N-ALPHA-苄酰-L-精氨酸 | 154-92-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 精氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-ALPHA-苄酰-L-精氨酸
• 中文别名: N-α-苄基-L-精氨酸；N-a-苄基-L-精氨酸；NAlpha-苯甲酰-L-精氨酸；Nα-苯甲酰-L-精氨酸；N-α-苄基－L-精氨酸；N-α-苯甲酰-L-精氨酸；N-苯甲酰基-L-精氨酸；N-Α-苄基-L-精氨酸
• 英文名称: Nα-benzoyl-L-arginine
• 英文别名: Bz-Arg-OH；N-benzoyl-L-arginine；N^α-Benzoyl-L-arginin；(2S)-2-benzamido-5-(diaminomethylideneammonio)pentanoate；(2S)-2-benzamido-5-(diaminomethylideneazaniumyl)pentanoate
• CAS: 154-92-7
• 化学式: C₁₃H₁₈N₄O₃
• mdl: MFCD24743474
• 分子量: 278.311
• InChiKey: RSYYQCDERUOEFI-JTQLQIEISA-N

物化性质

• 熔点：
  281-286 °C
• 沸点：
  421.13°C (rough estimate)
• 密度：
  1.1713 (rough estimate)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 安全说明：
  S22,S24/25
• 危险类别码：
  R20/21/22
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  0-6°C

SDS

Name:	N-Alpha-Benzoyl-l-Arginine 99% Material Safety Data Sheet
Synonym:	None
CAS:	154-92-7

Section 1 - Chemical Product MSDS Name:N-Alpha-Benzoyl-l-Arginine 99% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
154-92-7	N-alpha-benzoyl-l-arginine	99.0	205-837-7

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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.
Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Remove contaminated clothing and shoes.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid. Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 154-92-7: Personal Protective Equipment Eyes: Wear chemical splash goggles. Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin. Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 285 deg C
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: C13H18N4O3
Molecular Weight: 278.30

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 154-92-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N-alpha-benzoyl-l-arginine - 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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 154-92-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 154-92-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 154-92-7 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

用途：用作生化试剂

反应信息

• 作为反应物：
  描述：

  N-ALPHA-苄酰-L-精氨酸 在 乙酸酐 、 溶剂黄146 作用下， 生成 5-[[氨基(亚氨基)甲基]氨基]-2-(苄氨基)戊酸
  参考文献：
  名称：

  Kitagawa; Izumiya, Journal of Biochemistry, 1959, vol. 46, p. 1159,1161

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苯甲酰基-L-精氨酸乙酯盐酸盐 在 L-1,4-二硫代苏糖醇 、 水 、 papain 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.08h， 生成 N-ALPHA-苄酰-L-精氨酸
  参考文献：
  名称：

  Synthesis of papain–polyacrylamide hydrogel microspheres and their catalytic application

  摘要：

  一个形成木瓜蛋白酶-PAHMs的过程示意图。

  DOI：

  10.1039/d1nj02551a
• 作为试剂：
  描述：

  L-精氨酸 、 L-瓜氨酸 、 Nω-单甲基-L-精氨酸乙酸酯 、 (2S)-2-氨基-5-[(氨基-二甲基氨基甲基亚基)氨基]戊酸 、 对称N,N-二甲基精氨酸 、 在 乙酸乙酯 、 盐酸 、 N-ALPHA-苄酰-L-精氨酸 、 (2S)-2-氨基-5-[(氨基-二甲基氨基甲基亚基)氨基]戊酸 、 对称N,N-二甲基精氨酸 作用下， 以 碳酸氢钠 、 水 为溶剂， 反应 1.0h， 生成 N-ALPHA-苄酰-L-精氨酸
  参考文献：
  名称：

