(S)-N-芴甲氧羰基-3-氨基-5-苯基戊酸 | 219967-74-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他氨基酸衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: (S)-N-芴甲氧羰基-3-氨基-5-苯基戊酸
• 中文别名: FMOC-L-3-氨基-5-苯基戊酸；FMOC-(S)-3-氨基-5-苯基戊酸
• 英文名称: (S)-3-(<<(9H-fluoren-9-yl)methoxy>carbonyl>amino)-5-phenylpentanoic acid
• 英文别名: Fmoc-(S)-3-amino-phenylpentanoic acid；(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-phenylpentanoic acid；(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-phenylpentanoic acid
• CAS: 219967-74-5
• 化学式: C₂₆H₂₅NO₄
• 分子量: 415.489
• InChiKey: FYJRCXFXXJMPFO-IBGZPJMESA-N

物化性质

• 熔点：
  176-177 °C
• 沸点：
  657.5±55.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  在指定条件下稳定，远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-(s)-3-amino-5-phenylpentanoic acid
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: Fmoc-(s)-3-amino-5-phenylpentanoic acid
CAS number: 219967-74-5

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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.
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: C26H25NO4
Molecular weight: 415.5

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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：

  (S)-N-芴甲氧羰基-3-氨基-5-苯基戊酸 在 i-PrNEt 、 1-羟基苯并三唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 25.0h， 生成 (S)-2-(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)amino-6-ethylphenyl-5,6-dihydro-4-pyrimidinone
  参考文献：
  名称：

  Syntheses of Guanidinoglycosides with the Inventive use of Mitsunobu Conditions­ and 1,8-Diazabicyclo[5.4.0]undec-7-ene

  摘要：

  我们成功合成了一系列新型胍类糖苷。 通过使用 Mitsunobu 条件作为一种策略，将糖吡喃糖异构羟基转化为相应的取代掩蔽胍类，产量很高。 随后进行脱保护并与 Fmoc 保护的δ-氨基酸偶联，得到了一系列 N,N′-取代的甲基异硫脲。 在一定量的 DBU 催化下，Fmoc 发生裂解并同时发生环化反应，从而得到鸟苷糖苷类化合物。

  DOI：

  10.1055/s-2003-36815
• 作为产物：
  描述：

  Boc-L-高苯丙氨酸 在 N-甲基吗啉 、 水 、 silver trifluoroacetate 、 sodium carbonate 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 三乙胺 、 丙酮 为溶剂， 反应 11.33h， 生成 (S)-N-芴甲氧羰基-3-氨基-5-苯基戊酸
  参考文献：
  名称：

  (S)-β3-Homolysine- and (S)-β3-Homoserine-Containingβ-Peptides: CD Spectra in Aqueous Solution

  摘要：

  For further structural studies and for physiological investigations of beta-peptides, it is necessary to have H2O-soluble derivatives. Thus, we have prepared beta-hexa-, beta-hepta-, and beta-nonapeptides (1-6) with two, three, and seven side chains of lysine and serine. To detect possible pi-pi interactions, we also included the beta-amino acid beta(2)-HHop, resulting from homologation of so-called homophenylalanine (Hop) (5 and 6). The Fmoc-beta(2)- and beta(3)-amino-acid derivatives (11-14 and 19), and the corresponding beta-peptides were prepared by methods previously described (solid-phase peptide coupling; HPLC-pure samples, Fig. I). Circular-dichroism spectra (Fig.2) indicate the presence of less pronounced secondary structures (especially of the lysine analogues with multiple positive charge) in H2O as compared to MeOH. The beta(3)-heptapeptide (3) with two serine side chains is well soluble in H2O and exhibits the CD pattern typical of the 3(1)-helical structure.

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2141::aid-hlca2141>3.0.co;2-5

文献信息

• CONJUGATE-BASED ANTIFUNGAL AND ANTIBACTERIAL PRODRUGS
  申请人：Bapat Abhijit S.

  公开号：US20140364595A1

  公开（公告）日：2014-12-11

  The invention provides conjugate-based antifungal or antibacterial prodrugs formed by coupling at least one anti-fungal agent or antibacterial agent with at least one linker and/or carrier. The prodrugs are of formula: (i) (AFA) m -X-(L) n ; (ii) [(AFA) m′ -X] p -L; (iii) AFA-[X-(L) n′ ] q ; or (iv) (AFA) m″ -X, wherein: AFA is an antifungal agent or an antibacterial agent; L is a carrier; X is a linker; m ranges from 1 to 10; n ranges from 2 to 10; m′ is 1 to 10; p is 1 to 10; n′ is 1 to 10; and q is 1 to 10, provided that q′ and n are not both 1; and m″ is 1 to 10. The invention also provides nanoparticles comprising the conjugate-based prodrugs. Additionally, the invention also provides non-conjugated antifungal and antibacterial agents in the form of nanoparticles.

