LYSINE

CAS NUMBER: 56-87-1

EC NUMBER: 200-294-2

MOLECULAR FORMULA: C6H14N2O2

MOLECULAR WEIGHT: 146.19

IUPAC NAME: (2S)-2,6-diaminohexanoic acid

Lysine is an essential amino acid. The human body cannot make lysine, so it must be eaten in the diet. 
Sources include meat, fish, dairy, and eggs.

Lysine is a building block for making proteins in the body. 
Lysine might also prevent the herpes virus from growing.
People use lysine for cold sores, canker sores, athletic performance, diabetes, and many other conditions, but there is no good scientific evidence to support most of these uses.

Health Benefits of Lysine:
Lysine is a building block for protein. 
Lysine’s an essential amino acid because your body cannot make it, so you need to obtain it from food.

Lysine’s important for normal growth and muscle turnover and used to form carnitine, a substance found in most cells of your body. 
What’s more, it helps transport fats across your cells to be burned for energy.

Lysine is the form of lysine your body can utilize. 
Lysine’s naturally found in food and is the type used in supplements.

*May Protect Against and Treat Cold Sores by Blocking Arginine
Cold sores or fever blisters are symptoms of an infection, often appearing on the lip or the corners of your mouth.
They appear as fluid-filled blisters that can cause discomforts, such as tingling, pain and burning. 
Plus, they may make you feel self-conscious about your appearance.

Cold sores are caused by the herpes simplex virus type 1 (HSV-1), which can hide in your spine. 
In times of stress or if your immune system is weakened, HSV-1 can trigger the development of a cold sore.

Lysine supplements may help prevent HSV-1 from replicating and reduce the duration of a cold sore. 
Lysine’s thought that lysine blocks another amino acid called arginine, which HSV-1 needs in order to multiply 

*Lysine May Reduce Anxiety by Blocking Stress Response Receptors
Lysine may play a role in reducing anxiety.

*Lysine May Improve Calcium Absorption and Retention
Lysine may help your body hold on to calcium.
Lysine’s believed that lysine increases calcium absorption in your gut and helps your kidneys to hold on to the mineral

*Lysine Can Promote Wound Healing by Helping Create Collagen
Lysine can improve wound healing in your body.

In animal tissue, lysine becomes more active at the site of a wound and helps speed up the repair process.
Lysine is required for the formation of collagen, a protein that acts as a scaffold and helps support and give structure to skin and bones.

Lysine itself may also act as a binding agent, thereby increasing the number of new cells at a wound. 
Lysine may even promote the formation of new blood vessels

Top Food Sources and Supplements:
Lysine is found in foods that are naturally high in protein, particularly meat and dairy products, and also in smaller amounts in plant foods.

Here are some great sources of lysine:
-Meat: Beef, chicken and lamb

-Seafood: Mussels, prawns and oysters

-Fish: Salmon, cod, and tuna

-Dairy: Milk, cheese and yogurt

-Vegetables: Potatoes, peppers and leek

-Fruits: Avocado, dried apricots and pears

-Legumes: Soy, kidney beans and chickpeas

-Nuts and seeds: Macadamia, pumpkin seeds and cashews

Cereals are generally a poor source. 
However, quinoa, amaranth and buckwheat contain a decent amount of lysine 

Lysine, is an essential amino acid, meaning it is necessary for human health, but the body cannot make it. 
You have to get lysine from food or supplements. 

Amino acids like lysine are the building blocks of protein. 
Lysine is important for proper growth, and it plays an essential role in the production of carnitine, a nutrient responsible for converting fatty acids into energy and helping lower cholesterol. 

Lysine appears to help the body absorb calcium, and it plays an important role in the formation of collagen, a substance important for bones and connective tissues including skin, tendons, and cartilage.
Most people get enough lysine in their diet. 

Although athletes, burn patients, and vegans who do not eat beans may need more. 
If you do not have enough lysine, you may experience:
-Fatigue

-Nausea

-Dizziness

-Loss of appetite

-Agitation

-Bloodshot eyes

-Slow growth

-Anemia

-Reproductive disorders

For vegans, legumes (beans, peas, and lentils) are the best sources of lysine.

