N-[苄氧羰基]-L-谷氨酸 5-叔丁酯 1-甲酯 | 56877-41-9

• 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: N-[苄氧羰基]-L-谷氨酸 5-叔丁酯 1-甲酯
• 中文别名: N-[苄氧羰基]-L-谷氨酸5-叔丁酯1-甲酯；苄氧羰基-5-苄酯-D-谷氨酸-甲酯
• 英文名称: methyl 2(S)-2-benzyloxycarbonylamino-4-tert-butoxycarbonylbutanoate
• 英文别名: Z-L-Glu(O-tBu)-OMe；N-Z-L-Glutaminsaeure-α-methylester-γ-tert.-butylester；Benzyloxycarbonyl-L-glutaminsaeure-1-methylester-5-tert.-butylester；Z-Glu(otbu)-ome；5-O-tert-butyl 1-O-methyl (2S)-2-(phenylmethoxycarbonylamino)pentanedioate
• CAS: 56877-41-9
• 化学式: C₁₈H₂₅NO₆
• 分子量: 351.4
• InChiKey: BRMSLIYSWUEHJT-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 储存条件：
  室温、密封、干燥保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-Glu(OtBu)-OMe
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: Z-Glu(OtBu)-OMe
CAS number: 56877-41-9

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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: C18H25NO6
Molecular weight: 351.4

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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

反应信息

• 作为反应物：
  描述：

  N-[苄氧羰基]-L-谷氨酸 5-叔丁酯 1-甲酯 在 sodium tetrahydroborate 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以91%的产率得到S-4-benzyloxycarbonylamino-5-hydroxy-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  环形肽dolastatin 3（一种强大的细胞生长抑制剂）的拟议结构应该修改！

  摘要：

  通过使用叠氮磷酸二苯酯（DPPA）和磷酸氰基二乙酯（DEPC）合成了功能强大的抑制细胞生长的dolastatin 3及其非对映异构体及其异构体的环状肽。它们的理化和生物学特性表明所提出的结构是站不住脚的。

  DOI：

  10.1016/s0040-4039(01)81589-6
• 作为产物：
  描述：

  N-苄氧羰基-L-谷氨酸酐 在 甲醇 、 硫酸 作用下， 生成 N-[苄氧羰基]-L-谷氨酸 5-叔丁酯 1-甲酯
  参考文献：
  名称：

  Klieger,E.; Gibian,H., Justus Liebigs Annalen der Chemie, 1962, vol. 655, p. 195 - 210

  摘要：

  DOI：

文献信息

• Unusual Orthogonality in the Cleavage Process of Closely Related Chelating Protecting Groups for Carboxylic Acids by Using Different Metal Ions
  作者：Stephan Mundinger、Uwe Jakob、Willi Bannwarth

  DOI：10.1002/chem.201302708

  日期：2014.1.27

  conditions, these protecting groups are also stable under acidic and basic conditions, allowing them to be used in combination with the ester protection of carboxylic acids. The cleavage of these protecting groups is activated by the chelation of metal ions, involving an unusual coordination of the amide nitrogen. Despite their similarity, cleavage of these protecting groups is possible in both a stepwise

  已经开发了基于螯合胺的三个结构上相关的羧酸中继保护基。这些保护基可以很容易地通过在2-（1 H-苯并三唑-1-基）-1,1,3,3-四甲基溴化四氟硼酸盐（TBTU）。这些保护基除了对整个反应条件稳定外，在酸性和碱性条件下也稳定，因此可以与羧酸的酯保护剂结合使用。这些保护基的裂解被金属离子的螯合激活，这涉及酰胺氮的异常配位。尽管它们相似，但是通过施加不同的金属盐，可以逐步和正交方式裂解这些保护基。
• Cleavage of benzyloxycarbonyl-5-oxazolidinones to α-benzyloxycarbonylamino-α-alkyl esters by alcohols and sodium hydrogen carbonate
  作者：Pietro Allevi、Giuliana Cighetti、Mario Anastasia

  DOI：10.1016/s0040-4039(01)00971-6

  日期：2001.7

  The reaction of benzyloxycarbonyl-5-oxazolidinones with alcohols and sodium hydrogen carbonate to afford the corresponding benzyloxycarbonyl esters is described.

  描述了苄氧羰基-5-恶唑烷酮与醇和碳酸氢钠的反应，得到相应的苄氧羰基酯。
• TBAT-Mediated Nitrone Formation of ω-Mesyloxy-<i>O-tert</i>-butyldiphenylsilyl-oximes: Facile Synthesis of Cyclic Nitrones from Hemiacetals
  作者：Osamu Tamura、Hiroyuki Ishibashi、Atsushi Toyao

  DOI：10.1055/s-2002-32988

  日期：——

  Chiral and cyclic nitrones were synthesized by TBAT-mediated desilylative cyclization of ω-mesyloxy-O-tert-butyl-diphenylsilyloximes, readily prepared from sugar derivatives by a consecutive treatment with O-tert-butyldiphenylsilylhydroxylamine and with mesyl chloride. The method was applied to sequential nitrone formation and intramolecular cycloaddition.

