35068-04-3

Upstream product

• 108-24-7 acetic anhydride 
• 3417-91-2 L-tyrosine methyl ester HCl 
• 60470-84-0 methyl (Z)-2-acetamido-3-(4-acetoxyphenyl)acrylate 
• 1080-06-4 L-Tyr-OMe 
• 15852-46-7 N-acetyl-L-phenylalanyl-L-tyrosine methyl ester 
• 60-18-4 L-tyrosine 
• 82911-79-3 N-(fluorenyl-9-methoxycarbonyl)-L-tyrosine methyl ester 

Downstream Products

• 7423-96-3 3-fluoro-DL-tyrosine 
• 78709-81-6 2-fluoro-L-tyrosine 
• 2440-79-1 N-acetyl-L-tyrosine methyl ester 
• 1309350-26-2 3-(4-acetoxy-3-nitrophenyl)-2-(N-nitrosoacetamido)propionic acid methyl ester 
• 60521-90-6 3-(4-acetoxy-3-nitrophenyl)-2-acetylaminopropionic acid methyl ester 

Relevant academic research and scientific papers

Oxidative damage of aromatic dipeptides by the environmental oxidants NO2 and O3

Irreversible oxidative damage at both aromatic side chains and dipeptide linkage occurs in the aromatic N- and C-protected dipeptides 7-11 upon exposure to the environmental pollutants NO2 and O3. The reaction proceeds through initial oxidation of the aromatic ring by in situ generated NO3, or by NO2, respectively, which leads to formation of nitroaromatic products. The indole ring in Phe-Trp undergoes oxidative cyclization to a pyrroloindoline. An important reaction pathway for dipeptides with less oxidisable aromatic side chains proceeds through fragmentation of the peptide bond with concomitant acyl migration. This process is likely initiated by an ionic reaction of the amide nitrogen with the NO2 dimer, N2O4. This journal is

Alternative and chemoselective deprotection of the α-amino and carboxy functions of N-Fmoc-amino acid and N-Fmoc-dipeptide methyl esters by modulation of the molar ratio in the AlCl3/N,N-dimethylaniline reagent system

The amino and carboxy functions in N-Fmoc-α-amino acid and N-Fmoc-peptide methyl esters can be alternatively and chemoselectively deprotected by treatment with the reagent system AlCl3/N,N- dimethylaniline (DMA). The chemoselectivity of the process is controlled by modulating the relative molar ratio of the Lewis acid and DMA. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Differentiation of natural and synthetic phenylalanine and tyrosine through natural abundance 2H nuclear magnetic resonance

The natural abundance deuterium NMR characterization of samples of the amino acids tyrosine (1) and phenylalanine (2), examined as the acetylated methyl esters 4 and 6, has been performed with the aim to identify by these means the contribution in animals of the hydroxylation of the diet L-phenylalanine (2) to the formation of L-tyrosine (1), a feature previously revealed on the same samples through the determination of the phenolic δ18O values. The study, which includes also the NMR examination of benzoic acid (5) from 2 and of tyrosol (7) from 1, substantially fails in providing the required information because the mode of deuterium labeling of tyrosine samples of different origins is quite similar but indicates a dramatic difference in the deuterium labeling pattern of the two amino acids 1 and 2. The most relevant variation is with regard to the deuterium enrichments at the CH2 and CH positions, which are inverted in the two amino acids of natural derivation. Moreover, whereas the diastereotopic benzylic hydrogen atoms of L-tyrosine (1) appear to be equally deuterium enriched, in L-phenylalanine (2) the (D/H)3R > (D/H)3S. Similarly, benzoic acid (5) shows separate signals for the aromatic deuterium nuclei, which are quite indicative of the natural or synthetic derivation. The mode of deuterium labeling of the side chain of 1 and 2 is tentatively correlated to the different origins of the two amino acids, natural from animal sources for L-tyrosine and biotechnological probably from genetically modified microorganisms for L-phenylalanine.

Rhodium-catalyzed asymmetric hydrogenation with aminophosphine ligands derived from 1,1′-binaphthyl-2,2′-diamine

Chiral ligands 2,2′-bis(dicyclohexylphosphinoamino)-1,1′-binaphthyl and 2,2′-bis[bis(3,5-dimethylphenyl)phosphinoamino]-1,1′-binaphthyl were synthesized by reacting 1,1′-binaphthyl-2,2′-diamine with dicyclohexylchlorophosphine and bis(3,5-dimethylphenyl)chlorophosphine, respectively. Application of these ligands to the Rh-catalyzed asymmetric hydrogenation of a variety of amidoacrylic acids and esters provided chiral amino acid derivatives with excellent enantioselectivities (up to 99% e.e. and quantitative yields).

Modified BINAPO ligands for Rh-catalysed enantioselective hydrogenation of acetamidoacrylic acids and esters

(S)- and (R)-2,2′-Bis[bis(3,5-dimethylphenyl)phosphinoyl]-5,5′,6, 6′,7,7′,8,8′-octahydro-1,1′-binaphthyl (Xyl-H8-BINAPO) were synthesised by reacting chlorobis(3,5-dimethylphenyl)phosphine with (S)- and (R)-2,2′-dihydroxyl-5,5′,6,6′,7,7′,8,8′-

Asymmetric hydrogenation of dehydroamino acid derivatives catalyzed by a new aminophosphine phosphinite ligand derived from ketopinic acid

A new chiral aminophosphine phosphinite N,O-bis(diphenylphosphino)-(1S,2R)-1-(N-methylamino) methyl-2-hydroxyl-7,7-dimethylbicyclo[2.2.1]heptane was synthesized from ketopinic acid and its application to the asymmetric hydrogenation of dehydroamino acid d

Asymmetric synthesis XXVIII: Novel chiral aminophosphine phosphinite ligand and its application in homogeneous catalytic asymmetric hydrogenation of dehydroamino acid derivatives

Novel chiral aminophosphine phosphinite, DPAMPP was designed and synthesized from (1S,2R)-1,2-diphenyl-2-aminoethanol. Its cationic rhodium complex has been found to be an excellent catalyst for enantioselective hydrogenation of dehydroamino acids (more t

SYHTHESIS OF 2- AND 3-FLUOROTYROSINE WITH DILUTE FLUORINE GAS

Differences in reactivity and selectivity of fluorine gas towards L-tyrosine and the O,N-diacetylated derivative of L-tyrosine methyl ester have been exploited for the synthesis of 2- and 3-fluorotyrosine.Both 2- and 3-fluorotyrosine were identified by 2H, 19F and 13C NMR spectroscopy and high resolution mass spectrometry.The short synthesis time and high reaction yields allow this procedure to be used for the incorporation of the short lived positron emitting radionuclide 18F into the aromatic ring of L-tyrosine.