  该发明提供了由至少一种抗真菌剂或抗菌剂与至少一种连接剂和/或载体偶联形成的基于共轭的抗真菌或抗菌前药。这些前药的公式为：(i) (AFA) m -X-(L) n ; (ii) [(AFA) m′ -X] p -L; (iii) AFA-[X-(L) n′ ] q ; 或 (iv) (AFA) m″ -X，其中：AFA是抗真菌剂或抗菌剂；L是载体；X是连接剂；m范围从1到10；n范围从2到10；m′为1到10；p为1到10；n′为1到10；q为1到10，前提是q'和n不同时为1；m″为1到10。该发明还提供了包含基于共轭的前药的纳米粒子。此外，该发明还提供了以纳米粒子形式的非共轭抗真菌和抗菌剂。
• GRAMICIDIN A MUTANTS THAT FUNCTION AS ANTIBIOTICS WITH IMPROVED SOLUBILITY AND REDUCED TOXICITY
  申请人：Trustees of boston College

  公开号：US20150239936A1

  公开（公告）日：2015-08-27

  Described herein are antimicrobial peptides for use in pharmaceutical antibiotic compositions and methods of use thereof. These antimicrobial peptides are Gramicidin A (gA) peptide analogs that, in addition to having potent anti-microbial activity, have greatly increased solubility and significantly reduced toxicity in comparison to the wild-type Gramicidin A peptide.

  本文描述了用于制药抗生素组合物中的抗菌肽及其使用方法。这些抗菌肽是革兰氏阴性杆菌A（gA）肽类似物，除了具有强大的抗微生物活性外，与野生型革兰氏阴性杆菌A肽相比，它们具有极大的溶解性和显著降低的毒性。
• Lin28/let-7 crystal structures, purification protocols, and molecular probes suitable for screening assays and therapeutics
  申请人：PRESIDENT AND FELLOWS OF HARVARD COLLEGE

  公开号：US10000756B2

  公开（公告）日：2018-06-19

  The invention provides compositions and methods for regulating microRNA (miRNA) biogenesis. The invention also relates to compositions and methods for treating or preventing cancer in a subject in need thereof.

  本发明提供了调节微RNA（miRNA）生物发生的组合物和方法。本发明还涉及用于治疗或预防癌症的组合物和方法。
• Modified integrin polypeptides, modified integrin polypeptide dimers, and uses thereof
  申请人：THE CHILDREN'S MEDICAL CENTER CORPORATION

  公开号：US10273283B2

  公开（公告）日：2019-04-30

  Described herein are modified integrin α and/or β headpiece polypeptides, and crystallizable integrin polypeptide dimers comprising a modified integrin α and/or β headpiece polypeptide and a disulfide bond linking the two integrin headpiece polypeptide subunits. Methods for using the modified integrin α and/or β headpiece polypeptides and the integrin polypeptide dimers are also provided herein. For example, methods for characterizing integrin-ligand interaction and identifying integrin ligands are also provided herein. In some embodiments, the identified integrin ligands can be used as inhibitors of integrins.

  本文描述了修饰的整合素α和/或β头多肽，以及可结晶的整合素多肽二聚体，其包含修饰的整合素α和/或β头多肽和连接两个整合素头多肽亚基的二硫键。本文还提供了使用修饰的整合素α和/或β头多肽和整合素多肽二聚体的方法。例如，本文还提供了表征整合素-配体相互作用和鉴定整合素配体的方法。在某些实施方案中，鉴定出的整合素配体可用作整合素的抑制剂。
• Chemical modulators of heat shock protein 70 (Hsp70) by sequential, microwave-accelerated reactions on solid phase
  作者：Susanne Wisén、John Androsavich、Christopher G. Evans、Lyra Chang、Jason E. Gestwicki

  DOI：10.1016/j.bmcl.2007.11.027

  日期：2008.1

  Molecular chaperones, such as Hsp70 and Hsp90, are responsible for a variety of protective, anti-apoptotic functions. While inhibitors of Hsp90, such as geldanamycin and its derivative 17-AAG, are well known and important anti-cancer leads, Hsp70 has received less attention. Interesting lead candidates for Hsp70 share a dihydropyrimidine core; however, the preferred display of pendant functionality is still not clear. Here, we take advantage of the versatility of peptides to explore the requirements for activity. An exploratory compound collection was assembled by performing a Biginelli cyclocondensation at the terminus of a resin-bound beta-peptide. Liberation from solid support yielded peptide-modified dihydropyrimidines and, within this series, we uncovered compounds that alter the ATPase activity of Hsp70 and its bacterial ortholog, DnaK. Moreover, we identified important contributions made by aromatic, hydrophobic groups. These chemical probes could be used to study the roles of this molecular chaperone in disease. (C) 2007 Elsevier Ltd. All rights reserved.