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| 融点 | 185 °C (dec.) (lit.) | | 沸点 | 265.74°C (rough estimate) | | 比旋光度 | 32.25 º (c=10, 2 N HCl) | | 比重(密度) | 1.47 g/cm3 (20℃) | | FEMA | 3684 | L-GLUTAMINE | | 屈折率 | 6.8 ° (C=4, H2O) | | 闪点 | 185°C | | 貯蔵温度 | Store below +30°C. | | 溶解性 | H2O: 25 mg/mL | | 外見 | solution | | 酸解離定数(Pka) | 2.17(at 25℃) | | 色 | White | | PH | 5.0-6.0 (25℃, 0.1M in H2O) | | 臭い (Odor) | at 100.00 %. very mild milky custard cocoa oily | | においのタイプ | milky | | 光学活性 (optical activity) | [α]20/D +33.0±1°, c = 5% in 5 M HCl | | 水溶解度 | Soluble in water, dimethyl sulfoxide and ethanol. Insoluble in methanol, ether, benzene, acetone, ethyl acetate and chloroform. | | Decomposition | 185 ºC | | 極大吸収波長 (λmax) | λ: 260 nm Amax: 0.01
λ: 280 nm Amax: 0.01 | | JECFA Number | 1430 | | Merck | 14,4471 | | BRN | 1723797 | | 安定性： | Moisture and light sensitive. Incompatible with moisture, strong oxidizing agents. | | InChIKey | ZDXPYRJPNDTMRX-VKHMYHEASA-N | | LogP | -1.67 | | CAS データベース | 56-85-9(CAS DataBase Reference) | | NISTの化学物質情報 | L-Glutamine(56-85-9) | | EPAの化学物質情報 | L-Glutamine (56-85-9) |
| | L-グルタミン Usage And Synthesis |
| 外観 | 白色, 結晶～粉末 | | 定義 | グルタミン酸のγ(ガンマ)-アミドで、栄養的には非必須(ひひっす)アミノ酸。略号はGlnまたはQ。化学式はC5H10N2O3で、分子量146.15。1883年ドイツの化学者シュルツェErnst August Schulze（1840―1912）とボシャードE. Bosshardがテンサイ汁の中から発見した。遊離状態で多くの動植物中に分布する。L-グルタミンはタンパク質を構成するアミノ酸の一つで、生体内ではアンモニア貯蔵の役割を果たし、核酸のプリン核の生成などに関与する。また、フェニル酢酸と結合して解毒する。腎臓(じんぞう)その他の組織中で、グルタミン酸とアンモニアから合成される。［降旗千恵］ | | 定義 | 本品は、次の化学式で表されるアミノ酸である。 | | 溶解性 | 水100gに4.25g (25℃)溶解。エタノール, エーテルに殆ど不溶。水にやや溶けやすく、エタノール及びジエチルエーテルにほとんど溶けない。 | | 解説 | 2-aminoglutaramic acid．C5H10N2O3(146.15)．H2NCO-CH2CH2CH(NH2)COOH．略記号Gln．アミド基をもつα-アミノ酸．タンパク質中，または遊離の状態で広く分布している．甜(てん)菜汁から水銀塩として分離する．グルタミン酸からγ-モノエステルを経て合成することができる．水溶液を加熱するとピロリドンカルボン酸になる．アルカリ性にして加熱すると，グルタミン酸とアンモニアに分解する．L-グルタミンは微針状結晶(水)．融点185～186 ℃(分解)．[α]23D＋6.1°(水)．pK1 2.17，pK2 9.13．pI5.65．医薬品として用いられる．[CAS 56-85-9]
森北出版「化学辞典（第2版） | | 用途 | アンモニアと結合して、アン モニア低下作用を示します。 | | 用途 | アンモニアと結合して、アン
モニア低下作用を示します。 | | 用途 | アミノ酸研究用、医薬原料。 | | 栄養成分としての働き | グルタミンは骨格筋に貯蔵されているアミノ酸の約6割を占め、体内でたんぱく質が分解されるのを抑え、筋肉の維持に重要な役目をはたしています。また細胞の柔軟性を維持します。この働きがスポーツ選手に最適なのはもちろんですが、手術後で体を動かせない患者さんが、できるだけ筋肉を失わず体力を保持できるよう、医療現場でも点滴に添加されることがあります。グルタミンは、窒素代謝(ちっそたいしゃ)に関与し、たんぱく質や核酸などの前駆物質にもなります。またインスリンの分泌(ぶんぴつ)を刺激せずにグルコースに変換され、腸の細胞やリンパ球など、短時間で分裂する細胞のエネルギー源となります。インスリンは体内での脂肪の沈着に作用するので、体脂肪を抑えるのにグルタミンが効果を発揮するわけです。さらに免疫機能の向上にも作用すると考えられています。グルタミンは肉や魚、たまごなどに比較的多く含まれていますが、加熱により変性するので、食事からの摂取はむずかしく、サプリメントが有効です。 | | 化粧品の成分用途 | ヘアコンディショニング剤、皮膚コンディショニング剤 | | 効能 | 消化性潰瘍薬, 栄養補助食品 | | 確認試験 | 本品につき，赤外吸収スペクトル測定法〈2.25〉の
臭化カリウム錠剤法により試験を行い，本品のスペクトルと
本品の参照スペクトルを比較するとき，両者のスペクトルは
同一波数のところに同様の強度の吸収を認める． | | 定量法 | 本品を乾燥し，その約0.15gを精密に量り，ギ酸3mL
