada)
(Pictograms)
ADR (Europe)
(Pictograms)
Protective Equipment
Gloves.
L-Prolyl-L-alanine
Lab coat.
Dust respirator. Be sure to use an
approved/certified respirator or
equivalent.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  脯氨酰丙氨酸 以 乙酸乙酯 为溶剂， 生成 (3S,8aS)-六氢-3-甲基吡咯并[1,2-a]吡嗪-1,4-二酮
  参考文献：
  名称：

  Chemical Characterization of Diketopiperazines in Beer

  摘要：

  Diketopiperazines (DKPs) corresponding to cyclic dipeptides have been detected in a variety of natural products as well as in processed foods, beverages, and food and beverage ingredients. A series of seven proline-based diketopiperazines, namely, cyclo(Ala-Pro), cyclo(Val-Pro), cyclo(Ile-Pro), cyclo(Leu-Pro), cyclo(Met-Pro), cyclo(Phe-Pro), and cyclo(Pro-Pro), has now been identified in beer. A marketplace cross-section of five commercial beers was studied, involving products manufactured in different countries using distinctly different raw materials and brewing styles; maximum concentrations of individual diketopiperazines in various beers ranged from below detection limit to approximately 24 ppm. The flavor characteristics of these compounds were described variously as bitter, mouth coating, drying, astringent, salty, metallic, and grainy when evaluated in water at concentrations ranging fi om 10 to 50 ppm. However, it is questionable whether or not the diketopiperazines reported here make a significant contribution to either the aroma or taste of most beers.

  DOI：

  10.1021/jf9700992
• 作为产物：
  描述：

  Z-Pro-Ala 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 以94%的产率得到脯氨酰丙氨酸
  参考文献：
  名称：

  Tomida, Ichiro; Kimura, Yoichi; Kudo, Ikuko, Agricultural and Biological Chemistry, 1985, vol. 49, # 2, p. 529 - 532

  摘要：

  DOI：
• 作为试剂：
  描述：

  异戊醛 在 脯氨酰丙氨酸 N-氯代丁二酰亚胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以61%的产率得到
  参考文献：
  名称：

  [EN] CATALYTIC ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE alpha-HALO-CARBONYL COMPOUNDS
  [FR] SYNTHESE ASYMETRIQUE CATALYTIQUE DE COMPOSES DE DOLLAR G(A)-HALO-CARBONYLE OPTIQUEMENT ACTIFS

  摘要：

  一种用于催化不对称合成光学活性化合物的方法，其化学式为(la)或(lb)：其中R是有机基团；X是卤素；R1和R2可以相同也可以不同，分别代表H，或者是有机基团，或者R1和R2可以通过形成环系统的桥连接在一起；R和R2可以通过形成环系统的桥连接在一起；在R和R1不同且R2与H不同时通过碳-碳键连接时，包括以下步骤：将化合物(2)与卤化试剂在含有含有手性氮的有机化合物的催化剂量的情况下反应。

  公开号：

  WO2005080298A1

文献信息

• Electron spin resonance of spin trapped radicals in γ-irradiated polycrystalline dipeptides. Chromatographic separation of radicals
  作者：Keisuke Makino、Peter Riesz

  DOI：10.1139/v82-214

  日期：1982.6.15

  Polycrystalline dipeptides (glycyl-glycine, glycyl-L-valine, glycyl-L-leucine, L-alanyl-glycine, and L-prolyl-L-alanine) were γ-irradiated at room temperature in the absence of air. Subsequently they were dissolved in aqueous solutions containing 2-methyl-2-nitrosopropane as the spin trap. From the esr spectra of the nitroxide radicals separated by high-performance liquid chromatography, structural assignments of the radicals were made. For glycyl peptides, H-abstraction from the α-carbon atoms of the carboxyl terminal residues and from the side-chains were observed. For L-alanyl-glycine, H-abstraction from the glycyl residue and the formation of the deamination radical could be shown to occur. For L-prolyl-L-alanine, the ring opening (deamination) reaction, decarboxylation and H-abstraction from the C-terminal a-carbon were seen.