  手性和环状硝酮是通过 TBAT 介导的 ω-甲磺酰氧基-O-叔丁基-二苯基甲硅烷基肟的脱甲硅烷基化环化合成的，通过用 O-叔丁基二苯基甲硅烷基羟胺和甲磺酰氯连续处理从糖衍生物中很容易制备。该方法应用于连续硝酮形成和分子内环加成。
• Cell-Impermeable Inhibitors Confirm That Intracellular Human Transglutaminase 2 Is Responsible for the Transglutaminase-Associated Cancer Phenotype
  作者：Eric W. J. Gates、Nicholas D. Calvert、Nicholas J. Cundy、Federica Brugnoli、Pauline Navals、Alexia Kirby、Nicoletta Bianchi、Gautam Adhikary、Adam J. Shuhendler、Richard L. Eckert、Jeffrey W. Keillor

  DOI：10.3390/ijms241612546

  日期：——

  Transglutaminase 2 (TG2) is a multifunctional enzyme primarily responsible for crosslinking proteins. Ubiquitously expressed in humans, TG2 can act either as a transamidase by crosslinking two substrates through formation of an Nε(ɣ-glutaminyl)lysine bond or as an intracellular G-protein. These discrete roles are tightly regulated by both allosteric and environmental stimuli and are associated with dramatic changes in the conformation of the enzyme. The pleiotropic nature of TG2 and multi-faceted activities have resulted in TG2 being implicated in numerous disease pathologies including celiac disease, fibrosis, and cancer. Targeted TG2 therapies have not been selective for subcellular localization, such that currently no tools exist to selectively target extracellular over intracellular TG2. Herein, we have designed novel TG2-selective inhibitors that are not only highly potent and irreversible, but also cell impermeable, targeting only extracellular TG2. We have also further derivatized the scaffold to develop probes that are intrinsically fluorescent or bear an alkyne handle, which target both intra- and extracellular TG2, in order to facilitate cellular labelling and pull-down assays. The fluorescent probes were internalized and imaged in cellulo, and provide the first implicit experimental evidence that by comparison with their cell-impermeable analogues, it is specifically intracellular TG2, and presumably its G-protein activity, that contributes to transglutaminase-associated cancer progression.

  转谷氨酰胺酶 2（TG2）是一种多功能酶，主要负责交联蛋白质。TG2 在人体内无独有偶地表达，它既可以通过形成 Nε(ɣ-谷氨酰胺酰)赖氨酸键交联两个底物而充当转氨基酶，也可以充当细胞内的 G 蛋白。这些不同的作用受到异构和环境刺激的严格调控，并与酶构象的剧烈变化有关。TG2 的多效性和多方面活性导致 TG2 与乳糜泻、纤维化和癌症等多种疾病病理有关。靶向 TG2 的疗法对亚细胞定位没有选择性，因此目前还没有工具可以选择性地靶向细胞外而不是细胞内的 TG2。在此，我们设计出了新型 TG2 选择性抑制剂，不仅药效高、不可逆，而且不渗透细胞，只针对细胞外 TG2。我们还对该支架进行了进一步衍生，开发出了同时针对细胞内和细胞外 TG2 的本征荧光探针或带有炔柄的探针，以方便细胞标记和牵引检测。这些荧光探针在细胞内被内化并成像，首次提供了隐含的实验证据，证明与细胞不渗透的类似物相比，细胞内的 TG2（可能是其 G 蛋白活性）才是导致转谷氨酰胺酶相关癌症进展的原因。
• Compound bearing beta-galactoside-introduced self-immolative linker
  申请人：IntoCell Inc.

  公开号：US11065343B2

  公开（公告）日：2021-07-20

  The present invention relates to a compound bearing a self-immolative linker having β-galactoside-introduced thereto. In a compound bearing a β-galactoside-introduced self-immolative linker according to the present invention, particularly, the self-immolative linker may form a glycosidic bond with a protein (e.g., an oligopeptide, polypeptide, an antibody, etc.) or ligand which has specific affinity for a desired target or with an active agent (e.g., a drug, a toxin, a ligand, a detection probe, etc.), which has a specific function or activity so as to allow the selective release of the active agent within a target cell.

  本发明涉及一种含有自巯基连接体的化合物，该连接体中引入了β-半乳糖苷。根据本发明，在含有引入了β-半乳糖苷的自巯基连接体的化合物中，特别是自巯基连接体可与蛋白质（例如、寡肽、多肽、抗体等）或配体形成糖苷键，这些蛋白质或配体对所需靶标或活性剂（如药物、毒素、配体、检测探针等）具有特定的亲和力，具有特定的功能或活性，从而使活性剂在靶细胞内选择性释放。