Boc-Met-Leu-Phe-OH | 67247-12-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Boc-Met-Leu-Phe-OH
• 英文别名: Boc-MLF；Boc-Met-Leu-Phe；(2S)-2-[[(2S)-4-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-methylsulfanylbutanoyl]amino]pentanoyl]amino]-3-phenylpropanoic acid
• CAS: 67247-12-5
• 化学式: C₂₅H₃₉N₃O₆S
• mdl: MFCD00037435
• 分子量: 509.667
• InChiKey: GYBXWOPENJVQKE-UFYCRDLUSA-N

物化性质

• 溶解度：
  在 DMSO 中的溶解度为 2 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  159
• 氢给体数：
  4
• 氢受体数：
  7

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-Met-Leu-Phe-OH
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: Boc-Met-Leu-Phe-OH
CAS number: 67247-12-5

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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, 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: C25H39N3O6S
Molecular weight: 509.7

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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, sulfur 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：

  Boc-Met-Leu-Phe-OH 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.67h， 生成 Ac-MLF-β-ala-OSu
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF FUNGAL INFECTIONS
  [FR] COMPOSITIONS ET MÉTHODES POUR LE TRAITEMENT D'INFECTIONS FONGIQUES

  摘要：

  公开号：

  WO2015035102A3
• 作为产物：
  描述：

  甲基(2S)-2-[[(2S)-4-甲基-2-[[(2S)-2-[(2-甲基丙烷-2-基)氧基羰基氨基]-4-甲硫基丁酰基]氨基]戊酰]氨基]-3-苯丙酸酯 在 phosphate buffer 作用下， 以 叔丁醇 为溶剂， 以80%的产率得到Boc-Met-Leu-Phe-OH
  参考文献：
  名称：

  Chemo-Enzymatic Synthesis of Fmoc-Peptide Fragments

  摘要：

  Optically pure Fmoc-peptide fragments have been prepared via dicyclohexylcarbodiimide coupling of N-protected amino acids with amino acid esters, followed by enzyme-catalyzed ester hydrolysis by alcalase with a high concentration of organic solvent in a high yield.

  DOI：

  10.1080/00397919208055416
• 作为试剂：
  描述：

  N,N'-二环己基碳二亚胺 在 Boc-Met-Leu-Phe-OH 、 1-羟基苯并三唑 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N,N-二环己脲
  参考文献：
  名称：

  合成金枪鱼多聚体取代肽的生物活性研究

  摘要：

  丹斯乐但D'étudier乐phénomène德clustérisationDESrécepteursmembranaires，知性rapportons拉德SYNTHESE新贵导出tétraazacycloalkanessubstitués帕L'intermédiaireD'intercalateurs一个DES肽（ñ -甲酰基的Met-LEU-Phe的生产）biologiquement actifs。

  DOI：

  10.1002/jhet.5570220532

文献信息

• Phase-transfer reagents as C-terminal protecting groups; facile incorporation of free amino acids or peptides into peptide sequences
  作者：Shui-Tein Chen、Kung-Tsung Wang

  DOI：10.1039/c39900001045

  日期：——

  Phase-transfer reagents (basic, neutral, and acidic) can effect temporary protection of carboxy groups by salt formation in C-terminal free amino acids or peptides during peptide synthesis; the use of acidic or neutral phase-transfer reagents as the C-terminal protecting group will not affect the nucleophilicity of the amino group of the salts thus prepared in an organic solvent.

  相转移试剂（碱性，中性和酸性）可通过在肽合成过程中在C端游离氨基酸或肽中形成盐来暂时保护羧基。使用酸性或中性相转移试剂作为C-末端保护基不会影响在有机溶剂中如此制得的盐的氨基的亲核性。
• Efficient preparation of chiral diamines via Red-Al reduction of N-Boc-protected amino acid-derived secondary amides
  作者：Eric A. Voight、Matthew S. Bodenstein、Norihiro Ikemoto、Michael H. Kress

  DOI：10.1016/j.tetlet.2006.01.056

  日期：2006.3

  reduction of N-Boc-protected amino acid-derived secondary amides, avoiding the formation of overreduction and cyclic urea byproducts. The method is showcased by the efficient formal synthesis of NK-1 antagonist LY303870.

