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FMOC-D-2-NITROPHENYLALANINE is a chemical compound that features a phenylalanine amino acid with a 2-nitro group and a FMOC protecting group. FMOC-D-2-NITROPHENYLALANINE is recognized for its role as a building block in peptide synthesis, where it can be linked to other amino acids to create peptides. The FMOC protecting group is advantageous due to its ability to be removed under mild conditions, which is particularly useful in solid-phase peptide synthesis. Additionally, the 2-nitro group on the phenylalanine moiety offers a site for potential further modifications and can influence the biological activity of the synthesized peptide. FMOC-D-2-NITROPHENYLALANINE is widely utilized in research and pharmaceutical development for crafting bioactive peptides.

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  • 478183-70-9 Structure
  • Basic information

    1. Product Name: FMOC-D-2-NITROPHENYLALANINE
    2. Synonyms: (R)-N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-2-AMINO-3-(2-NITRO-PHENYL)-PROPIONIC ACID;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-D-(2-NITROPHENYL)ALANINE;FMOC-D-2-NITROPHE;FMOC-D-2-NITROPHENYLALANINE;FMOC-D-PHE(2-NO2)-OH;FMOC-2-NITRO-D-PHENYLALANINE;2-Nitro-D-phenylalanine, N-FMOC protected;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(2-nitrophenyl)propanoic acid
    3. CAS NO:478183-70-9
    4. Molecular Formula: C24H20N2O6
    5. Molecular Weight: 432.43
    6. EINECS: N/A
    7. Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives
    8. Mol File: 478183-70-9.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 672.7 °C at 760 mmHg
    3. Flash Point: 360.6 °C
    4. Appearance: /
    5. Density: 1.371±0.06 g/cm3 (20 ºC 760 Torr)
    6. Vapor Pressure: 5.18E-19mmHg at 25°C
    7. Refractive Index: 1.649
    8. Storage Temp.: Store at?0-5°C
    9. Solubility: N/A
    10. PKA: 3.58±0.11(Predicted)
    11. CAS DataBase Reference: FMOC-D-2-NITROPHENYLALANINE(CAS DataBase Reference)
    12. NIST Chemistry Reference: FMOC-D-2-NITROPHENYLALANINE(478183-70-9)
    13. EPA Substance Registry System: FMOC-D-2-NITROPHENYLALANINE(478183-70-9)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 478183-70-9(Hazardous Substances Data)

478183-70-9 Usage

Uses

Used in Pharmaceutical Development:
FMOC-D-2-NITROPHENYLALANINE is used as a building block for the synthesis of bioactive peptides, which are crucial for developing new drugs with specific therapeutic effects. FMOC-D-2-NITROPHENYLALANINE's ability to be modified and its role in peptide synthesis make it a valuable asset in the creation of peptides with tailored biological activities.
Used in Research Applications:
In research settings, FMOC-D-2-NITROPHENYLALANINE is utilized as a component in the study of peptide synthesis methods and the exploration of the effects of different modifications on peptide properties. Its presence in the synthesis process allows researchers to investigate the impact of the 2-nitro group and the FMOC protecting group on the structure, stability, and function of the resulting peptides.
Used in Solid-Phase Peptide Synthesis:
FMOC-D-2-NITROPHENYLALANINE is used as a key component in solid-phase peptide synthesis, a technique that facilitates the stepwise assembly of peptides. The mild conditions required for the removal of the FMOC protecting group make this compound particularly suitable for this method, contributing to the efficiency and versatility of peptide synthesis.
Used in the Synthesis of Modified Peptides:
The 2-nitro group on FMOC-D-2-NITROPHENYLALANINE provides a site for further chemical modifications, which can alter the properties and functions of the peptides in which it is incorporated. This feature is exploited in the synthesis of modified peptides with enhanced or novel biological activities, potentially leading to the development of new therapeutic agents.

Check Digit Verification of cas no

The CAS Registry Mumber 478183-70-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 4,7,8,1,8 and 3 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 478183-70:
(8*4)+(7*7)+(6*8)+(5*1)+(4*8)+(3*3)+(2*7)+(1*0)=189
189 % 10 = 9
So 478183-70-9 is a valid CAS Registry Number.
InChI:InChI=1/C24H20N2O6/c27-23(28)21(13-15-7-1-6-12-22(15)26(30)31)25-24(29)32-14-20-18-10-4-2-8-16(18)17-9-3-5-11-19(17)20/h1-12,20-21H,13-14H2,(H,25,29)(H,27,28)/t21-/m1/s1

478183-70-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name Fmoc-2-nitro-D-phenylalanine

1.2 Other means of identification

Product number -
Other names FMOC-D-2-NITROPHENYLALANINE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:478183-70-9 SDS

478183-70-9Downstream Products

478183-70-9Relevant articles and documents

Wavelength-Selective Uncaging of Two Different Photoresponsive Groups on One Effector Molecule for Light-Controlled Activation and Deactivation

Abdellaoui, Chahinez,Bains, Jasleen Kaur,Elamri, Isam,Gande, Santosh Lakshmi,Hohmann, Katharina Felicitas,Schwalbe, Harald,Stirnal, Elke,Wachtveitl, Josef

supporting information, p. 10596 - 10603 (2021/07/28)

Photocleavable protecting groups (PPGs) play a pivotal role in numerous studies. They enable controlled release of small effector molecules to induce biochemical function. The number of PPGs attached to a variety of effector molecules has grown rapidly in recent years satisfying the high demand for new applications. However, until now molecules carrying PPGs have been designed to activate function only in a single direction, namely the release of the effector molecule. Herein, we present the new approach Two-PPGs-One-Molecule (TPOM) that exploits the orthogonal photolysis of two photoprotecting groups to first release the effector molecule and then to modify it to suppress its induced effect. The moiety resembling the tyrosyl side chain of the translation inhibitor puromycin was synthetically modified to the photosensitive ortho-nitrophenylalanine that cyclizes upon near UV-irradiation to an inactive puromycin cinnoline derivative. Additionally, the modified puromycin analog was protected by the thio-coumarylmethyl group as the second PPG. This TPOM strategy allows an initial wavelength-selective activation followed by a second light-induced deactivation. Both photolysis processes were spectroscopically studied in the UV/vis- and IR-region. In combination with quantum-chemical calculations and time-resolved NMR spectroscopy, the photoproducts of both activation and deactivation steps upon illumination were characterized. We further probed the translation inhibition effect of the new synthesized puromycin analog upon light activation/deactivation in a cell-free GFP translation assay. TPOM as a new method for precise triggering activation/deactivation of effector molecules represents a valuable addition for the control of biological processes with light.

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