21416-43-3

Basic information

• Product Name: S(-)-ALPHA-AMINO-3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINEPROPANOIC ACID
• Synonyms: L-WILLARDIINE;S(-)-ALPHA-AMINO-3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINEPROPANOIC ACID;S(-)-WILLARDIINE;S(-)-WILLARDIINE AMPA/KAINATE AGONIST;willardiine;S(-)-α-Amino--3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinepropanoic acid;(2S)-2-Amino-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidine-1-yl)propionic acid;(S)-2-Amino-3-[2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl]propanoic acid
• CAS NO: 21416-43-3
• Molecular Formula: C₇H₉N₃O₄
• Molecular Weight: 199.16
• Product Categories: Glutamate
• Mol File: 21416-43-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: white/solid
• Density: 1.501 g/cm³
• Refractive Index: 1.543
• Storage Temp.: 2-8°C(protect from light)
• Solubility: 0.1 M NaOH: 7.2 mg/mL
• PKA: 2.12±0.10(Predicted)
• CAS DataBase Reference: S(-)-ALPHA-AMINO-3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINEPROPANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: S(-)-ALPHA-AMINO-3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINEPROPANOIC ACID(21416-43-3)
• EPA Substance Registry System: S(-)-ALPHA-AMINO-3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINEPROPANOIC ACID(21416-43-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 21416-43-3(Hazardous Substances Data)

Usage

Description

S(-)-ALPHA-AMINO-3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINEPROPANOIC ACID, also known as (S)-2-amino-3,4-dihydro-2,4-dioxopyrimidine-3-acetic acid, is a simple amino acid derivative found in germinatine pea seeds or seedlings. Its structure has been determined through chemical and spectroscopic analysis, and it plays a significant role in various biological processes.

Uses

Used in Pharmaceutical Industry:
S(-)-ALPHA-AMINO-3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINEPROPANOIC ACID is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs targeting specific diseases.
Used in Research and Development:
In the field of research and development, S(-)-ALPHA-AMINO-3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINEPROPANOIC ACID serves as an important compound for studying the structure and function of various biological molecules. Its presence in germinatine pea seeds or seedlings makes it a valuable subject for understanding the biochemical processes in plants.
Used in Biochemical Analysis:
S(-)-ALPHA-AMINO-3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINEPROPANOIC ACID is utilized as a reference compound in biochemical analysis. Its unique properties and structure make it a useful tool for comparing and identifying other similar compounds in various biological samples.
Used in Nutritional Supplements:
As a component of germinatine pea seeds or seedlings, S(-)-ALPHA-AMINO-3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINEPROPANOIC ACID may be used as an ingredient in nutritional supplements, particularly those aimed at supporting plant-based diets or enhancing the nutritional value of food products.
Used in Agricultural Industry:
In the agricultural industry, S(-)-ALPHA-AMINO-3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINEPROPANOIC ACID can be employed as a component in the development of genetically modified crops with enhanced nutritional value or improved resistance to diseases and pests. Its presence in germinatine pea seeds or seedlings makes it a potential candidate for crop improvement strategies.

References

Ashworth, Brown, Roberts., Biochern J., 129,897 (1972)

InChI:InChI=1/C7H9N3O4/c8-14-6(12)2-4-10-3-1-5(11)9-7(10)13/h1,3H,2,4,8H2,(H,9,11,13)

Upstream product

• 5147-00-2 O-acetyl-L-serine 
• 66-22-8 uracil 
• 62475-74-5 2-tert-butoxycarbonylamino-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-propionic acid 

Relevant articles and documents

New insight into nucleo α-amino acids – Synthesis and SAR studies on cytotoxic activity of β-pyrimidine alanines

Three series of the β-pyrimidine alanines, including willardiine - a naturally occurring amino acid, were prepared from the L-serine-derived sulfamidates. Compounds 3b, 4a and 4b demonstrated antiproliferative activity toward the studied cancer cell lines, albeit the effect of these compounds on human brain astrocytoma MOG-G-CCM cells was more significant than on human neuroblastoma SK-N-AS cells. The cytosine analog of willardiine, compound 4b, reduced viability of MOG-G-CCM cells with EC50 = 36 ± 2 μM, more effectively than AMPA antagonist GYKI 52466. Willardiine showed possible capability of affecting invasiveness of glioblastoma U251 MG cells with no effect on their viability and morphology. Compound 3d, the ethyl ester of willardiine, featured activity toward binding domain hHS1S2I of the GluR2 receptor. Docking analysis revealed that the location mode of compound 3d at the S1S2 domain of hGluR2 (PDB ID: 3R7X) might differ from that of willardiine.

BIOSYNTHESIS OF β-(1,2,4-TRIAZOL-1-YL)ALANINE IN HIGHER PLANTS

β-(1,2,4-triazol-1-yl)Alanine, an important metabolite of the triazole-based fungicide Myclobutanil, was shown to be derived from O-acetyl-L-serine and 1,2,4-triazole by cysteine synthase in higher plants.Some properties of this enzyme in the biosynthesis of β-(1,2,4-triazol-1-yl)alanine are described.