芴甲氧羰酰基高苯丙氨酸 | 132684-59-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 芴甲氧羰酰基高苯丙氨酸
• 中文别名: Fmoc-L-高苯丙氨酸；fmoc-高苯丙氨酸；(S)-2-(芴甲氧羰基氨基)-4-苯基丁酸；FMOC-L-高苯丙氨酸；N-FMOC-L-高苯丙氨酸；N-Fmoc-L-高苯基丙氨酸；Fmoc-L-苯基丁氨酸
• 英文名称: N-(fluorenyl-9-methoxycarbonyl)-L-homophenylalanine
• 英文别名: Fmoc-L-homophenylalanine；Fmoc-Homophe-OH；Fmoc-hPhe-OH；Fmoc-homophenylalanine；(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-phenylbutanoic acid；Fmoc-Hfe-OH；Fmoc-hPhe；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-phenylbutanoic acid
• CAS: 132684-59-4
• 化学式: C₂₅H₂₃NO₄
• 分子量: 401.462
• InChiKey: CIHPCIUGLIZADU-QHCPKHFHSA-N

物化性质

• 熔点：
  141.0 to 145.0 °C
• 沸点：
  628.3±50.0 °C(Predicted)
• 密度：
  1.254
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，也未有已知危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 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
• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25
• 危险类别码：
  R36/37/38
• 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：
  密封，在2°C至-8°C下保存

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-L-homophenylalanine
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-L-homophenylalanine
CAS number: 132684-59-4

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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.

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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: C25H23NO4
Molecular weight: 401.5

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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

Fmoc HOphenyl is a derivative of phenylalanine.

反应信息

• 作为反应物：
  描述：

  芴甲氧羰酰基高苯丙氨酸 在 哌啶 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 MorphAc-hPhe-Ala-Tyr(OMe)-3-cyclohexyl-L-Ala-[CH2SO2]-DFMHC
  参考文献：
  名称：

  具有直接荧光信号的用于组成型和免疫蛋白酶体的可调探针

  摘要：

  亲电试剂通常用于抑制蛋白酶。值得注意的是，蛋白酶体抑制剂是细胞存活的关键因素，也是几种FDA批准药物的靶标，其主要特征是亲电头基的反应性。我们旨在通过改变离去基团来调节肽磺酸酯的抑制强度。确实，蛋白酶体抑制与离去基团的p K a密切相关。使用荧光团作为离去基团使我们能够设计探针，该探针在反应后释放化学计量的荧光信号，从而直接将蛋白酶体失活与读数联系起来。该原理可能适用于其他基于磺酰氟的抑制剂，并允许设计用于酶研究的敏感探针。

  DOI：

  10.1002/anie.201605753
• 作为产物：
  描述：

  L-高苯丙氨酸 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 生成 芴甲氧羰酰基高苯丙氨酸
  参考文献：
  名称：

  真菌双加氧酶AsqJ是混杂的且是双峰的：喹诺酮类与喹唑啉酮类的底物定向形成

  摘要：

  先前的研究表明，Fe II /α-酮戊二酸依赖性双加氧酶AsqJ诱导构巢曲霉在viridicatin生物合成中的骨架重排，从苯并[1,4]二氮杂-2,5-二酮底物生成喹诺酮骨架。我们报告说，仅通过改变苯并二氮杂二酮底物中的取代基，AsqJ即可催化另外的，完全不同的反应。通过底物筛选，功能探针的应用和计算分析来建立这种新机制。AsqJ消费税H 2由合适的苯并[1,4]二氮杂-2-5,5-二酮底物的杂环结构生成CO，生成喹唑啉酮。这种新颖的AsqJ催化途径由复杂底物中的单个取代基控制。AsqJ的这种独特的底物定向反应性可实现喹诺酮或喹唑啉酮的靶向生物催化生成，喹诺酮或喹唑啉酮是两种具有特殊生物医学相关性的生物碱框架。

  DOI：

  10.1002/anie.202017086

文献信息

• Synthesis and ABCG2 Inhibitory Activity of Novel Fumitremorgin C Analogs – Specificity and Structure Activity Correlations
  作者：Orsolya Szolomajer-Csikos、Erzsebet Beery、Levente Kosa、Zsuzsanna Rajnai、Marton Jani、Anasztazia Hetenyi、Katalin Tauber Jakab、Peter Krajcsi、Gabor K Toth

