Fmoc-12-氨基十二烷酸 | 128917-74-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - FMOC-氨基酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: Fmoc-12-氨基十二烷酸
• 中文别名: FMOC-12-氨基十二烷酸；12-(Fmoc-氨基)十二烷酸
• 英文名称: 9-fluorenylmethoxycarbonyl-12-aminododecanoic acid
• 英文别名: Fmoc-12-aminododecanoic acid；12-(Fmoc-amino)dodecanoic acid；12-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)dodecanoic acid；Fmoc-12-Ado-OH；12-(9H-fluoren-9-ylmethoxycarbonylamino)dodecanoic acid
• CAS: 128917-74-8
• 化学式: C₂₇H₃₅NO₄
• 分子量: 437.579
• InChiKey: HVGIKYAQSSNFCH-UHFFFAOYSA-N

物化性质

• 熔点：
  102 °C
• 沸点：
  628.8±28.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 安全说明：
  S22
• WGK Germany：
  3
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储温度应保持在0°C。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Fmoc-12-ado-oh
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: Fmoc-12-ado-oh
CAS number: 128917-74-8

---

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.

---

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.

---

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.

---

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:

---

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: C27H35NO4
Molecular weight: 437.6

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  Fmoc-12-氨基十二烷酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (9H-fluoren-9-yl)methyl (12-chloro-12-oxododecyl)carbamate
  参考文献：
  名称：

  Primary Amine Tethered Small Molecules Promote the Degradation of X-Linked Inhibitor of Apoptosis Protein

  摘要：

  DOI：

  10.1021/jacs.1c05269
• 作为产物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 12-氨基十二酸 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 20.0h， 以43%的产率得到Fmoc-12-氨基十二烷酸
  参考文献：
  名称：

  通过固相合成制备酶活化毒胡萝卜素前药。

  摘要：

  由于实体瘤中的细胞分裂速度不如骨髓中的细胞或免疫系统细胞，因此有丝分裂抑制剂在用于治疗前列腺癌和乳腺癌等疾病时通常会引起严重的副作用。克服这个问题的一种方法是尝试开发基于一般细胞毒素的药物，如加利车霉素和毒胡萝卜素，它们在细胞周期的所有阶段杀死细胞。然而，只有在可能有效靶向恶性组织时才能使用此类毒素。在毒胡萝卜素的情况下，通过将药物与仅在肿瘤附近裂解的肽结合以释放细胞毒性药物或具有保留活性的类似物来实现对肿瘤相关细胞的选择性。

  DOI：

  10.3390/molecules23061463

文献信息

• Pd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors
  作者：Bichao Song、Peipei Xie、Yingzi Li、Jiping Hao、Lu Wang、Xiangyang Chen、Zhongliang Xu、Haitian Quan、Liguang Lou、Yuanzhi Xia、K. N. Houk、Weibo Yang

  DOI：10.1021/jacs.0c00078

  日期：2020.6.3

  The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadiene, represents a great challenge in organic synthesis. Herein, we wish to report a distinctive Pd(0) car-bene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl benzoxazinones

  多取代丁二烯尤其是多功能丁二烯的高效立体选择性合成是有机合成中的一大挑战。在此，我们希望报告一种独特的 Pd(0) 碳烯引发的脱羧烯化方法，该方法能够将重氮酯与乙烯基碳酸亚乙酯 (VEC)、乙烯基恶唑烷酮或乙烯基苯并恶嗪酮直接偶联，以提供醇、胺或苯胺。含有 1,3-二烯，产率中等至高，具有出色的立体选择性。该协议具有操作简单、反应条件温和、底物范围广泛和可扩展性等特点。值得注意的是，分离并表征了一种结构独特的烯丙基 Pd(II) 中间体。DFT 计算和控制实验表明，稀有的 Pd(0) 卡宾中间体可能参与该反应。此外，作为新型构件的多取代丁二烯前所未有地组装成大环化合物，有效抑制了 P-糖蛋白 (P-gp)，并以 190 倍的速度显着逆转了癌细胞的多药耐药性。
• A convenient procedure for the solid-phase synthesis of hydroxamic acids on PEGA resins
  作者：Nitin S. Nandurkar、Rico Petersen、Katrine Qvortrup、Vitaly V. Komnatnyy、Kennedy M. Taveras、Sebastian T. Le Quement、Robin Frauenlob、Michael Givskov、Thomas E. Nielsen

  DOI：10.1016/j.tetlet.2011.10.103

  日期：2011.12

  An efficient method for the solid-phase synthesis of hydroxamic acids is described. The method comprises the nucleophilic displacement of esters immobilized on PEGA resins with hydroxylamine/sodium hydroxide in isopropanol. The hydroxyaminolysis protocol is compatible with a broad range of PEGA-supported peptide and peptidomimetic esters. The methodology was found to be compatible with two new strategies

