丙氨酸

丙氨酸
IUPAC名
Alanine
2-胺基丙酸
别名 2-氨基丙酸
缩写 Ala, A
识别
CAS号 338-69-2（右旋）  checkY
56-41-7（左旋）  checkY
302-72-7（外消旋体）  checkY
PubChem 5950
ChemSpider 64234 （右旋）, 5735 （左旋）, 582 （外消旋体）
SMILES
 
  • O=C(O)C(N)C
InChI
 
  • 1/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)
InChIKey QNAYBMKLOCPYGJ-UHFFFAOYAA
ChEBI 16977
KEGG C01401
IUPHAR配体 720
性质
化学式 C3H7NO2
摩尔质量 89.09 g·mol−1
外观 白色粉末
密度 1.424 g/cm3
熔点 258 °C（531 K）
溶解性（水） 167.2 g/L (25 °C)
log P -0.68[1]
pKa pKa1 = 2.35（-COOH）
pKa2 = 9.87（-NH3+）[2]
磁化率 -50.5·10−6 cm3/mol
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

丙胺酸（Alanine，簡寫为Ala或A）是一種胺基酸，于1850年由阿道夫·斯特雷克（英语：Adolph Strecker）通过乙醛、氨和氢氰酸的反应首次合成。[3][4][5]丙氨酸含有胺基和羧基，二者都與中心碳原子相連，中心碳原子帶有甲基側鏈，IUPAC系統命名為2-胺基丙酸，屬於非極性胺基酸。

鳥類和哺乳類可經由食物中的糖分解所得的丙酮酸合成得到丙氨酸，因此對這些動物來說，丙氨酸為非必需氨基酸。

生物體內合成方式

丙酮酸與麩胺酸藉丙胺酸轉胺酶生成丙胺酸與α-酮戊二酸。

化學合成方式

外消旋的丙胺酸可由乙醛、氯化銨和氰化鈉進行斯特雷克氨基酸合成反应[6]合成。

無圖框
無圖框

參考資料

  1. ^ L-alanine_msds. [2019-08-16]. （原始内容存档于2017-06-16）. 
  2. ^ Haynes, William M. (编). CRC化學和物理手冊 第97版. CRC Press. 2016: 5–88. ISBN 978-1498754286. 
  3. ^ Strecker A. Ueber die künstliche Bildung der Milchsäure und einen neuen, dem Glycocoll homologen Körper [On the artificial formation of lactic acid and a new substance homologous to glycine]. Annalen der Chemie und Pharmacie. 1850, 75 (1): 27–45 [2023-04-24]. doi:10.1002/jlac.18500750103. （原始内容存档于2022-01-07） （德语）.  Strecker names alanine on p. 30.
  4. ^ Strecker A. Ueber einen neuen aus Aldehyd – Ammoniak und Blausäure entstehenden Körper [On a new substance arising from acetaldehyde–ammonia [i.e., 1-aminoethanol] and hydrocyanic acid]. Annalen der Chemie und Pharmacie. 1854, 91 (3): 349–351 [2023-04-24]. doi:10.1002/jlac.18540910309. （原始内容存档于2022-01-06） （德语）. 
  5. ^ Alanine. AminoAcidsGuide.com. 10 June 2018 [14 April 2019]. （原始内容存档于2022-01-06）. 
  6. ^ (1929) "dl-Alanine". Org. Synth. 9: 4; Coll. Vol. 1: 21. 

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