FMOC-L-Alpha-氨基己二酸-δ-t-丁酯 | 159751-47-0

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: FMOC-L-Alpha-氨基己二酸-δ-t-丁酯
• 中文别名: (S)-2-芴甲氧羰基氨基己二酸6-叔丁酯；(S)-2-FMOC-氨基己二酸6-叔丁酯；(S)-2-Fmoc-氨基己二酸6-叔丁酯；FMOC-L-Α-氨基己二酸-Δ-T-丁酯；(S)-2-芴甲氧羰基氨基己二酸 6-叔丁酯
• 英文名称: Fmoc-Aad(O-t-Bu)-OH
• 英文别名: FmocAad(tBu)OH；(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-(tert-butoxy)-6-oxohexanoic acid；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[(2-methylpropan-2-yl)oxy]-6-oxohexanoic acid
• CAS: 159751-47-0
• 化学式: C₂₅H₂₉NO₆
• 分子量: 439.508
• InChiKey: FFLAQPKWVSSKJC-NRFANRHFSA-N

物化性质

• 熔点：
  108-112°C
• 沸点：
  625.5±50.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Fmoc-Aad(otBu)-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-Aad(otBu)-OH
CAS number: 159751-47-0

---

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, refrigerated.
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: C25H29NO6
Molecular weight: 439.5

---

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

制备方法与用途

简介

(S)-2-芴甲氧羰基氨基己二酸6-叔丁酯，即S-(6-叔丁氧羰基)-α-(N-Fmoc-)氨基己酸，是一种非天然氨基酸。这类化合物不仅是重要药物的关键组成部分，也是众多药物结构中的关键单元。在基因工程药物、预防或治疗用疫苗、核酸药物以及小分子多肽药物等生物药物和疫苗的研究中有着广泛的应用。

用途

(S)-2-芴甲氧羰基氨基己二酸6-叔丁酯作为一种氨基酸衍生物，常被用作医药中间体，广泛应用于医药合成和医药实验研究。

反应信息

• 作为反应物：
  描述：

  FMOC-L-Alpha-氨基己二酸-δ-t-丁酯 在 氯化铵 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以76%的产率得到tert-butyl (S)-5-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-amino-6-oxohexanoate
  参考文献：
  名称：

  [EN] IMMUNOMODULATORS
  [FR] IMMUNOMODULATEURS

  摘要：

  本公开提供了新型大环肽，其抑制PD-1 / PD-L1和PD-L1 / CD80蛋白质/蛋白质相互作用，因此可用于改善各种疾病，包括癌症和传染性疾病。

  公开号：

  WO2016057624A1
• 作为产物：
  描述：

  Fmoc-L-烯丙基甘氨酸 在 palladium on activated charcoal RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 氢气 、 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 FMOC-L-Alpha-氨基己二酸-δ-t-丁酯
  参考文献：
  名称：

  Convenient Access to Glutamic Acid Side Chain Homologues Compatible with Solid Phase Peptide Synthesis

  摘要：

  Preparation of several side chain length variants of glutamic acid is achieved via olefin cross metathesis of allyl glycine derivatives. The products are suitably protected for direct use in Fmoc solid-phase peptide synthesis, as demonstrated by successful synthesis of test sequences.

  DOI：

  10.1021/ol0520222

文献信息

• [EN] NOVEL RADIOLABELLED CXCR4-TARGETING COMPOUNDS FOR DIAGNOSIS AND THERAPY<br/>[FR] NOUVEAUX COMPOSÉS RADIOMARQUÉS DIAGNOSTIQUES ET THÉRAPEUTIQUES CIBLANT CXCR4
  申请人：PROVINCIAL HEALTH SERVICES AUTHORITY

