462-88-4

Usage

Uses

Used in Pharmaceutical Industry:
3-UREIDOPROPIONIC ACID is used as an intermediate in the synthesis of various pharmaceutical compounds for its role in linking uracil to β-Alanine metabolism. This makes it a valuable component in the development of drugs targeting metabolic disorders and other related conditions.
Used in Biochemical Research:
3-UREIDOPROPIONIC ACID is used as a research tool in biochemical studies for its involvement in uracil and β-Alanine metabolism. It aids scientists in understanding the underlying mechanisms of these metabolic pathways and contributes to the advancement of knowledge in the field of biochemistry.
Used in Nutritional Supplements:
3-UREIDOPROPIONIC ACID is used as a nutritional supplement to support the synthesis of uracil and β-Alanine, which are essential for various physiological processes in the body. It can be incorporated into dietary supplements to promote overall health and well-being.

InChI:InChI=1/C4H8N2O3/c5-4(9)6-2-1-3(7)8/h1-2H2,(H,7,8)(H3,5,6,9)/p-1

Upstream product

• 504-07-4 5,6-dhydrouracil 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 18019-23-3 N-carbamoyl-β-alanine methyl ester 
• 84-53-7 uridine-3'-phosphate 
• 131-83-9 uridine 2'-monophosphate 
• 590-28-3 potassium cyanate 
• 107-95-9 3-amino propanoic acid 

Downstream Products

• 504-07-4 5,6-dhydrouracil 
• 1350618-25-5 methyl 3-(4,6-diethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)propanoate 
• 134-81-6 benzil 
• 105-55-5 N,N'-diethylthiourea 
• 1350618-21-1 methyl 3-(4,6-dimethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)propanoate 
• 123351-54-2 4,5-dimethoxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione 
• 534-13-4 N,N-dimethylthiourea 
• 1350618-34-6 1,3-diethyl-5,5-diphenyl-2-thioxoimidazolidin-4-one 
• 1350618-31-3 isopropyl 3-(4,6-diethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)propanoate 
• 1350618-27-7 isopropyl 3-(4,6-dimethyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)propanoate 
• 1188-38-1 L-carglumic acid 
• 949237-99-4 3-[5-(ethoxycarbonyl)-6-methyl-2-oxo-4-phenyl-3,4-dihydropyrimidin-1(2H)-yl]propanoic acid 
• 1266096-34-7 C₂₄H₂₈N₄O₄ 
• 107-95-9 3-amino propanoic acid 

Relevant academic research and scientific papers

Synthesis of 2-monofunctionalized 2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7- diones

New (1R*,5S*)-2-R-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7- diones containing the terminal carboxy or hydroxy group in the substituent R were synthesized by cyclocondensation of 4,5-dihydroxyimidazolidin-2-one with 1-R-ureas. Single-crystal X-ray diffraction analysis showed that 2-carboxyethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione crystallizes as a racemate.

New functional glycoluril derivatives

Functional glycoluril (2,4,6,8-tetraazabicyclo[3.3.0]octan-3,7-dione) derivatives containing 2-hydroxyethyl, carboxyl and amino groups were synthesised.

A pH-dependent cyanate reactivity model: Application to preparative N-carbamoylation of amino acids

Recent developments in peptide synthesis have underlined the importance of optimising, on a preparative scale, the N-carbamoylation of amino acids by aqueous cyanate. To this purpose, a theoretical model of aqueous cyanate reactivity was designed. The parameters of the model were evaluated, for various pH and temperatures, from a critical survey of the literature, together with additional experimental data. Computer-simulated kinetics based on this model showed the reaction efficiency to be significantly dependent on pH, and suggested optimum conditions to be moderate temperatures and pH 8.5-9. Discussion of the practical convenience of these theoretical results led us to prefer 40-50 °C and a pH range of 7-8 as reaction conditions, thus maintaining reaction times within a few hours. Various N-carbamoyl amino acids (ureido derivatives of glycine, L-valine, L-alanine, L-leucine, DL-methionine, Nε-trifluoroacetyl-L-lysine, β-alanine) were thus successfully synthesised on the gram to kilogram scales.

Mechanism of Asymmetric Production of D-Amino Acids from the Corresponding Hydantoins by Pseudomonas sp.

The mechanism of asymmetric production of D-amino acids from the corresponding hydantoins by Pseudomonas sp.AJ-11220 was examined by investigating the properties of the enzymes involved in the hydrolysis of DL-5-substituted hydantoins.The enzymatic production of D-amino acids from the corresponding hydantoins by Pseudomonas sp.AJ-11220 involved the following two successive reactions; the D-isomer specific hydrolysis, i.e., the ring opening of D-5-substituted hydantoins to D-form N-carbamyl amino acids by an enzyme, D-hydantoin hydrolase (D-HYD hydrolase), followed by the D-isomer specific hydrolysis, i.e., the cleavage of N-carbamyl-D-amino acids to D-amino acids by an enzyme, N-carbamyl-D-amino acid hydrolase (D-NCA hydrolase).L-5-Substituted hydantoins not hydrolyzed by D-HYD hydrolase were converted to D-form 5-substituted hydantoins through spontaneous racemization under the enzymatic reaction conditions.It was proposed that almost all of the DL-5-substituted hydantoins were stoichiometrically and directly converted to the corresponding D-amino acids through the successive reactions of D-HYD hydrolase and D-NCA hydrolase in parallel with the spontaneous racemization of L-5-substituted hydantoins to those of DL-form.

β-UREIDO ACIDS AND DIHYDROURACILS. PART 15. EFFECT OF ALLYLIC STRAIN ON RING OPENING OF 1,6-DISUBSTITUTED DIHYDROURACILS

The rate profiles for the alkaline hydrolysis of some dihydrouracil and dihydro-orotic acid derivetives have been measured in order to assess the effect of allylic strain on the ring opening of 1,6-disubstituted dihydrouracils.The introduction of a 1-nitrogen-substituent in the 6-substituted compounds brings about a substantial decrease (40-500 times) in the observed rate constant which is second order in hydroxide ion (k1k3/k-1).The rate decreases of the addition step, k1, are moderate and in the range expected from the observed shifts in conformational equilibra towards the axial conformation which gives rise to a hindered transition state.The major contribution to the rate decreases from the ring-opening step, k3/k-1, and have been attributed to strains of the type associated with gem-dimethyl effect upon ring closure.