LPFFD | 182912-74-9

• 物质功能分类: 生物化工 - 多肽
• 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: LPFFD
• 英文别名: Leu-Pro-Phe-Phe-Asp；(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-amino-4-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]butanedioic acid
• CAS: 182912-74-9
• 化学式: C₃₃H₄₃N₅O₈
• 分子量: 637.733
• InChiKey: RALAXQOLLAQGTI-IRGGMKSGSA-N

物化性质

• 沸点：
  980.0±65.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO 中≥63.7 mg/mL；乙醇中≥16.33 mg/mL；超声检测水中≥6.9 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  208
• 氢给体数：
  6
• 氢受体数：
  9

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3

SDS

Version 1.2
Regulation (EC) No 1907/2006

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1 - Product and Company Information

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Product Name (PRO18,ASP21)AMYLOID BETA PROTEIN
FRAGMENT (17-21)

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2 - Hazards Identification

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SPECIAL INDICATION OF HAZARDS TO HUMANS AND THE ENVIRONMENT
Not hazardous according to Directive 67/548/EEC.

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3 - Composition/Information on Ingredients

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Product Name CAS # EC no Annex I
Index Number
(PRO18,ASP21)AMYLOID BETA PROTEIN 182912-74-9 None None
FRAGMENT (17-21)
Formula C33H43N5O8
Molecular Weight 637,7300 AMU
Synonyms H-Leu-Pro-Phe-Phe-Asp-OH

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4 - First Aid Measures

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AFTER INHALATION
If inhaled, remove to fresh air. If breathing becomes difficult,
call a physician.
AFTER SKIN CONTACT
In case of skin contact, flush with copious amounts of water for
at least 15 minutes. Remove contaminated clothing and shoes.
Call a physician.
AFTER EYE CONTACT
In case of contact with eyes, flush with copious amounts of
water for at least 15 minutes. Assure adequate flushing by
separating the eyelids with fingers. Call a physician.
AFTER INGESTION
If swallowed, wash out mouth with water provided person is
conscious. Call a physician.
SIGMA www.molbase.com

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5 - Fire Fighting Measures

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EXTINGUISHING MEDIA
Suitable: Water spray. Carbon dioxide, dry chemical powder, or
appropriate foam.
SPECIAL RISKS
Specific Hazard(s): Emits toxic fumes under fire conditions.
SPECIAL PROTECTIVE EQUIPMENT FOR FIREFIGHTERS
Wear self-contained breathing apparatus and protective clothing
to prevent contact with skin and eyes.

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6 - Accidental Release Measures

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PERSONAL PRECAUTION PROCEDURES TO BE FOLLOWED IN CASE OF LEAK OR SPILL
Evacuate area.
PROCEDURE(S) OF PERSONAL PRECAUTION(S)
Wear respirator, chemical safety goggles, rubber boots, and
heavy rubber gloves.
METHODS FOR CLEANING UP
Sweep up, place in a bag and hold for waste disposal. Avoid
raising dust. Ventilate area and wash spill site after material
pickup is complete.

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7 - Handling and Storage

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HANDLING
Directions for Safe Handling: Avoid inhalation. Avoid contact
with eyes, skin, and clothing. Avoid prolonged or repeated
exposure.
STORAGE
Conditions of Storage: Keep tightly closed.
Store at -20°C

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8 - Exposure Controls / Personal Protection

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ENGINEERING CONTROLS
Mechanical exhaust required.
GENERAL HYGIENE MEASURES
Wash thoroughly after handling.
PERSONAL PROTECTIVE EQUIPMENT
Respiratory Protection: Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US)
or CEN (EU). Where risk assessment shows air-purifying respirators
are appropriate use a dust mask type N95 (US) or type P1 (EN 143)
respirator.
Special Protective Measures: Wear appropriate government approved
respirator, chemical-resistant gloves, safety goggles, other
protective clothing.

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9 - Physical and Chemical Properties

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Appearance Physical State: Solid
SIGMA www.molbase.com
Property Value At Temperature or Pressure
pH N/A
BP/BP Range N/A
MP/MP Range N/A
Flash Point N/A
Flammability N/A
Autoignition Temp N/A
Oxidizing Properties N/A
Explosive Properties N/A
Explosion Limits N/A
Vapor Pressure N/A
Partition Coefficient N/A
Viscosity N/A
Vapor Density N/A
Saturated Vapor Conc. N/A
Evaporation Rate N/A
Bulk Density N/A
Decomposition Temp. N/A
Solvent Content N/A
Water Content N/A
Surface Tension N/A
Conductivity N/A
Miscellaneous Data N/A
Solubility N/A

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10 - Stability and Reactivity

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STABILITY
Stable: Stable.
Materials to Avoid: Strong acids, Strong bases.
HAZARDOUS DECOMPOSITION PRODUCTS
Hazardous Decomposition Products: Carbon monoxide, Carbon dioxide,
Nitrogen oxides.
HAZARDOUS POLYMERIZATION
Hazardous Polymerization: Will not occur

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11 - Toxicological Information

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ROUTE OF EXPOSURE
Skin Contact: May cause skin irritation.
Skin Absorption: May be harmful if absorbed through the skin.
Eye Contact: May cause eye irritation.
Inhalation: Material may be irritating to mucous membranes and
upper respiratory tract. May be harmful if inhaled.
Ingestion: May be harmful if swallowed.
CONDITIONS AGGRAVATED BY EXPOSURE
The toxicological properties have not been thoroughly
investigated.

