(S)-2-(2-((叔丁氧基羰基)氨基)-4-甲基戊酰胺)乙酸 | 32991-17-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 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: (S)-2-(2-((叔丁氧基羰基)氨基)-4-甲基戊酰胺)乙酸
• 中文别名: 叔丁氧羰基-L-亮氨酰-L-甘氨酸；N-{[(2-甲基-2-丙基)氧基]羰基}-L-亮氨酰甘氨酸
• 英文名称: Boc-Leu-Gly-OH
• 英文别名: Boc-Leu-Gly；(S)-2-(2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)acetic acid；2-[[(2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]acetic acid
• CAS: 32991-17-6
• 化学式: C₁₃H₂₄N₂O₅
• mdl: MFCD00076954
• 分子量: 288.344
• InChiKey: NRXDUMDULDHIEA-VIFPVBQESA-N

物化性质

• 沸点：
  499.6±30.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.769
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  | 2-8°C |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-Leu-Gly-OH
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Boc-Leu-Gly-OH
CAS number: 32991-17-6

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

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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
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C13H24N2O5
Molecular weight: 288.3

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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.

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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

(叔丁氧羰基)-L-亮氨酸甘氨酸是一种以甘氨酸（HY-Y0966）为衍生物的化合物。

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-((叔丁氧基羰基)氨基)-4-甲基戊酰胺)乙酸 在 4-二甲氨基吡啶 N-甲基吗啉 、 三聚氯氰 、 盐酸羟胺 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到Boc-Leu-Gly-NHOH
  参考文献：
  名称：

  简单的一瓶法制备异羟肟酸。

  摘要：

  [反应：见正文]描述了在非常温和的条件下将羧酸一步转化为异羟肟酸的方法。这种简单而有效的方法已被用于合成α-氨基酸和肽的对映体纯异羟肟酸酯。

  DOI：

  10.1021/ol034903j
• 作为产物：
  描述：

  (S)-methyl 2-(2-((tert-butoxycarbonyl)amino)-4-methylpentanamido)acetate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到(S)-2-(2-((叔丁氧基羰基)氨基)-4-甲基戊酰胺)乙酸
  参考文献：
  名称：

  Synthetic and Cytotoxic and Antimicrobial Activity Studies on Annomuricatin B

  摘要：

  合成和细胞毒性以及抗菌活性研究：关于Annomuricatin B

  DOI：

  10.1515/znb-2009-0215

文献信息

• Photoinduced Decarboxylative Radical Addition Reactions for Late Stage Functionalization of Peptide Substrates
  作者：Patricia Fernandez‐Rodriguez、Fabien Legros、Thomas Maier、Angelika Weber、María Méndez、Volker Derdau、Gerhard Hessler、Michael Kurz、Ana Villar‐Garea、Sven Ruf

  DOI：10.1002/ejoc.202001178

  日期：2021.2.5

  In our contribution we showcase an application of photochemistry for Late Stage Functionalization (LSF) of amino acids and small peptides in an industrial medicinal chemistry environment. The radical intermediates generated under photochemical conditions from the C‐terminal carboxylates undergo rapid 1,4‐conjugate additions to a variety of Michael acceptors. The studied methodology is applicable to

  在我们的贡献中，我们展示了在工业药物化学环境中光化学在氨基酸和小肽的后期功能化（LSF）中的应用。在光化学条件下，由C末端羧酸盐生成的自由基中间体会快速与各种Michael受体进行1,4-共轭加成。研究的方法学适用于已建立的药物和药物前体的功能化。
• Design, synthesis and preliminary evaluation of α-sulfonyl γ-(glycinyl-amino)proline peptidomimetics as matrix metalloproteinase inhibitors
  作者：Jian Zhang、Xiaoyang Li、Yuqi Jiang、Jinhong Feng、Xiaoguang Li、Yingjie Zhang、Wenfang Xu

  DOI：10.1016/j.bmc.2013.12.025

  日期：2014.6

  A series of novel α-sulfonyl γ-(glycinyl-amino)proline peptidomimetic derivatives were designed, synthesized and assayed for their activities against matrix metalloproteinase-2 (MMP-2), aminopeptidase N (APN)/CD13 and HDACs. The results indicated that all the compounds exhibited highly selective inhibition against MMP-2 as compared with APN and HDACs. The antiproliferative activities of some compounds

