N-(9-芴甲氧羰基)-D-谷氨酸 1-叔丁酯 | 109745-15-5

• 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: N-(9-芴甲氧羰基)-D-谷氨酸 1-叔丁酯
• 中文别名: N-(9-芴甲氧羰基)-D-谷氨酸1-叔丁酯；N-芴甲氧羰基-D-谷氨酸1-叔丁酯
• 英文名称: Fmoc-D-Glu-OtBu
• 英文别名: (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid；Fmoc-D-Glu(OH)-O-tBu；Fmoc-Glu-O^tBu；(4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid
• CAS: 109745-15-5
• 化学式: C₂₄H₂₇NO₆
• mdl: MFCD00077054
• 分子量: 425.481
• InChiKey: GOPWHXPXSPIIQZ-HXUWFJFHSA-N

物化性质

• 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：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储于室温下。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-D-Glu-OtBu
Synonyms: Fmoc-D-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-D-Glu-OtBu
CAS number: 109745-15-5

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
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

反应信息

• 作为反应物：
  描述：

  N-(9-芴甲氧羰基)-D-谷氨酸 1-叔丁酯 在 1-辛硫醇 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Synthesis of conformationally constrained γ-d-glutamyl-meso-diaminopimelic acid derivatives as ligands of nucleotide-binding oligomerization domain protein 1 (Nod1)

  摘要：

  Nod1, an important member of the pattern recognition receptor family, remains a virtually unexploited target. Harnessing its innate immune stimulatory properties still remains an unfulfilled goal of medicinal chemistry. Nucleotide-binding oligomerization domain protein 1 (Nod1) agonists have been shown to boost the inflammatory responses against pathogenic microbes and could thus constitute a new class of broad spectrum antimicrobial agents. To gain additional insight into the structure/activity relationships of Nod1 agonistic compounds, a series of novel, conformationally constrained gamma-D-glutamyl-meso-diaminopimelic acid (iE-DAP) analogs have been designed and synthesized. Ramos-Blue cells expressing Nod1 were used to screen and validate our compounds for their Nod1-agonist activity. Their immunomodulatory properties were subsequently determined in vitro, by evaluating their capacity to induce proinflammatory cytokine and chemokine production from human peripheral blood mononuclear cells (PBMC), by themselves and in synergy with lipopolysaccharide (LPS), a Toll-like receptor 4 (TLR4) ligand. The synthesized iE-DAP analogs were shown to possess immuno-enhancing properties as a result of their potent and specific Nod1-agonistic effect. The activity of the compound exhibiting the greatest capacity to induce pro-inflammatory cytokine release from PBMC surpassed that of lauroyl-gamma-D-glutamyl-mesodiaminopimelic acid (C12-iE-DAP). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.022
• 作为产物：
  描述：

  在 四(三苯基膦)钯 、 1-羟基苯并三唑 作用下， 生成 N-(9-芴甲氧羰基)-D-谷氨酸 1-叔丁酯
  参考文献：
  名称：

  固相肽合成法合成耐万古霉素肠球菌细胞壁类似物

  摘要：

  直接将d-乳酸锂与2-氯三苯甲基氯树脂直接偶联的简便方法，能够快速有效地固相合成耐万古霉素的肠球菌（VRE）中的细菌细胞壁前体类似物（depsipepteptides）。

  DOI：

  10.1016/s0040-4039(97)01110-6

文献信息

• 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。
• [EN] PROTEIN CONJUGATES<br/>[FR] CONJUGUÉS DE PROTÉINES
  申请人：NOVO NORDISK AS

  公开号：WO2017055582A1

  公开（公告）日：2017-04-06

  The invention relates to protein conjugates and in particular conjugates of more than two protein or polypeptides. The compounds include a trivalent linker moiety that enables efficient production of desired products.

  这项发明涉及蛋白质共轭物，特别是两个以上蛋白质或多肽的共轭物。这些化合物包括三价连接物基团，能够实现所需产品的高效生产。
• [EN] SILANOL BASED THERAPEUTIC PAYLOADS<br/>[FR] CHARGES UTILES THÉRAPEUTIQUES À BASE DE SILANOL
  申请人：BLINKBIO INC

  公开号：WO2017214491A1

  公开（公告）日：2017-12-14

  Described herein in part are silanol based therapeutic payloads comprising a silanol terminus, a divalent spacer moiety, and a drug moiety capable of effecting a target cell or tissue.

  本文部分描述了基于硅醇的治疗载荷，包括硅醇末端、二价间隔基团和能够影响靶细胞或组织的药物基团。
• 液相汇聚式合成索马鲁肽侧链的方法
  申请人：浙江工业大学

  公开号：CN111253287A

  公开（公告）日：2020-06-09

  一种液相汇聚式合成索马鲁肽侧链1的方法：将原料2‑(2‑氨基乙氧基)乙醇的氨基用R1保护，接着与溴乙酸乙酯发生亲核取代反应，再经酯水解一锅制得化合物4，将化合物4的羧基用R2保护，并脱除R1，得到化合物6，化合物6与芴甲氧羰基‑L‑谷氨酸1‑叔丁酯经缩合反应，得到化合物8，将化合物8的R2脱除，再与化合物6进行偶联反应，得到化合物10，脱除化合物10的Fmoc，再与18‑(叔丁氧基)‑18氧代十八烷酸进行酰胺化缩合偶联反应，得到化合物13，化合物13脱除R2，得到产物1；本发明方法合成过程有效、可控、低成本高产率，可适用于放大生产；
• Chiral acidic amino acids as tethers for intramolecular glycosylation
  作者：Katsuya Fukushima、Takashi Kikuma、Yoichi Takeda

  DOI：10.1080/07328303.2021.2015364

  日期：2021.7.24

  Abstract Intramolecular glycosylation with peptides as tethers is attractive for the synthesis of oligosaccharides because conjugation between the amino acids present in the tethers is facile. However, few studies have been published about the effects of the amino acid side chain length and amino acid chirality on the glycosylation process. In this study, we revealed that the chain length of the amino

  摘要 以肽作为系链的分子内糖基化对于寡糖的合成具有吸引力，因为存在于系链中的氨基酸之间的缀合是容易的。然而，很少有关于氨基酸侧链长度和氨基酸手性对糖基化过程的影响的研究发表。在这项研究中，我们发现氨基酸的链长可以调节糖基化过程的区域选择性，这是基于我们观察到当系链是具有彼此连接的天冬氨酸残基的那些时，优选 1,2 连接的产物，而对于基于谷氨酸的系链，1,3-连接的产品是优选的。然而，发现氨基酸手性对糖基化反应的产率和立体选择性没有影响。