  已经开发了选择性还原N -Boc保护的氨基酸衍生的仲酰胺的条件，从而避免了过度还原和环状脲副产物的形成。NK-1拮抗剂LY303870的有效形式合成证明了该方法。
• Stereoselective Oxidative Bioconjugation of Amino Acids and Oligopeptides to Aldehydes
  作者：Henriette N. Tobiesen、Lars A. Leth、Marc V. Iversen、Line Næsborg、Søren Bertelsen、Karl Anker Jørgensen

  DOI：10.1002/anie.202008513

  日期：2020.10.12

  stereoselective, near‐equimolar, and metal‐free oxidative bioconjugation of amino acids and oligopeptides to aldehydes is presented. Based on a newly developed organocatalytic oxidative concept, the C‐terminal and side‐chain carboxylic acid functionalities of amino acids and oligopeptides are shown to couple in a stereoselective manner to α‐branched aldehydes catalyzed by a chiral primary amine and a quinone as

  提出了氨基酸和寡肽与醛的第一个立体选择性，近等摩尔和无金属的氧化生物共轭反应。基于新近开发的有机催化氧化概念，氨基酸和寡肽的C末端和侧链羧酸官能团以立体选择性方式与手性伯胺和醌作为氧化剂催化的α-支化醛偶联。 。氧化偶合通常以高产率进行。对于天冬氨酸，根据保护策略，证明了侧链或C末端羧酸的选择性偶联。立体选择性，氧化生物共轭概念扩展到一系列寡肽，其中呈现了与羧酸官能团的偶联。通过将氧化偶联策略与点击概念合并，可获得用于进一步功能化的生物正交连接分子。已证明，新的立体中心的构型仅由有机催化剂决定。
• COMPOSITIONS AND METHODS FOR THE TREATMENT OF FUNGAL INFECTIONS
  申请人：CIDARA THERAPEUTICS, INC

  公开号：US20160213742A1

  公开（公告）日：2016-07-28

  Compositions and methods for the treatment of fungal infections including compounds containing a pathogen pattern recognition receptor ligand and a β 1,3-glucan synthase inhibitor are disclosed. In particular, compounds containing a lipopeptide moiety and a formyl peptide receptor ligand can be used in the treatment of fungal infections caused by a fungus of the genus Aspergillus or Candida.

  本发明涉及用于治疗真菌感染的组合物和方法，其中包括含有病原体模式识别受体配体和β 1,3-葡聚糖合成酶抑制剂的化合物。特别地，含有脂肽基团和甲酰肽受体配体的化合物可用于治疗由曲霉属或白色念珠菌属真菌引起的真菌感染。
• Chemo-Enzymatic Synthesis of Optically Active Amino Acids and Peptides
  作者：Shui-Tein Chen、Kung-Tsung Wang

  DOI：10.1002/jccs.199900046

  日期：1999.6

  AbstractThe industrial alkaline protease, alcalase, is stable and active in a high concentration of organic solvents and useful as a biocatalyst for (i) diastereoselective hydrolysis of peptide esters and preparation of racemization‐free peptides; (ii) selective incorporation of esters of D‐amino acid into peptides in t‐butanol via a selective hydrolysis of esters of D,L‐amino acid, followed by using the unhydrolyzed D‐esters as a nucleophile in a kinetically controlled peptide bond formation; (iii) resolution of esters of amino acid in 95% t‐butanol/5% water, followed by saponification of the unreacted esters to offer both enantiomers with high yield and optical purity; (iv) completely resolve amino‐acid esters with high yield and optical purity via in situ racemization of the unreacted antipode catalyzed by pyridoxal 5‐phosphate; (v) cryobioorganic synthesis of peptides with increased yields 15%–40% of peptide bond formation by reaction at 5 °C instead of 25–30 °C of a kinetically controlled enzymatic reaction in alcohols.