  DOI：10.2174/1573406411309040003

  日期：2013.4.1

  The Ko family of fumitremorgin C analogs are potent and selective ABCG2 inhibitors. However, the most potent Ko compounds carry an ester linkage in their side-chain that makes them chemically and metabolically less stable. We have synthesized 16 tricyclic and 28 tetracyclic novel analogs devoid of ester linkages and tested them for ABCG2 inhibition potency and specificity. Unlike in the tricyclic analog group, potent ABCG2 inhibitory compounds were found among the tetracyclic analogs. The most potent compounds carried the 3S,6S,12aS configuration. We observed a marked stereospecificity as compounds with the 3S,6S,12aS configuration were at least 18-fold more potent inhibitors than their diastereoisomeric pairs with a 3S,6R,12aS configuration. This stereospecificity was not observed in ABCB1 and ABCC1 inhibition. Therefore, a single chiral center confers specificity for ABCG2 over ABCB1 and ABCC1. This is quite unexpected considering the large multivalent drug binding site these transporters harbor.

  Ko家族的麹霉素C类似物是强效且具有选择性的ABCG2抑制剂。然而，最强的Ko化合物在其侧链中具有酯键，这使得它们在化学和代谢上不太稳定。我们合成了16种三环化合物和28种四环新类似物，这些类似物不含酯键，并对其ABCG2抑制效力和特异性进行了测试。与三环类似物组不同，在四环类似物中发现了强效ABCG2抑制化合物。最强效的化合物具有3S,6S,12aS构型。我们观察到明显的立体特异性，具有3S,6S,12aS构型的化合物至少比具有3S,6R,12aS构型的差向异构体强18倍。这种立体特异性在ABCB1和ABCC1抑制作用中未见。因此，单一的手性中心赋予了ABCG2相对于ABCB1和ABCC1的特异性。考虑到这些转运蛋白具有的大型多价药物结合位点，这是相当意外的。
• [EN] PEPTIDE LIGANDS FOR BINDING TO MT1-MMP<br/>[FR] LIGANDS PEPTIDIQUES POUR LA LIAISON DE MT1-MMP
  申请人：BICYCLETX LTD

  公开号：WO2018115204A1

  公开（公告）日：2018-06-28

  A peptide ligand specific for MT1 -MMP comprising a polypeptide comprising two diaminopropionic acid (Dap) or N-alkyldiaminopropionic acid (N-AlkDap) residues, and a third residue selected from cysteine, Dap or N-AlkDap, separated by at least two loop sequences, and a molecular scaffold, the peptide being linked to the scaffold by covalent alkylamino linkages with the Dap or N-AlkDap residues of the polypeptide and by covalent thioether linkages with the cysteine when the third residue is cysteine, such that two polypeptide loops are formed on the molecular scaffold, wherein the peptide ligand comprises an amino acid sequence of formula (II): -A1-X1-U/O2-X3-X4-G5-A2-E6-D7-F8-Y9-X10-X11-A3- (SEQ ID NO: 1) (II) or a pharmaceutically acceptable salt thereof; wherein: A1, A2, and A3 are independently cysteine, L-2,3-diaminopropionic acid (Dap), N-beta-alkyl-L-2,3- diaminopropionic acid (N-AlkDap), or N-beta-haloalkyl-L-2,3-diaminopropionic acid (N- HAlkDap), provided that at least one of A1, A2, and A3 is Dap, N-AlkDap or N-HAlkDap; X represents any amino acid residue; U represents a polar, uncharged amino acid residue selected from N, C, Q, M, S and T; and O represents a non-polar aliphatic amino acid residue selected from G, A, I, L, P and V.

