Lysine
Lysine was discovered in 1889 by Drechsel, who first isolated it from casein (milk protein). Three years later, its structure was elucidated. Then, Vickery and Leavenworth prepared crystalline lysine in 1928. Finally, Fischer and Weigert accomplished the synthesis of lysine by treating 7-cyanopropylmalonic ester with nitrous acid.
Chemical Structure of L-Lysine
Identifiers and properties of Lysine
IUPAC Name: (2S)-2,6-Diaminohexanoic acid
Symbol: Three-letter code - Lys. One-letter code - K
Molecular Weight (Molar Mass): 146.18756 g/mol
Molecular Formula (Structural Formula): C6H14N2O2
Canonical SMILES: C(CCN)CC(C(=O)O)N
Isomeric SMILES: C(CCN)C[C@@H](C(=O)O)N
InChIKey Identifier: KDXKERNSBIXSRK-RJFJIGAVDG
CAS Number: 56-87-1
MDL Number: MFCD00064433
Melting point: 215 °C
RNA codons: AAA, AAG
Solubility in water: 1500 g/L (25 °C); pKa - 2,18; pKb - 8,95
Rf value in n-butanol/acetic acid/water = 12:3:5 - 0.14
2D Molfile: Get the molfile
3D PDB file: Get the PDB file
Other names: alpha-Lysine; (+)-S-Lysine; (S)-2,6-Diamino-hexanoic acid
What are the functions of the Lysine?
Lysine is recognized as an amino acid necessary as a building block for all proteins in your body. It plays a major role in calcium absorption, as well as in helping building muscle protein. Besides, Lysine aids in recovering from surgery or traumas and helps your body produce hormones, enzymes, and antibodies. This amino acid was also proved to depress the central nervous system while having antiseizure properties.
Lysine is an essential amino acid, implying that it is important for human health, though our body cannot produce it. Therefore, it has to be obtained from food. Lysine is a type of amino acids that are the building blocks of proteins. It is vital for proper growth and plays an important role in the production of carnitine, which is a nutrient that transforms fatty acids into energy and lowers cholesterol levels. In addition, this amino acid is proved to help the human body absorb calcium, while playing an essential role in the formation of collagen - a substance necessary for both bones and connective tissues like skin, cartilage, and tendon.
Naturally, people obtain enough Lysine from foods, but athletes, vegans, and people who do not like beans may need more. A lack of Lysine in the body can cause such symptoms as slow growth, fatigue, nausea, dizziness, and even reproductive disorders. Vegans are recommended to consume more legumes like beans, peas, and lentils to obtain enough Lysine.
Benefits of Lysine
There are numerous studies proving that Lysine may help prevent outbreaks of cold sores and genital herpes. Other studies revealed that it helps the body absorb calcium and decrease the amount of calcium lost in urine. Since calcium is essential for bone health, you can conclude that Lysine may help prevent the bone loss caused by osteoporosis.
Food sources
Here is a list of foods that are good sources of lysine.
Meat and Poultry. Chicken breast: About 3.6 grams per 100 grams. Turkey: Approximately 2.8 grams per 100 grams. Beef: Contains around 2.4 grams per 100 grams.
Fish. Tuna: About 2.3 grams per 100 grams. Salmon: Contains around 2.6 grams per 100 grams.
Dairy Products. Yogurt: Approximately 2 grams per 6-ounce (170-gram) container. Cheese (Parmesan, Gouda, etc.): Varies but can range from 0.5 to 1 gram per ounce.
Eggs. One large egg contains about 0.6 grams of lysine.
Legumes. Lentils: Approximately 1.3 grams per 100 grams. Chickpeas: About 1.4 grams per 100 grams. Black beans: Contains around 1.3 grams per 100 grams.
Quinoa is a good plant-based source, providing about 1.9 grams per 100 grams.
Soy Products. Tofu: Approximately 1.5 grams per 100 grams. Tempeh: Contains around 2.2 grams per 100 grams. Soybeans: About 1.3 grams per 100 grams.
Nuts and Seeds. Pumpkin seeds: Approximately 1.1 grams per ounce. Peanuts: About 1.5 grams per ounce.
It's important to note that lysine content can vary based on factors such as cooking methods and the specific type or cut of the food. Additionally, individual dietary needs may vary, so it's advisable to consult with a healthcare professional or a registered dietitian to ensure you are meeting your specific nutritional requirements. If you have specific dietary restrictions or conditions, it's always a good idea to tailor your diet to your individual needs.