  公开号：WO2020210919A1

  公开（公告）日：2020-10-22

  This application relates to compounds of Formula (I): [targeting peptide]-N(R1)-X1(R2)L1-[linker]-RX n1 (I). The targeting peptide is cyclo[L-Phe-L-Tyr-L-Lys(iPr)-D-Arg-L-2-Nal-Gly-D-Glu]-L-Lys(iPr). R1 is H or methyl. X1 is an optionally substituted C1-C15 hydrocarbon optionally comprising heteroatoms. R2 is C(O)OH or C(O)NH2. L1 is a linkage (thiolether, amide, maleimide-thiol, triazole). The linker has a net negative charge at physiological pH and is a linear or branched chain of 1-10 units of X2L2 and/or X2(L2)2, wherein: each X2 is, independently, an optionally substituted C1-C15 hydrocarbon optionally comprising heteroatoms; and each L2 is a linkage. The linker optionally further comprises an albumin binder bonded to an L2. Each RX is a radiolabelling group linked through a separate L2, selected from: a metal chelator; a prosthetic group containing trifluoroborate (BF3); or a prosthetic group containing a silicon-fluorine-acceptor moiety. The compounds may be useful for imaging CXCR4-expressing tissues or for treating CXCR4-associated diseases or conditions (e.g. cancer).

  这个应用涉及到Formula (I)的化合物：[靶向肽]-N(R1)-X1(R2)L1-[连接物]-RX n1 (I)。靶向肽是cyclo[L-Phe-L-Tyr-L-Lys(iPr)-D-Arg-L-2-Nal-Gly-D-Glu]-L-Lys(iPr)。R1是H或甲基。X1是一个可选择地取代的含有杂原子的C1-C15烃。R2是C(O)OH或C(O)NH2。L1是一个连接物（硫醚、酰胺、马来酰亚胺-硫醇、三唑）。连接物在生理pH下具有净负电荷，是由1-10个X2L2和/或X2(L2)2的线性或支链构成，其中：每个X2独立地是一个可选择地取代的含有杂原子的C1-C15烃；每个L2是一个连接物。连接物可选择地进一步包括与L2结合的白蛋白结合剂。每个RX是通过单独的L2连接的放射标记基团，选自：金属螯合剂；含三氟硼酸盐（BF3）的假体基团；或含硅-氟受体基团的假体基团。这些化合物可能对于成像CXCR4表达组织或治疗与CXCR4相关的疾病或症状（如癌症）有用。
• Preliminary evaluation of 18F-labeled LLP2A-trifluoroborate conjugates as VLA-4 (α4β1 integrin) specific radiotracers for PET imaging of melanoma
  作者：Áron Roxin、Chengcheng Zhang、Sungjoon Huh、Mathieu L. Lepage、Zhengxing Zhang、Kuo-Shyan Lin、François Bénard、David M. Perrin

  DOI：10.1016/j.nucmedbio.2018.02.005

  日期：2018.6

  groups: ammoniumdimethyl-trifluoroborate (AMBF3) and a new N-pyridinyl-para-trifluoroborate (N-Pyr-p-BF3), both capable of facile aqueous 18F-labeling by isotope exchange (IEX), we present the first PET imaging evaluations of two [18F]R-BF3--PEG2-LLP2A tracers using VLA-4 overexpressing B16-F10 murine melanoma tumor mouse models. RESULTS Here, we demonstrate successful one-step 18F-labeling of both conjugates

  导言跨膜α4β1整联蛋白受体或极晚抗原4（VLA-4）与肿瘤转移和血管生成，化学治疗药物耐药性的发展有关，在多发性骨髓瘤，骨肉瘤，淋巴瘤，白血病和黑色素瘤中过表达。拟肽LLP2A是一种高亲和力配体，对VLA-4的细胞外部分具有特异性，几种结合物已通过NIR荧光，111In-SPECT以及68Ga-和64Cu-PET成像进行了体内评估，但迄今为止，不适用于18F-PET。方法使用两个高度稳定的有机三氟硼酸盐假体基团：二甲基三氟硼酸铵（AMBF3）和新的N-吡啶基-对三氟硼酸盐（N-Pyr-p-BF3），两者均能通过同位素交换（IEX）方便地进行18F水性标记，我们介绍了使用VLA-4过表达B16-F10鼠类黑色素瘤小鼠模型的两个[18F] R- --PEG2-LLP2A示踪剂的首次PET成像评估。结果在这里，我们证明了用湿NCA [18F] F-对两种偶联物成功进行的一步18F标记，在7
• [EN] RADIOLABELED COMPOUNDS TARGETING THE PROSTATE-SPECIFIC MEMBRANE ANTIGEN<br/>[FR] COMPOSÉS RADIOMARQUÉS CIBLANT L'ANTIGÈNE MEMBRANAIRE SPÉCIFIQUE DE LA PROSTATE
  申请人：PROVINCIAL HEALTH SERVICES AUTHORITY