Lysine helps the body absorb calcium and reduces the amount of calcium that is lost in urine. 
Since calcium is crucial for bone health, some researchers think lysine may help prevent bone loss associated with osteoporosis.

Dietary Sources:
Good sources of lysine are high-protein foods such as eggs, meat (specifically red meat, lamb, pork, and poultry), soy, beans and peas, cheese (particularly Parmesan), and certain fish (such as cod and sardines).
Lysine is the limiting amino acid (the essential amino acid found in the smallest quantity in the particular foodstuff) in most cereal grains, but is plentiful in most pulses (legumes).

A vegetarian or low animal protein diet can be adequate for protein, including lysine, if it includes both cereal grains and legumes, but there is no need for the two food groups to be consumed in the same meals.
A food is considered to have sufficient lysine if it has at least 51 mg of lysine per gram of protein (so that the protein is 5.1% lysine).

L-lysine HCl is used as a dietary supplement, providing 80.03% L-lysine.
As such, 1 g of L-lysine is contained in 1.25 g of L-lysine HCl.

Good sources of lysine include foods that are rich in protein, such as:
-Meat, specifically red meat, pork, and poultry
-Cheese, particularly parmesan
-Certain fish, such as cod and sardines
-Eggs
-Soybeans, particularly tofu, isolated soy protein, and defatted soybean flour
-Spirulina
-Fenugreek seed

Brewer's yeast, beans and other legumes, and dairy products also contain lysine.
Lysine (symbol Lys or K)[2] is an α-amino acid that is used in the biosynthesis of proteins. 

Lysine contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain lysyl ((CH2)4NH2), classifying it as a basic, charged (at physiological pH), aliphatic amino acid. 
Lysine is encoded by the codons AAA and AAG. 

Like almost all other amino acids, the α-carbon is chiral and lysine may refer to either enantiomer or a racemic mixture of both. 
For the purpose of this article, lysine will refer to the biologically active enantiomer L-lysine, where the α-carbon is in the S configuration.

The human body cannot synthesize lysine. 
Lysine is essential in humans and must be obtained from the diet. 

In organisms that synthesise lysine, it has two main biosynthetic pathways, the diaminopimelate and α-aminoadipate pathways, which employ distinct enzymes and substrates and are found in diverse organisms. Lysine catabolism occurs through one of several pathways, the most common of which is the saccharopine pathway.
Lysine plays several roles in humans, most importantly proteinogenesis, but also in the crosslinking of collagen polypeptides, uptake of essential mineral nutrients, and in the production of carnitine, which is key in fatty acid metabolism. 

Lysine is also often involved in histone modifications, and thus, impacts the epigenome. 
The ε-amino group often participates in hydrogen bonding and as a general base in catalysis. 

The ε-ammonium group (NH3+) is attached to the fourth carbon from the α-carbon, which is attached to the carboxyl (C=OOH) group.
Due to its importance in several biological processes, a lack of lysine can lead to several disease states including defective connective tissues, impaired fatty acid metabolism, anaemia, and systemic protein-energy deficiency. 

In contrast, an overabundance of lysine, caused by ineffective catabolism, can cause severe neurological disorders.
Lysine was first isolated by the German biological chemist Ferdinand Heinrich Edmund Drechsel in 1889 from the protein casein in milk.
He named it "lysin".
In 1902, the German chemists Emil Fischer and Fritz Weigert determined lysine's chemical structure by synthesizing it.

The human body needs lysine for healthy functioning. 
Lysine is a crucial component of proteins that play a role in helping body tissue grow and recover from damage. 
Other benefits of lysine include:

-helping the body absorb calcium, iron, and zinc
-promoting collagen growth
-helping produce enzymes, antibodies, and hormones
-supporting the immune system

When people do not get enough lysine, they may experience the following symptoms:

-fatigue
-poor concentration
-irritability
-nausea
-red eyes
-hair loss
-anorexia
-inhibited growth
-anemia
-problems with the reproductive system

Lysine is one of the essential amino acids, which are those that the body cannot make and that people need to obtain from dietary sources.
Possible health benefits of lysine and lysine supplements include improving cold sores, reducing blood pressure, and preventing the symptoms of lysine deficiency.

