芴甲氧羰基-L-谷氨酸 1-叔丁酯 | 84793-07-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 谷氨酸类衍生物
• 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: 芴甲氧羰基-L-谷氨酸 1-叔丁酯
• 中文别名: 芴甲氧羰基-L-谷氨酸1叔丁脂；N-芴甲氧羰基-L-谷氨酸1-叔丁酯；芴甲氧羰基-L-谷氨酸1-叔丁酯；Fmoc-L-谷氨酸1-叔丁酯；FMOC-L-谷氨酸1-叔丁酯；Fmoc-L-谷氨酸-1-叔丁酯；Fmoc-L-谷氨酸 1-叔丁酯；Fmoc-Glu-OtBu
• 英文名称: Fmoc-Glu-OtBu
• 英文别名: (S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid；Fmoc-L-glutamic acid 5-tert-butyl ester；N-Fmoc-L-glutamic acid tert-butyl ester；Fmoc-L-Glu-O^tBu；(4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid
• CAS: 84793-07-7
• 化学式: C₂₄H₂₇NO₆
• mdl: MFCD00065648
• 分子量: 425.481
• InChiKey: GOPWHXPXSPIIQZ-FQEVSTJZSA-N

物化性质

• 熔点：
  78-80 °C
• 沸点：
  638.1±55.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  29224290
• 危险品标志：
  C
• WGK Germany：
  3
• 危险类别：
  8
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R34
• 包装等级：
  III
• 危险品运输编号：
  UN 3261 8/PG 2
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  | 冷藏 |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-Glu-OtBu
Synonyms: Fmoc-L-glutamic acid, alfa-tert-butyl ester

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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: Fmoc-Glu-OtBu
CAS number: 84793-07-7

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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.

---

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: C24H27NO6
Molecular weight: 425.5

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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

用途

芴甲氧羰基-L-谷氨酸 1-叔丁酯是谷氨酸-1-叔丁酯的一种衍生物，在多肽合成中常用作基础原料。它被广泛用于合成利拉鲁肽、胸腺法新肽等多种药物肽。

制备 (1) 谷氨酸-1-叔丁酯的制备

在2000毫升三口瓶中加入581克醋酸叔丁酯和147克谷氨酸，搅拌后滴加100毫升高氯酸，在20℃下反应48小时。随后降温至0℃，加入600毫升水，用Na2CO3调节pH值至8～9，进行分液，并用水洗三次（每次使用100毫升1%的Na2CO3溶液）。合并后的水相用200毫升石油醚萃取三次。

(2) 粗产品芴甲氧羰基-L-谷氨酸 1-叔丁酯的制备

将步骤(1)得到的水相转入2升三口瓶中，再加入187.5克CuSO4·5H2O，并搅拌。用碳酸钠调节pH至8～9后，加入四氢呋喃100毫升和Fmoc-OSu 33.7克（维持pH为8～9），反应8小时制得粗产品芴甲氧羰基谷氨酸-1-叔丁酯。随后用HCl酸化并用乙酸乙酯萃取，减压浓缩结晶后过滤、烘干，最终得到36克芴甲氧羰基-L-谷氨酸 1-叔丁酯。

通过HPLC分析，该产品纯度为99.1%，旋光度为-9.4（c＝1, in HAc），熔点为109.5～110.6℃，异构体含量为0.03%。

反应信息

• 作为反应物：
  描述：

  芴甲氧羰基-L-谷氨酸 1-叔丁酯 在 三异丙基硅烷 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 Fmoc-Gln[Gal(OAc)4]-OH
  参考文献：
  名称：

  A convenient preparation of several N-linked glycoamino acid building blocks for efficient solid-phase synthesis of glycopeptides

  摘要：

  本研究提出了一条便捷且产率高的制备多个Boc和Fmoc保护的N-连接糖肽单体的方法。这些构建单元可用于糖肽或糖肽模拟物的固相合成，通过制备N-连接的十二糖肽Ac–(GlyProAsn[Gal])4–NH2为例，展示了其作为潜在胶原蛋白模拟物的应用。

  DOI：

  10.1039/b201296k
• 作为产物：
  描述：

  芴甲氧羰基-L-谷氨酸-Γ-苄脂 在 palladium on activated charcoal 吡啶 、 氢气 、 三氯氧磷 作用下， 生成 芴甲氧羰基-L-谷氨酸 1-叔丁酯
  参考文献：
  名称：

  A convenient preparation of several N-linked glycoamino acid building blocks for efficient solid-phase synthesis of glycopeptides

