L-谷氨酸-5-苄酯-1-叔丁酯盐酸盐 | 105590-97-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 天然氨基酸及其衍生物
• 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: L-谷氨酸-5-苄酯-1-叔丁酯盐酸盐
• 中文别名: L-谷氨酸-Γ-苄酯-Α-叔丁酯盐酸盐；无中文名
• 英文名称: H-Glu(OBzl)-OtBu hydrochloride
• 英文别名: (S)-5-benzyl 1-tert-butyl 2-amino-pentanedioate hydrochloride；L-Glu(OBn)-O^tBu；H-L-Glu(OBn)-O^tBu*HCl；(S)-5-Benzyl 1-tert-butyl 2-aminopentanedioate hydrochloride；5-O-benzyl 1-O-tert-butyl (2S)-2-aminopentanedioate;hydrochloride
• CAS: 105590-97-4
• 化学式: C₁₆H₂₃NO₄*ClH
• mdl: MFCD00038897
• 分子量: 329.824
• InChiKey: TWBZXIOAVCJDKR-ZOWNYOTGSA-N

物化性质

• 熔点：
  104-107°C
• 溶解度：
  可溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.6
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S36/37
• 危险类别码：
  R43
• 海关编码：
  2922499990
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,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: H-Glu(obzl)-otbu HCl
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: H-Glu(obzl)-otbu HCl
CAS number: 105590-97-4

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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.
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: C16H23NO4.ClH
Molecular weight: 329.8

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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, hydrogen chloride.

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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

(S)-5-苄基1-叔丁基2-氨基戊二酸盐酸盐是一种谷氨酸衍生物[1]。

反应信息

• 作为反应物：
  描述：

  L-谷氨酸-5-苄酯-1-叔丁酯盐酸盐 在 palladium on activated charcoal 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 184.75h， 生成 L-谷氨酸,N-[N-[N-[N-[1-(4-氯苯甲酰)-L-脯氨酰]-L-缬氨酰]-2-甲基丙氨酰]-2-甲基丙氨酰]-,1-(1,1-二甲基乙基)5-甲基酯
  参考文献：
  名称：

  Shaw, I. M.; Taylor, A., Canadian Journal of Chemistry, 1986, vol. 64, p. 164 - 173

  摘要：

  DOI：
• 作为产物：
  描述：

  醋酸叔丁酯 、 L-谷氨酸 γ-苄酯 在 高氯酸 、 sodium carbonate 、 盐酸 作用下， 以 乙醚 、 水 为溶剂， 以80%的产率得到L-谷氨酸-5-苄酯-1-叔丁酯盐酸盐
  参考文献：
  名称：

  一种谷氨酸-5-苄酯-1-叔丁酯盐酸盐的制备方法

  摘要：

  一种谷氨酸-5-苄酯-1-叔丁酯盐酸盐的制备方法，主要解决现有合成方法存在操作难度大的技术问题。本发明的技术方案：一种谷氨酸-5-苄酯-1-叔丁酯盐酸盐的制备方法，包括以下步骤：由谷氨酸为起始原料，同苯甲醇酯化并纯化得谷氨酸-5-苄酯，然后谷氨酸-5-苄酯在催化剂催化下同醋酸叔丁酯转酯反应得谷氨酸-5-苄酯-1-叔丁酯，最后用乙醚盐酸气调酸性制得谷氨酸-5-苄酯-1-叔丁酯盐酸盐。产品用于多肽合成领域。

  公开号：

  CN105541649A

文献信息

• [EN] PSMA-TARGETING AMANITIN CONJUGATES<br/>[FR] CONJUGUÉS D'AMANITINE CIBLANT LE PSMA
  申请人：HEIDELBERG PHARMA RES GMBH

  公开号：WO2019057964A1

  公开（公告）日：2019-03-28

  The invention relates to a PSMA-targeting conjugate comprising (a) an amatoxin; (b) a small molecule PSMA-targeting moiety; and (c) optionally a linker linking said amatoxin and said small molecule PSMA-targeting moiety. The invention furthermore relates to a pharmaceutical composition comprising such conjugate.

  这项发明涉及一种PSMA靶向共轭物，包括(a)阿马毒素；(b)小分子PSMA靶向基团；以及(c)可选地连接所述阿马毒素和所述小分子PSMA靶向基团的连接剂。此外，该发明还涉及包含这种共轭物的药物组合物。
• Imaging of prostate cancer: optimizing affinity to prostate specific membrane antigen by spacer modifications in a tumor spheroid model
  作者：Mena Asha Krishnan、Amit Pandit、Rajesh Sharma、Venkatesh Chelvam

