4-((S)-2-叔-丁氧基羰基氨基-2-甲酯基 | 17791-51-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 组氨酸类衍生物
• 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: 4-((S)-2-叔-丁氧基羰基氨基-2-甲酯基
• 中文别名: N(Α),N-(IM)-二-BOC-L-组氨酸甲酯；N(α),N-(im)-二-Boc-L-组氨酸甲酯
• 英文名称: 4-(2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-1H-imidazole-1-carboxylic acid tert-butyl ester
• 英文别名: N-α-(tert-butoxycarbonyl)-1-tert-butoxycarbonyl histidine methyl ester；Boc-His(N^τ-Boc)-OMe；N(α),N(τ)-bis-(t-butoxycarbonyl)-L-histidine methyl ester；Boc-His(Boc)-Ome；tert-butyl (S)-4-(2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)-1H-imidazole-1-carboxylate；(S)-tert-butyl 4-(2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)-1H-imidazole-1-carboxylate；N(alpha), N-(im)-Di-Boc-L-histidine methyl ester；tert-butyl 4-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]imidazole-1-carboxylate
• CAS: 17791-51-4
• 化学式: C₁₇H₂₇N₃O₆
• 分子量: 369.418
• InChiKey: ZYCZFTGHOVFXLZ-LBPRGKRZSA-N

物化性质

• 熔点：
  113-116 °C (lit.)
• 稳定性/保质期：
  按规定使用不会分解，避免氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 储存条件：
  2-8°C冷藏，密闭保存，并置于干燥处。

SDS

---

Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: N(α), N-(im)-Di-Boc-L-histidine methyl ester
Product name
CAS-No. : 17791-51-4
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : [Methyl(S)-3[1-(1,1-dimethylethoxycarbonyl)-1-H-imidazol-4-yl]-2-[(1,1-
dimethylethoxycarbonyl)amino]propionate]
Formula : C17H27N3O6
Molecular Weight : 369,41 g/mol

---

Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

---

Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

---

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

---

Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
Specific end uses
no data available

---

Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 113 - 116 °C - lit.
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

---

Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

---

Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

---

Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

---

Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

---

Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

---

Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

---

Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

N(α),N'-二乙酰氧基羰基-L-异丙基组氨酯甲酯是一种组氨酸衍生物[1]。

反应信息

• 作为反应物：
  描述：

  4-((S)-2-叔-丁氧基羰基氨基-2-甲酯基 在 甲醇 、 potassium carbonate 作用下， 反应 3.0h， 生成 N-叔丁基氧羰基-L-组氨酸甲酯
  参考文献：
  名称：

  猪布鲁氏组织化醇脱氢酶：一系列从组氨酸衍生的取代苄基酮的合成和抑制研究。

  摘要：

  布鲁氏菌属。是布鲁氏菌病（马耳他热）的病原体，布鲁氏菌病是世界上最广泛的人畜共患病。该病原体能够在人类中建立持续的感染，即使使用抗生素治疗也难以根除。此外，布鲁切拉被认为是一种潜在的生物恐怖主义行为。组蛋白醇脱氢酶（HDH，EC 1.1.1.23）已被证明对于这种病原体的宏吞噬复制是必不可少的。因此，它构成了抗Brucella药剂开发的原始且新颖的靶标。在这项工作中，我们从猪布鲁氏菌中克隆并过表达了HDH编码基因，纯化了该蛋白质并证明了其生物学活性。然后，我们研究了一系列从组氨酸衍生的取代苄基酮的抑制作用。

  DOI：

  10.1016/j.bmc.2007.04.027
• 作为产物：
  描述：

  L-组氨酸 在 氯化亚砜 、 三乙胺 作用下， 反应 40.0h， 生成 4-((S)-2-叔-丁氧基羰基氨基-2-甲酯基
  参考文献：
  名称：

  N（π）-2-萘甲氧基甲基保护的组氨酸：肽合成的可扩展，无消旋结构单元

  摘要：

  组氨酸（His）在肽合成过程中相对容易消旋。抑制该消旋作用的一种策略是用合适的保护基保护His中咪唑部分的氮原子。在已经测试的众多保护基团中，π-氮原子上的对甲氧基苄氧基甲基（PMBOM）​​基团有效地抑制了消旋作用。然而，迄今为止，由于需要新鲜制备的不稳定试剂，阻碍了N（π）-PMBOM-保护的衍生物的大规模合成。在此我们报告N的合成（π）-2-萘甲氧基甲基（NAPOM）-保护的His衍生物，其可以克量级制备并且不遭受上述不稳定性问题。此外，这些NAPOM保护的His衍生物可抑制基于Boc和Fmoc的肽合成中的外消旋作用。