  摘要：

  本研究提出了一条便捷且产率高的制备多个Boc和Fmoc保护的N-连接糖肽单体的方法。这些构建单元可用于糖肽或糖肽模拟物的固相合成，通过制备N-连接的十二糖肽Ac–(GlyProAsn[Gal])4–NH2为例，展示了其作为潜在胶原蛋白模拟物的应用。

  DOI：

  10.1039/b201296k

文献信息

• [EN] SUPRAMOLECULAR GEL SUPPORTED ON OPEN-CELL POLYMER FOAM<br/>[FR] GEL SUPRAMOLÉCULAIRE SUPPORTÉ SUR MOUSSE POLYMÈRE À CELLULES OUVERTES
  申请人：UNIV STRASBOURG

  公开号：WO2021048199A1

  公开（公告）日：2021-03-18

  The present invention relates to a polymer foam, said polymer foam comprising pores forming an open-cell polymer foam, said polymer foam comprising a supramolecular gel inside pores, and said polymer foam comprising at least one enzyme. The present invention relates to a supramolecular gel; its preparation and its applications, notably in chemical synthesis and kinetic resolution, in particular of organic compounds. The present invention also relates to flow chemistry.

  本发明涉及一种聚合物泡沫，所述聚合物泡沫包括形成开孔聚合物泡沫的孔隙，所述聚合物泡沫包括孔隙内的超分子凝胶，以及所述聚合物泡沫包括至少一种酶。本发明涉及一种超分子凝胶；其制备及其应用，特别是在化学合成和动力学分辨中的应用，特别是有机化合物的动力学分辨。本发明还涉及流动化学。
• [EN] CONJUGATES FOR TREATING DISEASES<br/>[FR] CONJUGUÉS POUR LE TRAITEMENT DE MALADIES
  申请人：ENDOCYTE INC

  公开号：WO2016148674A1

  公开（公告）日：2016-09-22

  The present disclosure relates to pyrrolobenzodiazepine (PBD) prodrugs and conjugates thereof. The present disclosure also relates to pharmaceutical compositions of the conjugates described herein, methods of making and methods of using the same.

  本公开涉及吡咯苯并二氮杂环（PBD）前药及其结合物。本公开还涉及所述结合物的药物组合物，制备方法和使用方法。
• SILICON BASED DRUG CONJUGATES AND METHODS OF USING SAME
  申请人：BlinkBio, Inc.

  公开号：US20170202970A1

  公开（公告）日：2017-07-20

  Described herein are silicon based conjugates capable of delivering one or more payload moieties to a target cell or tissue. Contemplated conjugates may include a silicon-heteroatom core, one or more optional catalytic moieties, a targeting moiety that permits accumulation of the conjugate within a target cell or tissue, one or more payload moieties (e.g., a therapeutic agent or imaging agent), and two or more non-interfering moieties covalently bound to the silicon-heteroatom core.

  本文描述了基于硅的共轭物，能够将一个或多个有效载荷基团传递到靶细胞或组织。考虑到的共轭物可能包括一个硅-杂原子核心，一个或多个可选的催化基团，一个定位基团，允许共轭物在靶细胞或组织内积累，一个或多个有效载荷基团（例如，治疗剂或成像剂），以及与硅-杂原子核心共价结合的两个或更多个不干扰基团。
• PSMA激活式抗肿瘤前药CPT-Y及其制备方法和应用
  申请人：薪火炙药（北京）科技有限公司

  公开号：CN112294972A

  公开（公告）日：2021-02-02

  本发明提供了一类具有结构通式1或结构通式2的化合物及其制备方法和在制备抗肿瘤药物中的应用。本发明中将前列膜抗原(PSMA)特异性靶向多肽与喜树碱，通过化学键进行连接，构建两亲性的PSMA激活前药CPT‑Y(CPT‑Wn和CPT‑Hn)。两亲性化合物的构建可提高喜树碱的水溶性、稳定性和半衰期，从而提高生物利用度。同时本发明物CPT‑Y通过PSMA介导的主动靶向作用可以将喜树碱定向转运至肿瘤部位释放，从而降低其对健康细胞和正常组织的杀伤力，改善耐药性的同时，提升抗肿瘤效应。
• Novel Analogs of Camptothecin
  申请人：FL Therapeutics, LLC

  公开号：US20140135356A1

  公开（公告）日：2014-05-15

  The present invention provides novel conjugates of camptothecin and camptothecin analogs with a linker and an HSA-binding moiety. The novel conjugates are prodrug forms of the camptothecin or camptothecin analogs and can be used to treat mammalian cell proliferative diseases, such as cancer.

  本发明提供了新型累积毒素和累积毒素类似物与连接剂和HSA结合基团的结合物。这些新型结合物是累积毒素或累积毒素类似物的前药形式，可用于治疗哺乳动物细胞增殖性疾病，如癌症。