  多晶二肽（甘氨酸-甘氨酸，甘氨酸-L-缬氨酸，甘氨酸-L-亮氨酸，L-丙氨酰-甘氨酸和L-脯氨酰-L-丙氨酸）在室温下在无空气的情况下进行γ辐照。随后，它们被溶解在含2-甲基-2-亚硝基丙烷作为自旋陷阱的水溶液中。通过高效液相色谱分离的亚硝基自由基的esr光谱，对自由基的结构进行了确定。对于甘氨酸肽，观察到了从羧基末端残基的α-碳原子和侧链中的氢抽取。对于L-丙氨酰-甘氨酸，可以显示从甘氨酸残基中抽取氢和形成去氨基自由基的反应发生。对于L-脯氨酰-L-丙氨酸，观察到了环开启（去氨基）反应，脱羧和从C-末端α-碳中的氢抽取。
• Elektrochemische Decarboxylierung vonL.-Threonin- und Oligopeptid-Derivaten unter Bildung vonN-Acyl-N, O-acetalen: Herstellung von Oligopeptiden mit Carboxamid-oder Phosphonat-C-Terminus
  作者：Dieter Seebach、Roland Charczuk、Christian Gerber、Philippe Renaud、Heinz Berner、Helmut Schneider

  DOI：10.1002/hlca.19890720302

  日期：1989.5.3

  Electrochemical Decarboxylation of L-Threonine and Oligopeptide Derivatives with Formation of N-Acyl-N, O-acetals: Preparation of Oligopeptides with Amide or Phophonate C-Terminus

  L-苏氨酸和寡肽衍生物的电化学脱羧反应，形成N-酰基-N，O-乙缩醛：酰胺或膦C-末端制备寡肽
• PROCESSES FOR PREPARING JAK INHIBITORS AND RELATED INTERMEDIATE COMPOUNDS
  申请人：Zhou Jiacheng

  公开号：US20100190981A1

  公开（公告）日：2010-07-29

  The present invention is related to processes for preparing chiral substituted pyrazolyl pyrrolo[2,3-d]pyrimidines of Formula III, and related synthetic intermediate compounds. The chiral substituted pyrazolyl pyrrolo[2,3-d]pyrimidines are useful as inhibitors of the Janus Kinase family of protein tyrosine kinases (JAKs) for treatment of inflammatory diseases, myeloproliferative disorders, and other diseases.

  本发明涉及制备手性取代吡唑基吡咯并[2,3-d]嘧啶的公式III的过程，以及相关的合成中间体化合物。这些手性取代吡唑基吡咯并[2,3-d]嘧啶可用作抑制Janus激酶家族蛋白酪氨酸激酶（JAKs）的药物，用于治疗炎症性疾病、骨髓增生性疾病和其他疾病。
• [EN] PROCESSES FOR PREPARING JAK INHIBITORS AND RELATED INTERMEDIATE COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION D'INHIBITEURS DES JAK ET COMPOSÉS INTERMÉDIAIRES APPARENTÉS
  申请人：INCYTE CORP

  公开号：WO2010083283A2

  公开（公告）日：2010-07-22

  The present invention is related to processes for preparing chiral substituted pyrazolyl pyrrolo[2,3-di]pyrimidines of Formula III, and related synthetic intermediate compounds. The chiral substituted pyrazolyl pyrrolo[2,3-d]pyrimidines are useful as inhibitors of the Janus Kinase family of protein tyrosine kinases (JAKs) for treatment of inflammatory diseases, myeloproliferative disorders, and other diseases.

  本发明涉及制备手性取代的Formula III的吡唑基吡咯并[2,3-di]嘧啶化合物的过程，以及相关的合成中间体化合物。手性取代的吡唑基吡咯并[2,3-d]嘧啶化合物可用作Janus激酶家族的蛋白酪氨酸激酶（JAKs）的抑制剂，用于治疗炎症性疾病、骨髓增生性疾病和其他疾病。
• Aryloxy and arylacyloxy methyl ketones as thiol protease inhibitors
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05158936A1

  公开（公告）日：1992-10-27

  Thiol protease inhibitors are disclosed having the formula: ##STR1## or an optical isomer thereof, or a pharmaceutically acceptable salt thereof, wherein: n is 0 or 1; m is 0, 1 or 2; X is H or an N-protecting group; each Y is independently an optionally protected .alpha.-amino acid residue; R is an optionally protected .alpha.-amino acid side chain that is H or CH.sub.3 or that is bonded to the .alpha.-carbon atom to which it is attached by a methylene, methine or phenyl radial; and R' is optionally substituted aryl.

  本发明披露了具有以下式子的硫醇蛋白酶抑制剂：##STR1## 或其光学异构体，或其药学上可接受的盐，其中：n为0或1；m为0、1或2；X为H或N-保护基；每个Y独立地是一个可选保护的α-氨基酸残基；R是可选保护的α-氨基酸侧链，其为H或CH.sub.3或通过亚甲基、亚胺基或苯基辐射与其连接的α-碳原子相结合；R'为可选取代的芳基。

表征谱图