N-Fmoc-N’-烯丙氧基羰基-D-赖氨酸 | 214750-75-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 赖氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-Fmoc-N’-烯丙氧基羰基-D-赖氨酸
• 中文别名: N-芴甲氧羰基-N'-烯丙氧基羰基-D-赖氨酸
• 英文名称: Fmoc-D-Lys(Alloc)-OH
• 英文别名: Fmoc-D-Lys(Alloc)；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-(prop-2-enoxycarbonylamino)hexanoic acid
• CAS: 214750-75-1
• 化学式: C₂₅H₂₈N₂O₆
• mdl: MFCD00798639
• 分子量: 452.507
• InChiKey: OJBNDXHENJDCBA-JOCHJYFZSA-N

物化性质

• 沸点：
  689.7±55.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 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：
  2-8°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Fmoc-D-Lys(Alloc)-OH
CAS-No. : 214750-75-1
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No 1272/2008
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
: Nα-Fmoc-Nε-Alloc-D-lysine
Synonyms
Nε-Alloc-Nα-Fmoc-D-lysine
Formula : C25H28N2O6
Molecular Weight : 452,50 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

Fmoc-D-Lys(Aldo)-OH是一种赖氨酸衍生物。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  芴甲氧羰酰基-D-正亮氨酸	Fmoc-D-Nle-OH	112883-41-7	C21H23NO4	353.418
  Fmoc-L-异亮氨酸	Fmoc-Ile-OH	71989-23-6	C21H23NO4	353.418
  Fmoc-L-丙氨酸	N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine	35661-39-3	C18H17NO4	311.337
  Fmoc-甘氨酸	N-(fluoren-9-ylmethoxycarbonyl)glycine	29022-11-5	C17H15NO4	297.31
  Fmoc-L-苯丙氨酸	N-Fmoc L-Phe	35661-40-6	C24H21NO4	387.435
  Fmoc-L-色氨酸	Fmoc-L-Trp	35737-15-6	C26H22N2O4	426.472

反应信息

• 作为反应物：
  描述：

  N-Fmoc-N’-烯丙氧基羰基-D-赖氨酸 在 N-甲基吗啉 、 氯甲酸异丁酯 、 sodium tetrahydroborate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 以80 %的产率得到
  参考文献：
  名称：

  用于树脂上化学功能化的右手和左手伽马肽核酸构建块的开发

  摘要：

  γ 肽核酸 (PNA) 是一类很有前途的核酸模拟物，它采用右旋或左旋螺旋基序作为单链，并以高亲和力和序列特异性与 DNA 或 RNA 杂交，或者根本不杂交，这取决于螺旋意义。它们作为反义和反基因试剂以及分子自组装的构建块很有吸引力；然而，由于其相对较差的生物物理属性和化学修饰的挑战，它们尚未被广泛采用。在这里，我们报告了一组通用单体​​的开发，右手和左手构象异构体各有四种，可实现快速和选择性的树脂上化学功能化和多样化。该系统是模块化的，允许在主链中加入不同的化学基团而不会对杂交产生不利影响。该方法克服了每次在骨架中引入不同化学基团时都需要准备一组新单体的需要。新增加的合成灵活性，以及​​优异的杂交特性、识别正交性和螺旋正义翻译能力，显着扩展了 gamma PNA 在生物学、生物技术和分子工程中的应用范围。

