1655-52-3

Usage

Uses

Used in Biochemical Research:
N-(2,4-Dinitrophenyl)-L-alanine is used as a reagent for detecting and quantifying amino acids in biological samples. The dinitrophenyl group's reaction with the amino group of the amino acid forms a colored product that can be easily measured and identified, aiding in the study of protein structure, function, and metabolism.
Used in Clinical Chemistry:
In the field of clinical chemistry, N-(2,4-Dinitrophenyl)-L-alanine is utilized for diagnosing and monitoring medical conditions related to amino acid metabolism. Its application helps in understanding and managing conditions that affect the body's amino acid balance and processing.

InChI:InChI=1/C9H9N3O6/c1-5(9(13)14)10-7-3-2-6(11(15)16)4-8(7)12(17)18/h2-5,10H,1H3,(H,13,14)/t5-/m0/s1

Upstream product

• 56-41-7 L-alanin 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 610-31-1 1,2,4-trinitrobenzene 
• 99-65-0 meta-dinitrobenzene 
• 302-72-7 rac-Ala-OH 
• 83093-94-1 methyl 6,7-dideoxy-6-(2,4-dinitrophenyl)amino-L-glycero-D-gluco-heptopyranoside 
• 584-48-5 2,4-dinitrobromobenzene 
• 52-90-4 L-Cysteine 

Downstream Products

• 10420-63-0 (S)-methyl 2-((2,4-dinitrophenyl)amino)propanoate 
• 51-28-5 2,4-Dinitrophenol 
• 4615-69-4 2-methyl-5-nitro-1H-benzimidazole-3-oxide 
• 223271-83-8 (S)-2-{(S)-2-[(S)-2-(2,4-Dinitro-phenylamino)-propionylamino]-3-hydroxy-propionylamino}-3-phenyl-propionic acid methyl ester 
• 15159-79-2 C₉H₈ClN₃O₅ 

Relevant academic research and scientific papers

Iron- or Zinc-Mediated Synthetic Approach to Enantiopure Dihydroquinoxalinones

A general and efficient synthesis of enantiopure dihydroquinoxalinones has been developed using naturally occurring amino acids as starting materials. The reductive cyclization of N-(o-nitroaryl)amino esters was performed by using iron and zinc metal under mild conditions in a water/ethyl acetate mixture. The corresponding dihydroquinoxalinones were obtained in moderate to high yields and high enantiomeric purity, among which 7 new compounds were unprecedented in the literature.

Simple and efficient preparation of (R)- and (S)-enantiomers of α-carbon deuterium-labelled α-amino acids

A procedure for the synthesis of (R)- and (S)-enantiomers of α-carbon deuterium-labelled α-amino acids, exemplified for (R)- and (S)-[2-2H1]-Leu is described. Starting from the respective (S)- or (R)-enantiomer or from the racemic mixture of an α-amino acid the selective proton exchange at the α-carbon is carried out by racemization via a Schiff base in monodeuterated acetic acid as solvent which serves as deuterium source. After N-protection the racemic mixture is liquid chromatographically separated into the individual (R)- and (S)-enantiomers on preparative scale employing a chiral anion exchanger based on carbamoylated quinine as chiral selector. After deprotection the enantiomerically pure products can be obtained in good yields.

Efficient nucleophilic substitution reaction of aryl halides with amino acids under focused microwave irradiation

The nucleophilic substitution reaction of 2,4-dinitrofluorobenzene with amino acids was complete, under microwave iradiation, within 40 s with yields up to 93%, which are far superior to those obtained under conventional heating. (C) 2000 Elsevier Science Ltd.

Synthesis of new chromogenic substrates for aspartyl proteases

A general method was developed for the synthesis of new chromogenic substrates of aspartyl proteases: Dnp-Ala-Xaa-Phe-Phe-Ala-Arg-NH2, where Xaa was Ala or Ser. The synthetic scheme involved both chemical and enzymic stages, the condensation of tripeptides in an organic medium by means of pepsin immobilized on Celite being among the latters. The influence of organic solvents, reaction time, and the composition and ionic strength of the buffers used in the reaction mixture and at the pepsin immobilization step on the efficacy of the pepsin-catalyzed synthesis was studied.

1,2,4-TRINITROBENZENE AS A THIOL REAGENT

The 2,4-dinitrophenylation of thiol or amino group with 1,2,4-trinitrobenzene proceeded quantitatively at pH 8.5 and 30 deg C.The rate of S-dinitrophenylation was ca. 1E4 times faster than that of N-dinitrophenylation.So this reaction can be used for both the determination of thiol even in the presence of large excess amine and the specific modification of thiol in proteins.

SYNTHESIS OF DESTOMIC AND epi-DESTOMIC ACID, AND THEIR C-6 EPIMERS

Four stereoisomers of 6-amino-6-deoxyheptonic acid, having the L-glycero-D-galacto (1), D-glycero-D-galacto (2), L-glycero-D-gluco (3), and D-glycero-D-gluco(4) configurations, were synthesized from D-galacto- (8) and D-gluco-dialdose (23) derivatives, respectively.Cyanomesylation of 8 and 23 gave two C-6 epimers, respectively, which were separately converted, via the corresponding 6,7-epimino derivatives, into 6-(benzyloxycarbonyl)amino-6-deoxy derivatives by reduction with lithium aluminium hydride, N-(benzyloxycarbonyl)ation, and acetolysis with acetic acid.After deprotection of each hemiacetal, the stereoisomers were oxidized with bromine, followed by total deprotection, to give 1-4.Among these products, 1 and 3 proved to be identical with the naturally occuring destomic and epi-destomic acid obtained from antibiotic destomycins.