  描述了一种固相合成异羟肟酸的有效方法。该方法包括用羟胺/氢氧化钠在异丙醇中固定在PEGA树脂上的酯进行亲核取代。羟氨解方案可与多种PEGA支持的肽和拟肽酯相容。发现该方法与分别用于合成固载内酰胺和二酮哌嗪的两种新策略兼容，二者均依赖于环状N-酰基亚胺离子与富电子芳族化合物和杂芳族化合物的高分子间和分子内反应性，最终提供了高纯度的异羟肟酸衍生物。
• A New Synthesis of Lysophosphatidylcholines and Related Derivatives. Use of <i>p</i>-Toluenesulfonate for Hydroxyl Group Protection
  作者：Renato Rosseto、Niloufar Bibak、Rosemarie DeOcampo、Trishul Shah、Ara Gabrielian、Joseph Hajdu

  DOI：10.1021/jo062352f

  日期：2007.3.1

  The synthesis is based upon (1) the use of 3-p-toluenesulfonyl-sn-glycerol to provide the stereocenter for construction of the optically active lysophospholipid molecule, (2) tetrahydropyranylation of the secondary alcohol function to achieve orthogonal protection of the sn-2- and sn-3-glycerol positions, and (3) elaboration of the phosphodiester headgroup using a 2-chloro-1,3,2-dioxaphospholane/trimethylamine

  报道了溶血磷脂酰胆碱的新的立体选择性合成。合成是基于（1）利用3- p -toluenesulfonyl- SN -甘油一种用于施工光学活性溶血磷脂分子的提供立构，（2）二级醇官能的tetrahydropyranylation来实现的正交保护SN - 2-和sn -3-甘油位置，以及（3）使用2-氯-1,3,2-二氧杂膦环/三甲胺序列精制磷酸二酯头基。在进行合成的过程中，发现sn -3- p的甲氧基乙酸酯置换-甲苯磺酸酯产生反应性甲氧基乙酰基酯，其随后可以用甲醇/叔丁胺选择性地裂解，而在sn -1位的酯基保持不受影响。已显示该序列适合于制备经光谱标记的溶血磷脂酰胆碱。这些化合物之一很容易转化为双标记的混合链磷脂酰胆碱，可用于脂解酶的实时荧光共振能量转移（FRET）分析。此外，这项工作还导致了新的合成策略，该策略基于在存在其他碱不稳定基团（例如FMOC衍生物）的情况下对甲苯磺酰基的化学选择性
• Synthesis of phosphatidylcholine analogues derived from glyceric acid: a new class of biologically active phospholipid compounds
  作者：Renato Rosseto、Celize M. Tcacenco、Radha Ranganathan、Joseph Hajdu

  DOI：10.1016/j.tetlet.2008.03.084

  日期：2008.5

  Synthesis of a new class of phosphatidylcholine analogues derived from glyceric acid is reported for spectroscopic studies of phospholipases and conformation of phospholipid side-chains in biological membranes, using fluorescence resonance energy transfer (FRET) techniques.

  据报道，使用荧光共振能量转移 (FRET) 技术合成了一类新的源自甘油的磷脂酰胆碱类似物，用于磷脂酶和生物膜中磷脂侧链构象的光谱研究。
• Synthesis of phospholipids on a glyceric acid scaffold: design and preparation of phospholipase A2 specific substrates
  作者：Renato Rosseto、Joseph Hajdu

  DOI：10.1016/j.tet.2014.03.054

  日期：2014.5

  Synthesis of a new series of phospholipid analogues to serve as activity-based probes of secretory phospholipase A2 enzymes is reported. The synthesis is based upon (1) preparation of long-chain esters and amides of glyceric acid, followed by (2) regioselective derivatization of the diol function of the molecule to achieve phosphorylation at the primary hydroxyl group, and to introduce the incipient

  合成了一系列新的磷脂类似物，用作分泌型磷脂酶 A 2酶的活性探针。该合成基于 (1) 甘油酸的长链酯和酰胺的制备，然后 (2) 分子的二醇官能团的区域选择性衍生化以实现伯羟基的磷酸化，并引入初始的sn -目标化合物的2-酯基团。该序列已被证明允许掺入荧光、顺磁性和氧化还原活性报告基团，从而产生适用于检测和测量酶活性的磷脂类似物，以开发高度特异性、实时的磷脂酶 A 2光谱分析酶，以及跟踪水解产物的代谢归宿。该合成方法具有很大的灵活性，为其他磷脂代谢酶的活性探针的设计和合成开辟了道路。