  DOI：

  10.1021/acs.joc.2c01560
• 作为产物：
  描述：

  二甲基丙二胺 、 5-溴氨基苯甲酸甲酯 、 1-碘丁烷 、 3-溴丙烯 、 3-甲氧基溴苄 、 对溴溴苄 、 间硝基苯酚 、 2-氨基对苯二甲酸二甲酯 、 5-硝基-2-甲基苯酚 、 溴甲苯 、 碘乙烷 、 溴乙烷 、 3-溴苄溴 、 4-溴甲基苯甲酸甲酯 、 邻氨基苯甲酸甲酯 、 3-溴戊烷 、 Fmoc-L-色氨酸 、 1-溴戊烷 、 2-碘乙酰胺 、 4-氯苄溴 、 Fmoc-L-苯丙氨酸 、 Fmoc-L-丙氨酸 、 3-溴-2-甲基丙烯 、 N,N-双(3-氨丙基)甲胺 、 乙二胺 、 溴丙烷 、 2-甲基苄溴 、 1,3-丙二胺 、 1,6-己二胺 、 1,5-二氨基戊烷 、 1-羟基苯并三唑 、 4-甲基苄溴 、 溴甲基环丙烷 、 Fmoc-甘氨酸 、 4-硝基间甲苯酚 、 1-溴-2-丁烯 、 3-甲基苄溴 、 2-苯氧乙基溴 、 3-氯苄溴 、 3-硝基溴苄 、 对硝基溴化苄 、 1-溴代异戊烷 、 氯乙酸叔丁酯 、 四亚甲基二胺 、 溴代异丁烷 、 4-溴-1-丁烯 、 1-溴-3-甲基-2-丁烯 、 2-氯苄溴 、 1,4-双(3-氨基丙基)哌嗪 、 1,4-苯二甲胺 、 3-氨基-5-苯基噻吩-2-甲酸甲酯 、 di(1H-imidazol-2-yl)methanethione 、 3-氟溴苄 、 2-氟溴苄 、 4-氟溴苄 、 2-溴乙基膦酸二乙酯 、 trans-1,4-Diaminocyclohexane 、 2-溴乙基乙基醚 、 1,8-二氨基-3,6-二氧杂辛烷 、 Fmoc-L-异亮氨酸 、 2-溴乙基甲基醚 、 1-溴-三氟对二甲苯 、 2-氰基溴苄 、 溴甲基环己烷 、 2-溴溴苄 、 4-叔丁基苄溴 、 3-氨基-2-噻吩甲酸甲酯 、 1-溴-2,2-二甲氧基丙烷 、 芴甲氧羰酰基-D-正亮氨酸 、 环氧溴丙烷 、 2-氨基-4,5-二甲氧基苯甲酸甲酯 、 2,4-二氟溴苄 、 1,3-环己烷二胺 、 3,5-二甲基溴苄 、 氨乙基硫醚 、 甲基2-胺-4-氯苯酚酯 、 3,4-二氟溴苄 、 bromomethyl resin 、 2-甲氧基-5-硝基苯酚 、 3-三氟甲基-4-硝基苯酚 、 3,4,5-三甲氧基氨基苯甲酸甲酯 、 2,5-二甲基-1,4-苯二胺 、 9-fluorenyl-methoxycarbonyl-cyclohexyl alanine 、 (1R,2R)-1,2-diaminocyclohexane 在 哌啶 、 Carbonyldiimidazole 、 tin-2-ethylhexanoate dihydrate 、 potassium tert-butylate 、 水 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N,N'-二异丙基碳二亚胺 、 二溴三苯基膦 作用下， 以 DMF (N,N-dimethyl-formamide) 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 1,2-二氯乙烷 为溶剂， 生成 N-Fmoc-N’-烯丙氧基羰基-D-赖氨酸 、 N-Fmoc-N’-烯丙氧基羰基-D-赖氨酸 、 、 、 、 、 1-hydroxy-3,6-dimethylsulfonamido-8-sulfonate-pyrene 、 、 、 、 、 、 、 6-{[(2S)-methyl-pyrrolidin-2-yl]methyl}-1-(tetrahydro-2H-pyran-4-yl)indoline 、 、 、 、 、 、 3-amino-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4,5-dimethyl-benzamide 、 decaborane 、 、 、 、
  参考文献：
  名称：

  Thioquinazolinone derivatives and combinatorial libraries thereof

  摘要：

  本发明涉及一种新的噻喹唑酮衍生物化合物和以下公式的组合化学库：1其中R1到R4，x和y具有此处提供的含义。

  公开号：

  US20040102629A1

文献信息

• Bis[zinc(ii)dipicolylamino]-functionalised peptides as high affinity receptors for pyrophosphate ions in water
  作者：Karen K. Y. Yuen、Katrina A. Jolliffe

  DOI：10.1039/c3cc40937f

  日期：——

  A library of bis[zinc(II)dipicolylamine]-functionalised linear peptides was prepared using an efficient solid phase peptide synthesis approach and their use as chemosensors for anions in water was investigated using indicator displacement assays. High affinity and selectivity for pyrophosphate (PPi) over adenosine triphosphate (ATP) and adenosine diphosphate (ADP) were observed and additional aromatic side chains provided enhanced discrimination between PPi and ATP.

  通过高效的固相肽合成方法制备了一库功能化有机物bis[锌(II)双吡啶胺]的线性肽，并利用指示剂置换实验研究了它们作为水中阴离子的化学传感器的应用。观察到对焦磷酸盐（PPi）相较于三磷酸腺苷（ATP）和二磷酸腺苷（ADP）具有高亲和力和选择性，而额外的芳香侧链则增强了对PPi和ATP的辨别能力。
• A dual modality^99mTc/Re(<scp>i</scp>)-labelled T140 analogue for imaging of CXCR4 expression
  作者：William L. Turnbull、Lihai Yu、Emily Murrell、Mark Milne、Carlie L. Charron、Leonard G. Luyt

  DOI：10.1039/c8ob01947a

  日期：——

  A T140-derived peptide conjugated with a naphthalimide fluorophore/chelator was coordinated to rhenium or technetium-99m to image CXCR4 expression by fluorescence microscopy or SPECT imaging.

  一种与萘酰亚胺荧光素/螯合剂结合的T140衍生肽被配合到铼或锝-99m上，用于通过荧光显微镜或SPECT成像来成像CXCR4表达。
• Curcumin conjugates for treating and preventing cancers
  申请人：Hansel William

  公开号：US09221877B2

  公开（公告）日：2015-12-29

  Conjugating LHRH to curcumin (LHRH-Curcumin) substantially enhances the bioavailability of curcumin, targets it to cells expressing LHRH receptors, facilitates intravenous administration, and increases the anti-cancer efficacy of curcumin. The conjugate may be used against cancer cells that express the LHRH receptor: pancreas, prostate, breast, testicular, uterine, ovarian, melanoma. LH-Curcumin conjugates may be used against cancer cells that express the LH receptor: prostate, breast, ovary, testis, uterus, pancreas, and melanoma.