に溶かし，酢酸(100)50mLを加え，0.1mol/L過塩素酸で滴
定〈2.50〉する(電位差滴定法)．同様の方法で空試験を行い，
補正する．
0.1mol/L過塩素酸1mL＝14.61mg C5H10N2O3 | | 純度試験 | (１) 溶状 本品0.5gを水20mLに溶かすとき，液は無色澄
明である．
(２) 塩化物〈1.03〉 本品0.5gをとり，試験を行う．比較
液には0.01mol/L塩酸0.30mLを加える(0.021％以下)．
(３) 硫酸塩〈1.14〉 本品0.6gをとり，試験を行う．比較
液には0.005mol/L硫酸0.35mLを加える(0.028％以下)．
(４) アンモニウム〈1.02〉 本品0.10gをとり，試験を行う．
比較液にはアンモニウム標準液10.0mLを用いる(0.1％以下)．
ただし，本試験は減圧蒸留法により行い，水浴の温度は
45℃とする．
(５) 重金属〈1.07〉 本品1.0gをとり，第1法により操作し，
試験を行う．比較液には鉛標準液1.0mLを加える(10ppm以
下)．
(６) 鉄〈1.10〉 本品1.0gをとり，第1法により検液を調製
し，A法により試験を行う．比較液には鉄標準液1.0mLを加
える(10ppm以下)．
(７) 類縁物質 本品0.10gを水10mLに溶かし，試料溶液
とする．この液1mLを正確に量り，水を加えて正確に10mL
とする．この液1mLを正確に量り，水を加えて正確に50mL
とし，標準溶液とする．これらの液につき，薄層クロマトグ
ラフィー〈2.03〉により試験を行う．試料溶液及び標準溶液
5μLずつを薄層クロマトグラフィー用シリカゲルを用いて調
製した薄層板にスポットする．次に1－ブタノール／水／酢
酸(100)混液(3：1：1)を展開溶媒として約10cm展開した後，
薄層板を80℃で30分間乾燥する．これにニンヒドリンのメ
タノール／酢酸(100)混液(97：3)溶液(1→100)を均等に噴霧
した後，80℃で10分間加熱するとき，試料溶液から得た主
スポット以外のスポットは，標準溶液から得たスポットより
濃くない． | | 貯法 | 容器 気密容器． | | 乾燥減量 | 0.3％以下(1g，105℃，3時間)． | | 強熱残分 | 0.1％以下(1g)． | | 説明 | Glutamine (abbreviated as Gln or Q) is one of the 20 amino acids encoded by the standard genetic code. It is not recognized as an essential amino acid, but may become conditionally essential in certain situations, including intensive athletic training or certain gastrointestinal disorders.Its side-chain is an amide formed by replacing the side-chain hydroxyl of glutamic acid with an amine functional group, making it the amide of glutamic acid. Its codons are CAA and CAG. In human blood, glutamine is the most abundant free amino acid, with a concentration of about 500–900 μmol / l . | | 化学的特性 | White, odorless crystals or crystalline powder having a slightly
sweet taste. It is soluble in water and practically insoluble in
alcohol and in ether. Its solutions are acid to litmus. It melts with
decomposition at about 185°C. | | 化学的特性 | White crystalline powder | | 化学的特性 | L-glutamine is odorless, but has a slightly sweet taste L-glutamine performs a major role in DNA synthesis and sup- ports the immune system by means of glutathione synthesis. | | 天然物の起源 | Occurrences in nature
Glutamine is the most abundant naturally occurring, nonessential amino acid in the human body, and one of the few amino acids that can directly cross the blood-brain barrier.In the body, it is found circulating in the blood, as well as stored in the skeletal muscles. It becomes conditionally essential (requiring intake from food or supplements) in states of illness or injury.Dietary sources
Dietary sources of L-glutamine include beef, chicken, fish, eggs, milk, dairy products, wheat, cabbage, beets, beans, spinach, and parsley. Small amounts of free L-glutamine are also found in vegetable juices.