  设计，合成和测定了一系列新型的α-磺酰基γ-（甘氨酰氨基）脯氨酸拟肽衍生物，它们对基质金属蛋白酶-2（MMP-2），氨基肽酶N（APN）/ CD13和HDAC的活性。结果表明，与APN和HDAC相比，所有化合物均显示出对MMP-2的高度选择性抑制。还研究了某些化合物对SKOV3，HL60和A549细胞的抗增殖活性。与对照LY52相比，在酶促抑制分析和基于细胞的分析中均具有优异活性的化合物12u可用作进一步开发MMP抑制剂的先导化合物。
• Conversion of glycals into vicinal-1,2-diazides and 1,2-(or 2,1)-azidoacetates using hypervalent iodine reagents and Me₃SiN₃. Application in the synthesis of N-glycopeptides, pseudo-trisaccharides and an iminosugar
  作者：Ande Chennaiah、Srijita Bhowmick、Yashwant D. Vankar

  DOI：10.1039/c7ra08637g

  日期：——

  Glycals were found to react with a reagent system comprising of phenyliodine bis(trifluoroacetate) (PIFA) and Me3SiN3 in the presence of TMSOTf as a catalyst to form the corresponding vicinal 1,2-diazides. On the other hand, they reacted with another reagent system phenyliodine diacetate (PIDA) and Me3SiN3, also in the presence of TMSOTf as a catalyst, to lead to the corresponding vicinal 1,2-azidoacetates

  发现乙二醇在TMSOTf作为催化剂存在下与包含苯基碘双（三氟乙酸盐）（PIFA）和Me 3 SiN 3的试剂系统反应形成相应的邻位1,2-二叠氮化物。另一方面，它们也在TMSOTf作为催化剂的情况下与另一种试剂体系苯乙酸二乙酸苯酯（PIDA）和Me 3 SiN 3反应，生成相应的邻位1,2-叠氮基乙酸酯。这些叠氮基衍生物被转化为许多2-叠氮基-N-糖肽，伪三糖和哌啶三醇衍生物亚氨基糖。
• Metal- and Base-Free Room-Temperature Amination of Organoboronic Acids with <i>N</i> -Alkyl Hydroxylamines
  作者：Hong-Bao Sun、Liang Gong、Yu-Biao Tian、Jin-Gui Wu、Xia Zhang、Jie Liu、Zhengyan Fu、Dawen Niu

  DOI：10.1002/anie.201802782

  日期：2018.7.20

  N‐alkyl hydroxylamines are effective reagents for the amination of organoboronic acids in the presence of trichloroacetonitrile. This amination reaction proceeds rapidly at room temperature and in the absence of added metal or base, it tolerates a remarkable range of functional groups, and it can be used in the late‐stage assembly of two complex units.

  我们发现，现成的N烷基羟胺是在三氯乙腈存在下胺化有机硼酸的有效试剂。该胺化反应在室温下快速进行，在不添加金属或碱的情况下，它可以耐受各种官能团，可用于两个复杂单元的后期组装。
• Tumour targeting prodrugs activated by metallo matrixproteinases
  申请人：——

  公开号：US20040248765A1

  公开（公告）日：2004-12-09

  A-(B) n —X   (I) A-(B) n -Q   (II) Structural Relationship of Example ( 8 ) to its Potential Metabolites 1 Numbers in Parentheses denote examples in the specification A compound is of general formula (I) wherein (A) is a moiety comprising one of more of a heterocylcic ring, a carbocyclic ring and a fused ring system, the ring or ring system being essential for a biological activity of the compound by action at a nucleic acid or protein target (B) is a bivalent spacer molecule attached directly to the ring system n is an integer 0 or 1 and (X) is a monovalent moiety containing a amide bond that is cleavable by the action of a matrix metalloproteinase enzyme such as to produce a compound of formula (II) wherein the efficacy of the biological activity of the compound of formula (II) is increased over that of the compound of formula (I).

  化合物的结构关系示例（8）与其潜在代谢产物的关系 1. 括号中的数字表示规范中的示例 化合物具有通式（I），其中（A）是包含杂环环、碳环环和融合环系统中的一个或多个的基团，该环或环系统通过作用于核酸或蛋白靶标而对化合物的生物活性至关重要；（B）是直接连接到环系统的二价间隔分子；n是整数0或1；（X）是含有可被基质金属蛋白酶酶作用而可裂解的酰胺键的一价基团，从而产生通式（II）的化合物，其中通式（II）的化合物的生物活性效力比通式（I）的化合物增加。