95753-55-2

Basic information

• Product Name: Fmoc-4-nitro-L-phenylalanine
• Synonyms: FMOC-4-NITRO PHENYLALANINE;FMOC-4-NITRO-PHE-OH;9-FLUORENYLMETHOXYCARBONYL-P-NITRO-L-PHENYLALANINE;(S)-2-(FLUORENYLMETHOXYCARBONYLAMINO)-3-(4-NITROPHENYL)PROPANOIC ACID;RARECHEM BK PT 0075;N-ALPHA-FMOC-4-NITRO-L-PHENYLALANINE;N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-4-NITRO-L-PHENYLALANINE;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-4-NITROPHENYLALANINE
• CAS NO: 95753-55-2
• Molecular Formula: C₂₄H₂₀N₂O₆
• Molecular Weight: 432.43
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Phenylalanine [Phe, F];Unusual Amino Acids;Fmoc-Amino acid series
• Mol File: 95753-55-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 213-223℃
• Boiling Point: 692.3 °C at 760 mmHg
• Flash Point: 372.5 °C
• Appearance: /
• Density: 1.371 g/cm³
• Storage Temp.: 2-8°C
• Solubility: almost transparency in N,N-DMF
• PKA: 3.59±0.10(Predicted)
• BRN: 5178656
• CAS DataBase Reference: Fmoc-4-nitro-L-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-4-nitro-L-phenylalanine(95753-55-2)
• EPA Substance Registry System: Fmoc-4-nitro-L-phenylalanine(95753-55-2)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 95753-55-2(Hazardous Substances Data)

Usage

Description

Fmoc-4-nitro-L-phenylalanine, also known as Fmoc-Phe(4-NO2)-OH, is a synthetic derivative of the naturally occurring amino acid L-phenylalanine. It is characterized by the presence of a 4-nitro group and a 9-fluorenylmethoxycarbonyl (Fmoc) protecting group. Fmoc-4-nitro-L-phenylalanine is a white powder and is used as a building block in the synthesis of various biologically active molecules.

Uses

Used in Pharmaceutical Industry:
Fmoc-4-nitro-L-phenylalanine is used as a key intermediate in the synthesis of squaric acid derivatives, which act as VLA-4 integrin antagonists. These antagonists are important in the development of drugs targeting inflammatory and autoimmune diseases, as they help regulate cell adhesion and migration processes.
Additionally, Fmoc-4-nitro-L-phenylalanine serves as an intermediate in the synthesis of analogs of kahalalide F, a natural product with potential applications in cancer therapy and other therapeutic areas. The synthesis of these analogs allows for the exploration of novel compounds with improved pharmacological properties and therapeutic potential.

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 63-91-2 L-phenylalanine 

Downstream Products

• 106327-79-1 H-Tyr-D-Orn[*]-Phe(p-NO₂)-D-Asp[*]-NH₂ 
• 95753-56-3 4-amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine 
• 381222-37-3 (2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(4-nitrophenyl)propionic acid tert-butyl ester 

Relevant articles and documents

Synthesis of new tetrazolyl derivatives of L- and D-phenylalanine

New tetrazolyl derivatives of L- and D-phenylalanine were synthesized by azidation of n-propyl esters of (2S)- and (2R)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-aminophenyl)propionic acids and by a series of subsequent chemical transformations. The structure and individuality of the compounds obtained were confirmed by using a complex of spectral and chromatographic methods.

α,α-difluorophosphonomethyl azobenzene derivatives as photoregulated phosphoamino acid analogs. 1. Design and synthesis

A series of novel, photoregulated phosphoamino acid analogs based on an azobenzene core bearing an α,α-difluoromethylphosphonate as a hydrolytically stable phosphate isostere have been prepared with N-Fmoc protection for use in peptide synthesis. Classes of reagents analogous to both phosphotyrosine and phosphoserine/threonine were prepared by a common route employing a nitrosoarene/aniline condensation to form the azo linkage and the Cu(I)-promoted coupling of an iodoarene with (diethylphosphono)difluoromethyl cadmium bromide (Burton's method) to introduce the phosphonate moiety.

CHIRAL ANALYSIS OF THE REACTION STAGES IN THE EDMAN METHOD FOR SEQUENCING PEPTIDES

Chiral isothiocyanate reagents suitable for 'Edman sequencing' have been synthesised and used to assess the chiral features of individual stages in the Edman method.Using h.p.l.c. analysis of the diastereoisomeric thiohydantoins obtained, it has been deduced that the cyclisation and cleavage of thiazolinone step is the likely source of racemisation of the chiral centre derived from the N-terminal amino acid.