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12 - Ecological Information

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No data available.

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13 - Disposal Considerations

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SIGMA www.molbase.com
SUBSTANCE DISPOSAL
Contact a licensed professional waste disposal service to dispose
of this material. Dissolve or mix the material with a combustible
solvent and burn in a chemical incinerator equipped with an
afterburner and scrubber. Observe all federal, state, and local
environmental regulations.

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14 - Transport Information

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RID/ADR
Non-hazardous for road transport.
IMDG
Non-hazardous for sea transport.
IATA
Non-hazardous for air transport.

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15 - Regulatory Information

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CLASSIFICATION AND LABELING ACCORDING TO EU DIRECTIVES
S-PHRASES: 22-24/25
Do not breathe dust. Avoid contact with skin and eyes.
Not hazardous according to Directive 67/548/EEC.
Caution: Substance not yet fully tested (EU).
COUNTRY SPECIFIC INFORMATION
Germany
WGK: 3
Self-Classification

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16 - Other Information

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WARRANTY
The above information is believed to be correct but does not
purport to be all inclusive and shall be used only as a guide. The
information in this document is based on the present state of our
knowledge and is applicable to the product with regard to
appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Inc.,
shall not be held liable for any damage resulting from handling or
from contact with the above product. See reverse side of invoice
or packing slip for additional terms and conditions of sale.
Copyright 2010 Co. License granted to make
unlimitedpaper copies for internal use only.
DISCLAIMER
For R&D use only. Not for drug, household or other uses.
SIGMA www.molbase.com

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

β-破片肽iAβ5是一种有效的脑淀粉样蛋白β（Aβ）降解剂。阿贝塔沉积与阿尔茨海默病(AD)有关，因为它相关毒性与其β片层构象和/或聚集有关。β-破片肽iAβ5在体内可重复诱导原纤维淀粉样蛋白沉积的分解。因此，这种肽能够预防和/或逆转由Aβ引起的神经元萎缩，并减少围绕Aβ沉积物的白细胞介素-β阳性小胶质细胞样细胞的数量。此外，β-破片肽iAβ5还能减小AD患者大脑中淀粉样斑块的大小和数量。带有疏水性苯甲醇(HBA)标签的β-破片肽iAβ5可用于定量分析，在酸性条件下显示鲜艳的蓝色[1][2][3]。

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 水 为溶剂， 反应 1.0h， 以82%的产率得到LPFFD
  参考文献：
  名称：

  Acid-Triggered Colorimetric Hydrophobic Benzyl Alcohols for Soluble Tag-Assisted Liquid-Phase Synthesis

  摘要：

  Simple screening of acid-triggered reactions of methoxybenzyl alcohols led to the development of a novel colorirnetric hydrophobic benzyl alcohol (HBA) tag. HBA tag-3 (14) retained high solubility in less polar solvents and excellent precipitation properties in polar solvents. Our routine procedure for tag-assisted liquid phase peptide synthesis was applied using HBA tag-3 (14), and an effective synthesis of beta-sheet breaker peptide iA beta 5 (4) was achieved. The tagged peptides showed a vivid blue color under acidic conditions both on TLC plates and in solution, enabling quantitative assay.

  DOI：

  10.1021/acs.orglett.5b02057

文献信息

• Design and synthesis of β-strand-fixed peptides inhibiting aggregation of amyloid β-protein
  作者：Fumiya Tanaka、Kana Shibata、Yoko Monobe、Ken-ichi Akagi、Yuichi Masuda

  DOI：10.1016/j.bmc.2020.115676

  日期：2020.9

  Aggregation of 42-residue amyloid beta-protein (A beta 42) can be prevented by beta-sheet breaker peptides (BSBps) homologous to LVFFA residues, which are included in a beta-sheet region of A beta 42 aggregates. To enhance the affinity of BSBps to the A beta 42 aggregates, we designed and synthesized beta-strand-fixed peptides (BSFps) whose side chains were cross-linked by ring closing metathesis. Conformation analysis verified that the designed peptides could be fixed in beta-strand conformation. Among the synthesized pentapeptides, 1 and 12, whose side chains of 2nd and 4th residues were cross-linked, significantly inhibited the aggregation of A beta 42. This suggested that beta-strand-fixation of BSBps could enhance their inhibitory activity against the A beta 42 aggregation. However, pentapeptides 1 and 12 had little effect on morphology of A beta 42 aggregates (fibrils) and neurotoxicity of A beta 42 against SH-SY5Y cells.
• Development of retro-inverso peptides as anti-aggregation drugs for β-amyloid in Alzheimer's disease
  作者：Balpreet Matharu、Omar El-Agnaf、Amna Razvi、Brian M. Austen

  DOI：10.1016/j.peptides.2010.06.033

  日期：2010.10

  Alzheimer's disease (AD) is a devastating degenerative disorder of the brain for which there is no cure or effective treatment. There is much evidence to suggest that beta-amyloid protein (A beta) aggregation in the brain leading to deposits is an important step in the development of AD. Recently, two peptides, RGKLVFFGR (OR1) and RGKLVFFGR-NH2 (OR2) containing the sequence KLVFF, which is the central region (residues 16-20) of A beta, have been found to be potent inhibitors of A beta aggregate formation. Here we report that retro-inversion of these sequences increases efficacy of the peptides in the inhibition of aggregation and toxicity of beta-amyloid. We describe the synthesis and inhibitory properties of these retro-inverso peptides. (C) 2010 Elsevier Inc. All rights reserved.