36630-89-4

Upstream product

• 20850-34-4 ethyl-(2RS)-2-acetamido-2-cyano-5-phthalimidopentanoate 
• 271601-28-6 1,1-dimethylethyl 4-cyano-(2S)-[(diphenylmethylene)amino]butanoate 
• 50995-48-7 methyl 2,5-dibromovalerate 
• 77300-45-9 2,5-Bis(methoxycarbonylamino)valeriansaeure-methylester 
• 271601-29-7 5-amino-2-(benzhydryl-amino)-pentanoic acid tert-butyl ester 
• 26302-89-6 L-ornithine tert-butyl ester 
• 824956-17-4 tert-butyl 2-amino-4-cyanobutanoate 
• 1119-34-2 L-arginine hydrochloride 
• 88596-94-5 phthalimido-(3-phthalimido-propyl)-malonic acid diethyl ester 

Downstream Products

• 20803-00-3 N⁵-(toluene-4-sulfonyl)-DL-ornithine 
• 60890-27-9 1-(3,4-dimethoxyphenyl)-2-(pyrrolidin-2-yl)ethan-1-one 
• 21079-12-9 N^α-Benzyloxycarbonyl-N^δ-tosyl-DL-ornithin 
• 947401-26-5 Alloc-Orn(Boc)-OH 
• 334618-23-4 3-(R)-aminopiperidine dihydrochloride 
• 92735-06-3 5-Hydroxy-2,2,6,6-tetramethyl-4-pyrrolidin-2-yl-cyclohex-4-ene-1,3-dione 

Relevant academic research and scientific papers

Highly enantioselective synthesis of non-natural aliphatic α-amino acids via asymmetric hydrogenation

By employing a rhodium-Duanphos complex as the catalyst, β-alkyl (Z)-N-acetyldehydroamino esters were smoothly hydrogenated in a highly efficient and enantioselective way. Excellent enantioselectivities together with excellent yields were achieved for a series of substrates. An efficient approach for the synthesis of the intermediate of the orally administered anti-diabetic drugs Alogliptin and Linagliptin in the DPP-4 inhibitor class was also developed.

Synthesis of (ε-13C-,ε-15N)-enriched L-lysine - Establishing schemes for the preparation of all possible 13C and 15N isotopomers of L-lysine, L-ornithine, and L-proline

In this paper we describe a simple synthetic strategy that, with the right rational adaptation, gives direct access to any 13C/15N isotopomer of L-glutamate, L-ornithine, L-proline, L-lysine, and L-α, amino adipic acid. This strategy also allows access to nonproteinogenic amino acids like L-citrulline in high yields and optical purity. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

9-BBN: An amino acid protecting group for functionalization of amino acid side chains in organic solvents.

9-Borabicyclononane (9-BBN) has been utilized to protect functionalized amino acids for potential chemoselective side chain manipulation. The 9-BBN group imparts organic solubility to otherwise hydrophilic molecules and is tolerant of a wide range of reaction conditions. The high degree of solubility of these molecules in THF is particularly noteworthy. It is cleaved with either aqueous HCl or by exchange with ethylenediamine in methanol. [reaction: see text]

Highly enantioselective Michael reactions catalyzed by a chiral quaternary ammonium salt. Illustration by asymmetric syntheses of (S)-ornithine and chiral 2-cyclohexenones.

[formula: see text] The use of the chiral quaternary ammonium salts 1a and 1b makes possible enantioselective Michael reactions which have been applied to the asymmetric syntheses of (S)-ornithine (2) and the chiral 2-cyclohexenone 6.

Polyunsaturated fatty acid derivatives, pharmaceutical compositions containing the same, method for the preparation thereof, and their use as medicament

The compounds of the Formula (I) STR1 wherein R1 is a C18-24 alkenyl containing at least two double bonds, or --(CH2)n --CH(NH2)m --COOH X is 0, NH or C1-4 alkyl-N, Y is CONH2, COOH or COOMe, wherein Me is hydrogen metal, and R2 is a side chain of a any amino acid except L-GLU or L-ASP at α-position or a group of Formula wherein k is zero or an integer of 1, n is zero or an integer of 1 to 3, m is zero or an integer of 1 to 4, A is hydroxyl or one A is hydroxyl and the other A is hydrogen. M is H or R1 --CO and X and R1 are as defined above and their salts having tyrosine kinase inhibitor activity can be used as antitumor agents.