  DOI：10.1080/07391102.2021.1936642

  日期：2022.11.29

  highly over-expressed on PCa cells, is an excellent target for selective imaging of PCa. In recent years, various scaffolds have been explored as potential carriers to target diagnostic and therapeutic agents to PSMA+ tumour cells. Numerous fluorescent or radioisotope probes linked via a peptide linker have been developed that selectively binds to PCa cells. However, there are very few reports that examine

  摘要 前列腺癌 (PCa) 的早期诊断对于患者的分期、治疗和管理至关重要。前列腺特异性膜抗原 (PSMA) 在 PCa 细胞上高度过表达，是 PCa 选择性成像的极好靶标。近年来，人们探索了各种支架作为将诊断和治疗剂靶向 PSMA +肿瘤细胞的潜在载体。已经开发出许多通过肽接头连接的荧光或放射性同位素探针，可选择性地结合 PCa 细胞。然而，很少有报道检查成像探针的肽接头中的化学修饰对其与 PSMA 蛋白的亲和力的影响。本报告系统地研究了肽接头中疏水性芳香部分对 PSMA 亲和力和体外的影响表现。为此，设计、合成了一系列具有不同芳香间隔基的荧光生物偶联物12 - 17 ，并首先在计算机上分析了它们在 PSMA 口袋内的相互作用。然后在 PSMA +细胞系和体外3D 肿瘤模型中对12 – 17进行细胞摄取研究。12-17的结合亲和力值被发现在36到 157.9 nM 的范围内，与17相比，在间隔子中具有三个芳族基团的
• [EN] DUPA-INDENOISOQUINOLINE CONJUGATES<br/>[FR] CONJUGUÉS DUPA-INDÉNOISOQUINOLINE
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2015069766A1

  公开（公告）日：2015-05-14

  A targeting ligand-cytotoxic drug conjugate, for example, a DUPA-Indenoisoquinoline conjugate, is useful for treating cancers, e.g., prostate cancer.

  一种靶向配体-细胞毒性药物结合物，例如DUPA-Indenoisoquinoline结合物，可用于治疗癌症，例如前列腺癌。
• Novel solid-phase strategy for the synthesis of ligand-targeted fluorescent-labelled chelating peptide conjugates as a theranostic tool for cancer
  作者：Sagnik Sengupta、Mena Asha Krishnan、Premansh Dudhe、Ramesh B Reddy、Bishnubasu Giri、Sudeshna Chattopadhyay、Venkatesh Chelvam

  DOI：10.3762/bjoc.14.244

  日期：——

  demonstrated a novel continuous process for assembling targeting ligands, peptidic spacers, fluorescent tags and a chelating core for the attachment of cytotoxic molecules, radiotracers, nanomaterials in a standard Fmoc solid-phase peptide synthesis in high yield and purity. The differentially protected Fmoc-Lys-(Tfa)-OH plays a vital role in attaching fluorescent tags while growing the peptide chain in

  在本文中，我们成功设计并演示了一种新颖的连续过程，该过程可用于以高收率在标准Fmoc固相肽合成中组装靶向配体，肽间隔子，荧光标签和螯合核心，以附着细胞毒性分子，放射性示踪剂，纳米材料和纯度。差异保护的Fmoc-Lys-（Tfa）-OH在附着荧光标签时起着至关重要的作用，同时以不间断的方式生长肽链。当采用对酸敏感的侧链氨基保护基团（例如Trt（氯三苯甲基），Mtt（4-甲基三苯甲基），Mmt（4-甲氧基三苯甲基））敏感时，该方法适用于对轻度和强酸性条件敏感的固相树脂合成配体靶向的荧光标记的生物缀合物。使用这种方法，DUPA罗丹明B共轭物（DUPA = 2- [3-（1,3-二羧丙基）脲基]戊二酸），靶向在前列腺癌，乳腺癌，膀胱癌和脑癌中表达的前列腺特异性膜抗原（PSMA），以及聚ero酸酯罗丹明B，靶向叶酸已经合成了诸如卵巢癌，肺癌，子宫内膜之类的受体阳性癌症以及炎性疾病。使用LNCaP（PSMA
• [EN] HYDROXY FORMAMIDE DERIVATIVES AND THEIR USE<br/>[FR] DÉRIVÉS D'HYDROXY FORMAMIDE ET LEUR UTILISATION
  申请人：GLAXOSMITHKLINE IP NO 2 LTD

  公开号：WO2015104684A1

  公开（公告）日：2015-07-16

  Disclosed are compounds having the formula (I): wherein R1, R2 and R3 are as defined herein, and methods of making and using the same, including use as inhibitors of BMP1, TLL1 and/or TLL2 and in treatment of diseases associated with BMP1, TLL1 and/or TLL2 activity.

  揭示了具有以下化学式（I）的化合物：其中R1、R2和R3如本文所定义，并且制备和使用这些化合物的方法，包括用作BMP1、TLL1和/或TLL2的抑制剂以及用于治疗与BMP1、TLL1和/或TLL2活性相关的疾病。