  Peptidyl Arginine Deiminase Type IV Inhibitor

  摘要：

  提供了由通式（I）表示的化合物或其盐： 其中，R1、R2和R3分别独立地表示氢原子或具有1至3个碳原子的烷基，但至少其中一个不表示氢原子；R4表示具有取代基的氨基；R5表示可能具有取代基的羧基。还提供了一种肽精氨酰基脱氨酶4抑制剂。该抑制剂可用于预防和/或治疗与肽精氨酰基脱氨酶相关的疾病（例如，类风湿性关节炎和多发性硬化症）。

  公开号：

  US20070276040A1

文献信息

• Synthetic Approaches to a Challenging and Unusual Structure—An Amino-Pyrrolidine Guanine Core
  作者：Rafael Rippel、Luís Pinheiro、Mónica Lopes、Ana Lourenço、Luísa M. Ferreira、Paula S. Branco

  DOI：10.3390/molecules25040797

  日期：——

  The synthesis of an unreported 2-aminopyrrolidine-1-carboxamidine unit is here described for the first time. This unusual and promising structure was attained through the oxidative decarboxylation of amino acids using the pair of reagents, silver(I)/peroxydisulfate (Ag(I)/S2O82−) followed by intermolecular (in the case of l-proline derivative) and intramolecular trapping (in the case of acyl l-arginine)

  此处首次描述了未报告的 2-氨基吡咯烷-1-甲脒单元的合成。这种不寻常且有前途的结构是通过使用一对试剂银（I）/过二硫酸盐（Ag（I）/S2O82-），然后是分子间（在 l-脯氨酸衍生物的情况下）和分子内的试剂对氨基酸进行氧化脱羧而获得的N-亲核试剂捕获（在酰基 l-精氨酸的情况下）。l-脯氨酸方法在合成 2-氨基吡咯烷-1-甲脒衍生物方面具有更广泛的范围，而由 l-酰基精氨酸提供的分子内环化在应用时会产生更高的产率。前者允许首次合成 cernumidine，一种于 2011 年从 Solanum cernuum Vell 中分离的天然生物碱，作为其外消旋形式。
• [EN] COMPOUNDS USEFUL FOR THE TREATMENT AND/OR CARE OF THE SKIN, HAIR, NAILS AND/OR MUCOUS MEMBRANES<br/>[FR] COMPOSÉS UTILES DANS LE TRAITEMENT ET/OU LES SOINS DE LA PEAU, DES CHEVEUX, DES ONGLES ET/OU DES MUQUEUSES
  申请人：LUBRIZOL ADVANCED MAT INC

  公开号：WO2019008452A1

  公开（公告）日：2019-01-10

  A compound of formula (I) R1-Wm-Xn-AA1-AA2-AA3-AA4-AA5-AA6-AA7-AA8-AA9-Yp-Zq-R2 wherein AA1 is Phe; AA2 is Trp; AA3 is selected from the group consisting of Met, Leu and lie; AA4 is selected from the group consisting of Lys, Arg and Gin; AA5 is Arg; AA6 is Lys; AA7 is selected from the group consisting of Arg, Lys and His; AA8 is selected from the group consisting of Val, lie, Leu and Met; and AA9 is Pro, useful in the treatment and/or care of the skin, hair, nails and/or mucous membranes, in particular for improving the barrier function of the skin, for energising the skin and as an anti- aging agent.

  一种具有以下结构的化合物（I）R1-Wm-Xn-AA1-AA2-AA3-AA4-AA5-AA6-AA7-AA8-AA9-Yp-Zq-R2，其中AA1为Phe；AA2为Trp；AA3选自Met、Leu和Ile组成的群体；AA4选自Lys、Arg和Gln组成的群体；AA5为Arg；AA6为Lys；AA7选自Arg、Lys和His组成的群体；AA8选自Val、Ile、Leu和Met组成的群体；AA9为Pro。该化合物在治疗和/或护理皮肤、头发、指甲和/或粘膜方面具有用途，特别用于改善皮肤的屏障功能，激活皮肤并作为抗衰老剂。
• [EN] POLYSUBUNIT OPIOID PRODRUGS RESISTANT TO OVERDOSE AND ABUSE<br/>[FR] PROMÉDICAMENTS D'OPIOÏDES À SOUS-UNITÉS MULTIPLES RÉSISTANTS AUX SURDOSES ET AUX ABUS
  申请人：ELYSIUM THERAPEUTICS INC

