L-베타-아스파라긴
L-베타-아스파라긴 · L-아스파라긴 · ASN · ASPARAGINE · H-ASN-OH · L-Asn · Crystal VI · (S)-2,4-Diamino-4-oxobutanoic acid
식별자 및 물리적 특성
| CAS No. | 70-47-3 |
|---|---|
| 분자식 | C4H8N2O3 |
| 평균 분자량 | 132.12 g/mol |
| 단동위원소 질량 | 132.05349212 g/mol |
| SMILES | NC(=O)C[C@H]([NH3+])C(=O)[O-] |
| InChIKey | DCXYFEDJOCDNAF-REOHCLBHSA-N |
| PubChem CID | 6992089 |
| ChEBI | CHEBI:58048 |
| 현지명 | L-베타-아스파라긴 |
화학 및 물리적 성질
| XLogP | -2.8 |
|---|---|
| 극성 표면적 | 111 |
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 9 |
| 형식 전하 | 0 |
| 복잡도 | 128 |
| LogP(분배 계수) | -3.82 |
| 용해도 | 29.4 mg/mL메탄올, 에탄올, 에테르, 벤젠에는 거의 녹지 않습니다. 산과 알칼리에 용해됩니다. |
| 녹는점 | 234-235 °C234 - 235 °C235 °C (dec.) (lit.) |
| Physical Description | Solid |
| Dissociation Constants | 8.82 (at 18 °C) |
| 끓는 점 | 244.01°C (rough estimate) |
| 밀도 | 1,543g/cm |
| 굴절률 | 1.4880 (estimate) |
| 저장 조건 | Keep in dark place,Inert atmosphere,Room temperature |
| pKa(산도 계수) | 2.17(at 20℃) |
| 물리적 상태 | 가루 |
| 색상 | 하얀색 |
| 냄새 | 살짝 달콤한 맛 |
| pH | 5.41 |
| 용해도 | H2O: 20 g/L (20 oC) , 투명, 무색 |
| Merck | 14,837 |
| BRN | 1723527 |
| 헨리 상수 | 9.9×1010 mol/(m3Pa) at 25℃, Saxena and Hildemann (1996) |
| 안정성 | 안정적이지만 습기에 민감할 수 있습니다. 강한 산화제와 호환되지 않습니다. |
| 화장품 원료 기능 | 헤어 컨디셔닝향기대전방지제피부 컨디셔닝 |
| 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(분배 계수) | -3.820 |
| NIST | L-Asparagine(70-47-3) |
| EPA | L-Asparagine (70-47-3) |
화학적 성질
White crystal or crystalline powder with a slightly sweet taste. Slightly soluble in water, insoluble in ethanol and ether, it often exists as a monohydrate, and it is a rhombic hemihedral crystals. The melting point is 234-235°C , and the aminocarbonyl reaction is carried out by co-heating with sugar, which can form special aroma substances. The best recrystallization method is water, followed by ethanol. In case of alkali hydrolysis into aspartic acid. Heating its aqueous solution also decomposes. Natural products exist in various legumes and the like.
안전 및 규제
| 수질 위해 등급(WGK) | 3 |
|---|---|
| TSCA 등재 상태 | TSCA listed |
| 운송 번호(UN) | UN 2811 6.1 / PGIII |
| 관세 코드 | 29241900 |
| 위험 문구(R) | 20/21/22-36/37/38 |
| 위험 표시 | Xn |
| 안전 문구(S) | 24/25-36-26 |
| 위험 등급 | IRRITANT |
| 기존화학 물질 | KE-01953 |
| F 고인화성물질 | 3-10 |
| 저장 분류 | 13 - Non Combustible Solids |
| 유해 물질 데이터 | 70-47-3(Hazardous Substances Data) |
용도
개요
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.
출처
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.
역사
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.
용도
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.
제조 및 합성 방법
생산 방법
A simple synthesis of L -asparagine starts from L -aspartic acid which is esterified to the b-methyl ester followed by treatment with ammonia.