Asparagin
ASN · ASPARAGINE · H-ASN-OH · L-Asn · Crystal VI · (S)-2,4-Diamino-4-oxobutanoic acid · Asn-OH · L-Asn-OH
Identifikatoren & physikalische Daten
| CAS No. | 70-47-3 |
|---|---|
| Summenformel | C4H8N2O3 |
| Durchschnittliche Molmasse | 132,12 g/mol |
| Monoisotopische Masse | 132,05349212 g/mol |
| SMILES | NC(=O)C[C@H]([NH3+])C(=O)[O-] |
| InChIKey | DCXYFEDJOCDNAF-REOHCLBHSA-N |
| PubChem CID | 6992089 |
| ChEBI | CHEBI:58048 |
| Lokaler Name | Asparagin |
Chemische & physikalische Eigenschaften
| XLogP | -2,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 111 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 128 |
| LogP (Verteilungskoeffizient) | -3.82 |
| Löslichkeit | 29.4 mg/mLPractically insoluble in methanol, ethanol, ether, benzene. Soluble in acids and alkalies.H2O: 20 g/L (20 oC) , clear, colorless |
| Schmelzpunkt | 234-235 °C234 - 235 °C235 °C (dec.) (lit.) |
| Physical Description | Solid |
| Dissociation Constants | 8.82 (at 18 °C) |
| Siedepunkt | 244.01°C (rough estimate) |
| Dichte | 1,543g/cm |
| Brechungsindex | 1.4880 (estimate) |
| Lagerbedingungen | Keep in dark place,Inert atmosphere,Room temperature |
| pKa (Säurekonstante) | 2.17(at 20℃) |
| Aggregatzustand | Powder |
| Farbe | White |
| Geruch | sltly sweet taste |
| pH | 5.41 |
| Merck | 14,837 |
| BRN | 1723527 |
| Henry-Konstante | 9.9×1010 mol/(m3Pa) at 25℃, Saxena and Hildemann (1996) |
| Stabilität | Stable, but may be moisture-sensitive. Incompatible with strong oxidizing agents. |
| Kosmetik-Inhaltsstoffe Funktionen | HAIR CONDITIONINGFRAGRANCEANTISTATICSKIN CONDITIONING |
| InChI | 1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1 |
| InChIKey | DCXYFEDJOCDNAF-REOHCLBHSA-N |
| SMILES | N[C@@H](CC(N)=O)C(O)=O |
| LogP (Verteilungskoeffizient) | -3.820 |
| CAS Datenbank | 70-47-3(CAS DataBase Reference) |
| NIST chemische Informationen | L-Asparagine(70-47-3) |
| EPA chemische Informationen | L-Asparagine (70-47-3) |
Sicherheit & Vorschriften
| F | 3-10 |
|---|---|
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2811 6.1 / PGIII |
| Zollcode | 29241900 |
| R-Sätze (R) | 20/21/22-36/37/38 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 24/25-36-26 |
| Gefahrenklasse | IRRITANT |
| Lagerklasse | 13 - Non Combustible Solids |
| Gefahrstoffdaten | 70-47-3(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Asparagine (abbreviated as Asn or N) is one of the 20 most common natural amino acids on Earth. It has carboxamide as the sidechain's functional group. It is not an essential amino acid. Its codons are AAU and AAC. The amino acid L-asparagine is a structural analog of L-aspartic acid, where the side chain of the carboxylic acid moiety is amidated, to give a terminal amine group. This renders L-asparagine neutral at physiological pH. The amide group of asparagine is derived from glutamate, in the reaction of aspartate and glutamine in the presence of ATP to yield asparagine and glutamate. In vivo, asparagine is hydrolyzed to aspartate and NH4+ by asparaginase. Asparagine is also an important amino acid in glycopeptide bonds, via N-glycosyl linkages to the sugar rings.
Occurrence
Dietary sourcesAsparagine is not essential for humans, which means that it can be synthesized from central metabolic pathway intermediates and is not required in the diet. Asparagine is found in : Animal sources : dairy, whey, beef, poultry, eggs, fish, lactalbumin , sea food Plant sources : asparagus, potatoes, legumes, nuts, seeds, soy, whole grains.BiosynthesisThe precursor to asparagine is oxaloacetate. Oxaloacetate is converted to aspartate using a transaminase enzyme. The enzyme transfers the amino group from glutamate to oxaloacetate producing α- ketoglutarate and aspartate. The enzyme asparagine synthetase produces asparagine, AMP, glutamate, and pyrophosphate from aspartate, glutamine, and ATP. In the asparagine synthetase reaction, ATP is used to activate aspartate, forming β-aspartyl-AMP. Glutamine donates an ammonium group, which reacts with β-aspartyl-AMP to form asparagine and free AMP.
History
Asparagine was first isolated in 1806, under a crystalline form, by French chemists Louis Nicolas Vauquelin and Pierre Jean Robiquet (then a young assistant) from asparagus juice, in which it is abundant — hence, the name they chose for that new matter — becoming the first amino acid to be isolated. A few years later, in 1809, Pierre Jean Robiquet again identified, this time from liquorice root, a substance with properties he qualified as very similar to those of asparagine, that Plisson in 1828 identified as asparagine itself.
Verwenden
L-asparagine has been used:to identify and quantify free amino acids released upon oxidation of proteins and peptides by hydroxyl radicals.to study the effects of amino acids in promoting food consumption in Drosophila melanogaster.to study non-enzymatic gluconeogenesis.L-Asparagine is used in cell culture media and is a component of MEM non-essential amino acids solution.L-Asparagine has been shown to enhance ornithine decarboxylase activity in cultured human colon adenocarcinoma Caco-2 cells and in cultured IEC-6 intestinal epithelial cells. Spore germination in Bacillus subtilis has been increased in the presence of L-asparagine.An isoxazoline RGD mimic platelet GPIIb/IIIa antagonist has been prepared by chiral synthesis with L-asparagine as a starting material. L-Asparagine has been utilized in the synthesis of 4-azalysine building blocks for application to combinatorial chemistry.