  公开号：WO2020252598A1

  公开（公告）日：2020-12-24

  A compound comprising a prostate specific membrane antigen (PSMA)-targeting moiety of the following formula or of a salt or a solvate thereof. R0 is O or S. Each of R1a, R1b and R1c may be –CO2H, –SO2H, –SO3H, –PO2H, or –PO3H2, for example. R2 may be methylene or a derivative thereof, propylene or a derivative thereof, or a derivative of ethylene, optionally substituted. R3 is a linker. When the PSMA-targeting moiety is linked to a radiolabeling group, the compound may be used as an imaging agent or therapeutic agent for PSMA-expressing diseases/conditions.

  一种化合物，包括以下结构式或其盐或溶剂化合物的前列腺特异性膜抗原（PSMA）靶向基团。R0为O或S。R1a、R1b和R1c中的每一个可以是-CO2H、-SO2H、-SO3H、-PO2H或-PO3H2，例如。R2可以是亚甲基或其衍生物、丙烯基或其衍生物，或乙烯的衍生物，可选择性地取代。R3是一个连接基。当PSMA靶向基团与放射标记基团连接时，该化合物可用作PSMA表达疾病/病况的成像剂或治疗剂。
• Ultra-large chemical libraries for the discovery of high-affinity peptide binders
  作者：Anthony J. Quartararo、Zachary P. Gates、Bente A. Somsen、Nina Hartrampf、Xiyun Ye、Arisa Shimada、Yasuhiro Kajihara、Christian Ottmann、Bradley L. Pentelute

  DOI：10.1038/s41467-020-16920-3

  日期：——

  peptide-based binding molecules, identified by affinity selection. Synthetic libraries can access broader chemical space, but typically examine only ~ 106 compounds by screening. Here we show that in-solution affinity selection can be interfaced with nano-liquid chromatography-tandem mass spectrometry peptide sequencing to identify binders from fully randomized synthetic libraries of 108 members—a 100-fold

  高多样性基因编码组合文库（10 8 -10 13 个成员）是基于肽的结合分子的丰富来源，通过亲和力选择进行鉴定。合成文库可以访问更广泛的化学空间，但通常通过筛选仅检查约 10 6种化合物。在这里，我们展示了溶液内亲和选择可以与纳米液相色谱-串联质谱肽测序相结合，从 10 8 个成员的完全随机合成文库中识别结合物——多样性比标准实践增加了 100 倍。为了验证这种方法，我们证明单克隆抗体的结合物的鉴定与文库多样性成比例，因为多样性从 10 6 –10 8增加。然后将这些结果应用于 MDM2 的 p53 样结合物的发现，以及 3-19 nM 亲和力、基于 α/β-肽的 14-3-3 结合物家族。确定了与 14-3-3σ 复合的这些结合物之一的 X 射线结构，说明了 β-氨基酸在促进关键结合接触中的作用。
• [EN] PEPTIDES FOR ACTIVATION OF CELL SIGNALING IN OSTEOPROGENITOR CELLS<br/>[FR] PEPTIDES POUR L'ACTIVATION DE LA SIGNALISATION CELLULAIRE DANS DES CELLULES OSTÉOPROGÉNITRICES
  申请人：UNIV CALIFORNIA

  公开号：WO2020018941A1

  公开（公告）日：2020-01-23

  The present invention provides compounds and pharmaceutical compositions of peptidomimetic ligands. The peptidomimetic ligands can be conjugated with phosphonate drugs. The compounds and pharmaceutical compositions of the present invention are useful in the treatment of osteoporosis and for the promotion of bone growth due to their specificity for the α4β1 integrin on mesenchymal stem cells and for the surface of bone.

  本发明提供了肽类模拟配体的化合物和制药组合物。这些肽类模拟配体可以与膦酸盐药物结合。本发明的化合物和制药组合物由于其对于骨髓干细胞上的α4β1整合素和骨表面的特异性而可用于治疗骨质疏松症和促进骨生长。