  将LHRH与姜黄素结合（LHRH-姜黄素）显著增强了姜黄素的生物利用度，将其靶向表达LHRH受体的细胞，便于静脉给药，并增加了姜黄素的抗癌功效。这种结合物可用于对抗表达LHRH受体的癌细胞：胰腺、前列腺、乳腺、睾丸、子宫、卵巢、黑色素瘤。LH-姜黄素结合物可用于对抗表达LH受体的癌细胞：前列腺、乳腺、卵巢、睾丸、子宫、胰腺和黑色素瘤。
• Design and synthesis of a new orthogonally protected glutamic acid analog and its use in the preparation of high affinity polo-like kinase 1 polo-box domain – binding peptide macrocycles
  作者：David Hymel、Kohei Tsuji、Robert A. Grant、Ramesh M. Chingle、Dominique L. Kunciw、Michael B. Yaffe、Terrence R. Burke

  DOI：10.1039/d1ob01120k

  日期：——

  phospho-dependent PPIs, such as the polo-like kinase 1 (Plk1) polo-box domain (PBD), a phosphorylated protein residue can provide high-affinity recognition and binding to target protein hot spots. Developing antagonists of the Plk1 PBD can be particularly challenging if one relies solely on interactions within and proximal to the phospho-binding pocket. Fortunately, the affinity of phospho-dependent PPI antagonists

  靶向蛋白质-蛋白质相互作用（PPI）已成为抗癌治疗开发的一个重要发现领域。对于磷酸依赖性 PPI，例如 polo 样激酶 1 (Plk1) polo-box 结构域 (PBD)，磷酸化蛋白残基可以提供高亲和力识别并与目标蛋白热点结合。如果仅依赖于磷酸结合袋内部及其附近的相互作用，那么开发 Plk1 PBD 拮抗剂可能会特别具有挑战性。幸运的是，通过利用磷酸结合位点和配体结合时可能揭示的隐藏“神秘”口袋中的相互作用，可以显着增强磷酸依赖性 PPI 拮抗剂的亲和力。在我们当前的论文中，我们描述了针对 Plk1 PBD 的大环肽模拟物的设计和合成，其特征是一种新的谷氨酸类似物，同时充当闭环连接，提供对神秘结合袋的访问，同时在同时实现磷酸苏氨酸 (pT) 残基的正确定向，以在标志性磷酸结合袋中实现最佳相互作用。用这种新的氨基酸类似物制备的大环化合物引入了开链线性母肽中未发现的额外氢键相互作用。值得
• Methods and Compositions for Improved F-18 Labeling of Proteins, Peptides and Other Molecules
  申请人：McBride William J.

  公开号：US20080170989A1

  公开（公告）日：2008-07-17

  The present application discloses compositions and methods of synthesis and use of F-18 labeled molecules of use, for example, in PET imaging techniques. In particular embodiments, the labeled molecules may be peptides or proteins, although other types of molecules including but not limited to aptamers, oligonucleotides and nucleic acids may be labeled and utilized for such imaging studies. In preferred embodiments, the F-18 label may be conjugated to a targeting molecule by formation of a metal complex and binding of the F-18-metal complex to a chelating moiety, such as DOTA, NOTA, DTPA, TETA or NETA. In other embodiments, the metal may first be conjugated to the chelating group and subsequently the F-18 bound to the metal. In other preferred embodiments, the F-18 labeled moiety may comprise a targetable conjugate that may be used in combination with a bispecific or multispecific antibody to target the F-18 to an antigen expressed on a cell or tissue associated with a disease, medical condition, or pathogen. Exemplary results show that F-18 labeled targetable conjugate peptides are stable in human serum at 37° C. for several hours, sufficient time to perform PET imaging analysis.

  本申请公开了合成和使用F-18标记分子的组成物和方法，例如在PET成像技术中使用。在特定实施例中，标记的分子可以是肽或蛋白质，尽管其他类型的分子，包括但不限于aptamer、寡核苷酸和核酸也可以被标记并用于这种成像研究。在优选实施例中，F-18标记可以通过形成金属配合物并将F-18金属配合物结合到螯合基团，例如DOTA、NOTA、DTPA、TETA或NETA，与靶向分子结合。在其他实施例中，金属可以首先与螯合基团结合，然后F-18与金属结合。在其他优选实施例中，F-18标记的分子可以包括可靶向的共轭物，可以与双特异性或多特异性抗体结合使用，以将F-18靶向表达在与疾病、医疗条件或病原体相关的细胞或组织上的抗原。示例结果表明，F-18标记的可靶向共轭肽在37℃的人血清中稳定数小时，足以进行PET成像分析。