  DOI：

  10.1021/acs.oprd.9b00538

文献信息

• Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes
  作者：Steven M. Wales、Daniel J. Rivinoja、Michael G. Gardiner、Melissa J. Bird、Adam G. Meyer、John H. Ryan、Christopher J. T. Hyland

  DOI：10.1021/acs.orglett.9b01580

  日期：2019.6.21

  N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving

  带有3,5-二硝基苯基侧基的氨基苯甲醛与N-取代的α-氨基酸发生热反应，形成前所未有的苯并氮杂稠合的异二氢吲哚。反应通过脱芳香化/再芳香化顺序进行，该顺序涉及原位形成的甲亚胺基立德和二硝基芳烃之间的分子内（3 + 2）-环加成。基于环状，α-单-和α，α-二取代的氨基酸，可以耐受各种甘氨酸衍生物以及支链的底物，在许多情况下可得到单一的非对映异构体。该方法是可扩展的，并提供具有硝基基团的产品以备进一步处理。
• N-morpholino derivatives and their use as anti-hypertensive agents
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05055466A1

  公开（公告）日：1991-10-08

  Compounds of the formula ##STR1## are disclosed. These compounds are inhibitors of renin and therefore useful as cardiovascular agents.

  公开了式##STR1##的化合物。这些化合物是肾素抑制剂，因此可用作心血管药物。
• Peptide mimetic ligands of polo-like kinase 1 polo box domain and methods of use
  申请人：Burke, Jr. Terrence R.

  公开号：US10266565B2

  公开（公告）日：2019-04-23

  Novel compounds are provided that bind to polo-like kinases through the polo-box domain. In certain embodiments, the novel compounds are PEGylated peptides. The PEGylated peptides in accordance with the invention demonstrate high PBD-binding affinity. In certain embodiments, the PEGylated peptides have also achieved activities in whole cell systems. The invention also provides compounds that bind polo-like kinases through the polo-box domain and possess reduced anionic charge. Further provided are methods of design and/or synthesis of the PEGylated peptides and methods of use thereof. The invention provides methods of use of the compounds and methods of synthesis of the compounds.

  提供了一种新型化合物，通过波洛盒结构结合波洛样激酶。在某些实施例中，这些新型化合物是PEG化肽。根据本发明，这些PEG化肽表现出高PBD结合亲和力。在某些实施例中，这些PEG化肽在整个细胞系统中也表现出活性。本发明还提供了一种通过波洛盒结构结合波洛样激酶且具有降低阴离子电荷的化合物。此外，还提供了PEG化肽的设计和/或合成方法以及使用这些方法。本发明提供了这些化合物的使用方法和合成方法。
• Synthesis of Imidazole and Histidine-Derived Cross-Linkers as Analogues of GOLD and Desmosine
  作者：Ursula Bilitewski、Sabine Laschat、Nicole Schädel、Esra Icik、Maike Martini、Luca Altevogt、Isabell Ramming、Andreas Greulich、Angelika Baro

  DOI：10.1055/s-0040-1706144

  日期：2021.7

  Amino acid derivatives with a central cationic heterocyclic core (e.g., imidazolium) are biologically relevant cross-linkers of proteins and advanced glycation end (AGE) products. Here, imidazolium-containing cross-linkers were synthesized from imidazole or histidine by N-alkylation employing aspartate- and glutamate-derived mesylates as key step. Biological investigations were carried out to probe

  具有中央阳离子杂环核心（例如，咪唑鎓）的氨基酸衍生物是蛋白质和高级糖基化末端（AGE）产物的生物学相关交联剂。在此，以天冬氨酸和谷氨酸衍生的甲磺酸酯为关键步骤，通过N-烷基化由咪唑或组氨酸合成了含咪唑鎓的交联剂。进行了生物学研究以探测这些化合物的生物相容性。
• Synthesis of 2-isoxazoline and α-hydroxy ketomethylene dipeptide isosteres
  作者：Yong Jun Chung、Eun Jung Ryu、Gyochang Keum、Kim Byeang Hyean

  DOI：10.1016/0968-0896(95)00174-3

  日期：1996.2

  We have developed a simple and stereoselective method for synthesizing novel dipeptide isosteres using nitrile oxide cycloaddition as a key reaction. Employing this method, we have prepared efficiently various peptidomimetics containing 2-isoxazolines and alpha-hydroxy ketomethylene dipeptide isosteres.

  我们已经开发了一种简单且立体选择性的方法，用于使用一氧化氮环加成作为关键反应来合成新型二肽等位基因。利用这种方法，我们有效地制备了各种含有2-异恶唑啉和α-羟基酮亚甲基二肽等排体的拟肽。