Aiding gastrointestinal functionGlutamine-enriched diets have been linked with maintenance of gut barrier function and cell differentiation, suggesting glutamine may help to protect the lining of the gastrointestinal tract or mucosa. People who have inflammatory bowel disease (ulcerative colitis and Crohn' s disease) may not have enough glutamine, but two clinical trials found taking glutamine supplements did not improve symptoms of Crohn' s disease. | | 使用 | L-Glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. Optimal cell performance usually requires supplementation of the media with L-glutamine prior to use. | | 使用 | amine protecting agent | | 使用 | L-Glutamine is one of the 20 amino acids encoded by the standard genetic code. Its codons are CAA and CAG. Glutamine is a substance naturally produced in the body to help regulate cell growth and function. There may also be man-made versions of these subs | | 製造方法 | By isolation from sugar beet juice. | | 定義 | ChEBI: An optically active form of glutamine having L-configuration. | | brand name | Nutrestore (Nutritional Restart). | | 生物学の機能 | Glutamine plays a role in a variety of biochemical functions, including :
Protein synthesis, as any other of the 20 proteinogenic amino acids
Regulation of acid-base balance in the kidney by producing ammonium
Cellular energy, as a source, next to glucose
Nitrogen donation for many anabolic processes, including the synthesis of purines
Carbon donation , as a source , refilling the citric acid cycle
Nontoxic transporter of ammonia in the blood circulation. | | Synthesis Reference(s) | Tetrahedron: Asymmetry, 17, p. 245, 2006 DOI: 10.1016/j.tetasy.2005.12.023
Journal of the Chemical Society, p. 3315, 1949 DOI: 10.1039/JR9490003315 | | 一般的な説明 | Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. L-glutamine is the most abundant amino acid in the body. It is essential for the synthesis of L-asparagine. It also helps in muscle growth through protein synthesis and increased growth hormone levels. | | Biochem/physiol Actions | L-Glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. Optimal cell performance usually requires supplementation of the media with L-glutamine prior to use. | | 安全性プロファイル | Mddly toxic by
ingestion. Human systemic effects: euphoria.
When heated to decomposition it emits
toxic fumes of NOx. | | Veterinary Drugs and Treatments | Glutamine has been used as a GI protectant and in an attempt to
enhance GI healing in conditions where GI epithelium is damaged
(Parvo enteritis, chemotherapy, etc.).
A study that evaluated the efficacy of glutamine supplementation
in cats with methotrexate-induced enteritis found no difference
between cats supplemented with glutamine and those that
were not. (Marks, Cook et al. 1999) | | 概要 | 植物中には遊離型で広く存在する | | 純化方法 | Likely impurities are glutamic acid, ammonium pyroglutamate, tyrosine, asparagine, isoglutamine, arginine. Crystallise it from water or aqueous EtOH. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 1929-1925 1961, Beilstein 4 IV 3038.] | | Producing and consuming organs | Producers
Glutamine is synthesized by the enzyme glutamine synthetase from glutamate and ammonia. The most relevant glutamine-producing tissue is the muscle mass, accounting for about 90% of all glutamine synthesized. Glutamine is also released, in small amounts, by the lung and the brain. Although the liver is capable of relevant glutamine synthesis, its role in glutamine metabolism is more regulatory than producing, since the liver takes up large amounts of glutamine derived from the gut.
Consumers
The most eager consumers of glutamine are the cells of intestines, the kidney cells for the acid - base balance, activated immune cells, and many cancer cells. In respect to the last point mentioned, different glutamine analogues, such as DON, Azaserine or Acivicin, are tested as anticancer drugs.
Examples for the usage of glutamine
In catabolic states of injury and illness, glutamine becomes conditionally essential (requiring intake from food or supplements). Glutamine has been studied extensively over the past 10–15 years, and has been shown to be useful in treatment of injuries, trauma, burns, and treatment - related side effects of cancer, as well as in wound healing for postoperative patients. Glutamine is also marketed as a supplement used for muscle growth in weight lifting , body building, endurance, and other sports. Evidence indicates glutamine, when orally loaded, may increase plasma HGH levels by stimulating the anterior pituitary gland. In biological research, L-glutamine is commonly added to the media in cell culture. However, the high level of glutamine in the culture media may inhibit other amino acid transport activities. |
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