478183-70-9

Basic information

• Product Name: FMOC-D-2-NITROPHENYLALANINE
• 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
• CAS NO: 478183-70-9
• Molecular Formula: C24H20N2O6
• Molecular Weight: 432.43
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives
• Mol File: 478183-70-9.mol

Chemical Properties

• Boiling Point: 672.7 °C at 760 mmHg
• Flash Point: 360.6 °C
• Appearance: /
• Density: 1.371±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 5.18E-19mmHg at 25°C
• Refractive Index: 1.649
• Storage Temp.: Store at?0-5°C
• PKA: 3.58±0.11(Predicted)
• CAS DataBase Reference: FMOC-D-2-NITROPHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-2-NITROPHENYLALANINE(478183-70-9)
• EPA Substance Registry System: FMOC-D-2-NITROPHENYLALANINE(478183-70-9)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 478183-70-9(Hazardous Substances Data)

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 FMOC-D-2-NITROPHENYLALANINE 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.

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

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 1991-82-8 (2S)-2-amino-3-(2-nitrophenyl)propanoic acid 

Relevant articles and documents

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

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.