  公开号：WO2018170465A1

  公开（公告）日：2018-09-20

  The invention provides compositions and methods for the treatment or prevention of pain. Compositions provided are resistant to overdose and abuse. Compositions provided comprise two or more different molecules, where each molecule comprises at least one GI enzyme-labile opioid agonist releasing subunit comprising an opioid agonist that is covalently linked to at least one GI enzyme inhibitor subunit.

  这项发明提供了用于治疗或预防疼痛的组合物和方法。所提供的组合物具有抗过量和滥用的特性。所提供的组合物包括两种或两种以上不同的分子，其中每种分子至少包括一个至少含有一个胃肠酶敏感的阿片类受体激动剂释放亚基的阿片类受体激动剂，该阿片类受体激动剂与至少一个胃肠酶抑制剂亚基共价连接。
• Enzymes in organic synthesis: use of subtilisin and a highly stable mutant derived from multiple site-specific mutations
  作者：Chi Huey Wong、S. T. Chen、William J. Hennen、Jeffrey A. Bibbs、Y. F. Wang、Jennifer L. C. Liu、Michael W. Pantoliano、Marc Whitlow、Philip N. Bryan

  DOI：10.1021/ja00159a006

  日期：1990.1

  wild-type enzyme to organic synthesis has been demonstrated in the regioselective acylation of nucleosides in anhydrous dimethylformamide (with 65-100% regioselectivity at the 5'-position), in the enantioselective hydrolysis of N-protected and unprotected common and uncommon amino acid esters inmore » water (with 85-98% enantioselectivity for the L-isomer), and in the synthesis of di- and oligopeptides

  发现通过六个位点特异性突变（Met50Phe、Gly169Ala、Asn76Asp、Gln206Cys、Tyr2l7Lys 和 Asn2l8Ser）衍生自枯草杆菌蛋白酶 BPN' 的枯草杆菌蛋白酶突变体（枯草杆菌蛋白酶 8350）在水溶液中比野生溶液中的稳定性高 100 倍在无水二甲基甲酰胺中比野生型稳定 50 倍。使用酯、硫酯和酰胺底物以及过渡态类似物抑制剂 Boc-Ala-Val-Phe-CFsub 3} 的动力学研究表明，野生型和突变型酶具有非常相似的特异性和催化作用特性。野生型酶的抑制常数 (Ki = 5.0 mu}M) 是突变酶 (Ki = 1.1 mu}M) 的约 5 倍，表明突变酶与反应过渡态的结合比野生型酶。该结果与观察到的相应酯和酰胺底物的速率常数一致；即，突变体的 ksub cat}/Ksub m} 值大于野生型酶的值。突变酶和野生型酶在有机合成中的应用已在无
• MONITORED AMINOLYSIS OF 3-ACYL-l,3-THIAZ0LIDINE-2-THI0NE WITH AMINO ACID AND ITS DERIVATIVE: PEPTIDE BOND FORMATION, CHEMOSELECTIVE ACYLATION, AND BRIDGING REACTION
  作者：Yoshimitsu Nagao、Tadayo Miyasaka、Kaoru Seno、Masahiro Yagi、Eiichi Fujita

  DOI：10.1246/cl.1981.463

  日期：1981.4.5

  As a new extention of the monitored aminolysis of 3-acyl-l,3-thiazolidine-2-thione, its applications to peptide bond formation, chemoselective acylation of amino acid, and bridging reaction onthe enzyme model are reported.

  作为3-酰基-1,3-噻唑烷-2-硫酮氨解监测的新延伸，报道了其在肽键形成、氨基酸化学选择性酰化和酶模型桥接反应中的应用。

表征谱图