  一种特异性结合MT1-MMP的多肽配体，包含一个多肽，该多肽包含两个二氨丙酸（Dap）或N-烷基二氨丙酸（N-AlkDap）残基，以及第三个残基，选自半胱氨酸、Dap或N-AlkDap，通过至少两个环序列隔开，以及一个分子支架，该多肽通过共价烷基氨基连接与多肽的Dap或N-AlkDap残基相连，并且当第三个残基为半胱氨酸时，通过共价硫醚连接与半胱氨酸相连，使得在分子支架上形成两个多肽环，其中多肽配体包含公式（II）的氨基酸序列：-A1-X1-U/O2-X3-X4-G5-A2-E6-D7-F8-Y9-X10-X11-A3-（SEQ ID NO: 1）（II）或其药用可接受的盐；其中：A1、A2和A3独立地为半胱氨酸、L-2,3-二氨丙酸（Dap）、N-β-烷基-L-2,3-二氨丙酸（N-AlkDap）或N-β-卤代烷基-L-2,3-二氨丙酸（N-HAlkDap），前提是至少A1、A2和A3中的一个为Dap、N-AlkDap或N-HAlkDap；X代表任何氨基酸残基；U代表一个极性、不带电的氨基酸残基，选自N、C、Q、M、S和T；O代表一个非极性脂肪族氨基酸残基，选自G、A、I、L、P和V。
• CYCLIC PEPTIDES AND METHODS OF USE THEREOF
  申请人：Regents of the University of Minnesota

  公开号：US20200115416A1

  公开（公告）日：2020-04-16

  Certain embodiments of the invention provide a cyclic compound of formula I: wherein: Pro is a residue of L-proline; X 1 is a residue of Arg or DArg; X 2 is a residue of Phe or DPhe; X 3 is a residue of Phe, DPhe or hPhe; X 4 is a residue of a natural or unnatural amino acid; X 5 is a residue of Ala, Asp, Glu, Lys, His, Phe, Ser, Leu or Gly; X 6 is a residue of Phe, Ala, Gly, Ser, Lys, Asp, Leu, Nle, Trp, Tyr, Cha or hPhe; and DPro is a residue of D-proline; or a salt thereof. Certain embodiments also provide compositions comprising such compounds, as well as methods of using such compounds and compositions.

  发明的某些实施例提供了一个公式I的环状化合物： 其中：Pro是L-脯氨酸的残基；X1是Arg或DArg的残基；X2是Phe或DPhe的残基；X3是Phe、DPhe或hPhe的残基；X4是天然或非天然氨基酸的残基；X5是Ala、Asp、Glu、Lys、His、Phe、Ser、Leu或Gly的残基；X6是Phe、Ala、Gly、Ser、Lys、Asp、Leu、Nle、Trp、Tyr、Cha或hPhe的残基；而DPro是D-脯氨酸的残基；或其盐。某些实施例还提供了包含这种化合物的组合物，以及使用这种化合物和组合物的方法。
• [EN] CYCLOHEXAPEPTIDES AS SELECTIVE SOMATOSTATIN SST5 RECEPTOR AGONISTS<br/>[FR] CYCLOHEXAPEPTIDES EN TANT QU'AGONISTES SÉLECTIFS DU RÉCEPTEUR DE LA SOMATOSTATINE SST5
  申请人：HEPTARES THERAPEUTICS LTD

  公开号：WO2020074926A1

  公开（公告）日：2020-04-16

  The disclosures herein relate to novel compounds of formula (1) : (1) and salts thereof, wherein W, X, Y, Z, m, n, q, R1, R2, R3, R4, R5 and R6 are defined herein, and their use in treating, preventing, ameliorating, controlling or reducing the risk of disorders associated with somatostatin receptors.

  本公开涉及式（1）的新化合物及其盐：（1），其中W、X、Y、Z、m、n、q、R1、R2、R3、R4、R5和R6在此处定义，并其在治疗、预防、改善、控制或减少与生长抑素受体相关的疾病风险方面的用途。
• Design, Synthesis, and Screening of a Library of Peptidyl Bis(Boroxoles) as Oligosaccharide Receptors in Water: Identification of a Receptor for the Tumor Marker TF-Antigen Disaccharide
  作者：Arnab Pal、Marie Bérubé、Dennis G. Hall

  DOI：10.1002/anie.200906620

  日期：2010.2.15

  Mini lectins: A new class of oligosaccharide receptors (see example) was designed by exploiting several modes of molecular recognition, including the unique ability of benzoboroxoles to complex hexopyranosides. The synthesis is modular, thus well suited to targeting specific oligosaccharides using combinatorial libraries.

  迷你凝集素：通过利用多种分子识别模式设计了一种新型的寡糖受体（参见示例），包括苯并环硼烷对复杂的吡喃吡喃糖苷的独特能力。合成是模块化的，因此非常适合使用组合文库靶向特定的寡糖。