Thermochemistry of the hydrolysis of L-arginine to (L-citrulline + ammonia) and of the hydrolysis of L-arginine to (L-ornithine + urea)

Molar enthalpies of reaction for the hydrolysis of L-arginine(aq) to and for the hydrolysis of L-arginine(aq) to have been measured by microcalorimetry.These reactions are catalyzed, respectively, by arginase and by arginine deiminase.The effects of variations in pH, temperature, and ionic strength on the molar enthalpies of reaction were studied.The results have been analyzed with a model which accounts for the complex equilibria in solution.The results obtained at T = 298.15 K for the reference reactions are: ΔfHm0 = -(21.4+/-0.5) kJ * mol-1 for L-arginine+(aq) + H2O(l) = L-ornithine+(aq) + urea(aq) and ΔfHm0 = -(31.9+/-0.8) kJ * mol-1 for L-arginine+(aq) + H2O(l) = L-citrulline(aq) + NH4+(aq).These results are discussed in terms of thermodynamic-cycle calculations and in terms of the metabolic urea cycle.

Biosynthesis of blasticidin S from L-α-arginine. Stereochemistry in the arginine-2,3-aminomutase reaction

A series of labeled α-arginines have been fed to fermentations of Streptomyces griseochromogenes in order to examine the mechanism of L-β-arginine formation in the biosynthesis of the antibiotic blasticidin S. [3-13C,2-15N]Arginine was synthesized and fed; analysis of the derived antibiotic by 13C NMR spectroscopy revealed the retention of the original α-nitrogen and its intramolecular migration to the β-position, revealing the presence of an arginine-2,3-aminomutase. Feedings of [2,3,3-2H3]-, [3,3-2H2]-, and [2-2H]arginines revealed the complete retention of the original β-hydrogens with migration of one to the α-position, as well as partial loss of the original α-hydrogen presumably due to arginine racemase activity. (3R)-[3-2H]- and (3S)-[3-2H]arginines were synthesized unambiguously and used to determine that the pro-3R hydrogen of α-arginine migrates to the α-position (C-2). δ-N-[13CH3]Methylarginine was synthesized, mixed with [guanidino-14C]arginine, and fed to S. griseochromogenes. A 42% incorporation of radioactivity from arginine was obtained, but no 13C enrichment was observed in the blasticidin S sample, indicating that arginine, itself, is the aminomutase substrate.

The biosynthesis of the streptolidine moiety in streptothricin F

A series of arginines specifically labeled either with 13C and 15N or with 2H were synthesized and fed to Streptomyces L-1689-23. The streptothricin F isolated in each case was analyzed by either 13C or 2H NMR, respectively, in order to determine the labeling pattern obtained. From these results, it appears that arginine is metabolized to a β-ketoarginine, possibly via a pyridoxal phosphate adduct, and then via cyclization, reduction, rearrangement, and hydroxylation to the streptolidine moiety. The pathway described can also account for the formation of other known antibiotics, and for β-hydroxy-γ-amino acids, generally.

Aminosaeuren, I. Darstellung von Aminosaeuren aus Halogencarbonsaeure-alkylestern mit Alkalimetallcyanaten

α- and ω-halo- as well as α,ω-dihalocarboxylic alkyl esters react with potassium cyanate in the presence of alcohol at 80 - 120 deg C in dipolar aprotic solvents to yield α- and ω-(alkoxycarbonylamino)- and α,ω-bis(alkoxycarbonylamino)carboxylic alkyl esters, respectively, in good yields.Hydrolytic cleavage of these mono- or diurethanes with an aqueous solution of hydrochloric acid/formic acid leads to the corresponding amino acid hydrochlorides in nearly quantitative yields.

Process for the production of aminoacid hydrochlorides/or diaminoacid dihydrochlorides

Aminoacid hydrochlorides or diaminoacid dihydrochlorides are produced by first reacting a halocarboxylic acid ester with an alkali metal cyanate in the presence of an alcohol to form the corresponding mono- or diurethane and then saponifying this to the corresponding mono- or dihydrochloride. The new process is relatively versatile in its use and above all opens up an elegant synthesis route for lysine.