Lysine, also called L-lysine, is an amino acid that is necessary for many bodily functions. 
People describe amino acids as the building blocks of protein because they combine with other compounds to form this macronutrient.

The medical community defines lysine as an essential amino acid because, unlike some other amino acids, the body cannot synthesize it. 
As a result, people need to include it in their diet.

L-lysine is an L-alpha-amino acid; the L-isomer of lysine. 
Lysine has a role as: 
-a micronutrient
-a nutraceutical
-an anticonvulsant
-an Escherichia coli metabolite
-a Saccharomyces cerevisiae metabolite
-a plant metabolite
-a human metabolite
-an algal metabolite
-a mouse metabolite

PHYSICAL PROPERTIES:

-Molecular Weight: 146.19    

-XLogP3: -3        

-Exact Mass: 146.105527694    

-Monoisotopic Mass: 146.105527694    

-Topological Polar Surface Area: 89.3 Ų    

-Physical Description: White crystals or crystalline powder; odourless

-Color: Colorless

-Form: crystals

-Taste: Sweet/bitter

-Melting Point: 224 °C,

-Solubility: 6.84 M

-Vapor Pressure: 5.28e-09 mmHg

Lysine is an aspartate family amino acid, a proteinogenic amino acid, a lysine and a L-alpha-amino acid. 
Lysine is a conjugate base of a L-lysinium(1+). 

Lysine is a conjugate acid of a L-lysinate. 
Lysine is an enantiomer of a D-lysine. 
Lysine is a tautomer of a L-lysine zwitterion.

CHEMICAL PROPERTIES: 

-Heavy Atom Count: 10    

-Formal Charge: 0    

-Complexity: 106    

-Isotope Atom Count: 0    

-Defined Atom Stereocenter Count: 1    

-Undefined Atom Stereocenter Count: 0    

-Defined Bond Stereocenter Count: 0    

-Undefined Bond Stereocenter Count: 0    

-Covalently-Bonded Unit Count: 1    

-Compound Is Canonicalized: Yes

-Hydrogen Bond Donor Count: 3    

-Hydrogen Bond Acceptor Count: 4    

-Rotatable Bond Count: 5

Lysine (abbreviated as Lys or K) is an α-amino acid with the chemical formula HO2CCH(NH2)(CH2)4NH2. 
This amino acid is an essential amino acid, which means that humans cannot synthesize it. 

Lysine's codons are AAA and AAG. 
Lysine is a base, as are arginine and histidine. 

The ε-amino group acts as a site for hydrogen binding and a general base in catalysis. 
Common posttranslational modifications include methylation of the ε-amino group, giving methyl-, dimethyl-, and trimethyllysine. 

The latter occurs in calmodulin. 
Other posttranslational modifications include acetylation. 

Collagen contains hydroxylysine which is derived from lysine by lysyl hydroxylase. 
O-Glycosylation of lysine residues in the endoplasmic reticulum or Golgi apparatus is used to mark certain proteins for secretion from the cell.

Lysine is an essential amino acid. 
Lysine is often added to animal feed.
 

SYNONYMS:

L-lysine
lysine
lysine acid
h-Lys-oh
(S)-Lysine
Aminutrin
(2S)-2,6-diaminohexanoic acid
L-(+)-Lysine
alpha-Lysine
Poly-L-lysine
(S)-2,6-Diaminohexanoic acid
Hydrolysin
Lysinum 
L-lys
Lisina 
(S)-2,6-Diaminocaproic acid
L-Norleucine, 6-amino-
Lysine, L-
Lysinum
(S)-alpha,epsilon-Diaminocaproic acid
Lysine
LYS (IUPAC abbreviation)
L-2,6-Diaminocaproic acid
lysin
Hexanoic acid, 2,6-diamino-, (S)-
lys
a-Lysine
2,6-Diaminohexanoic acid, (S)-
L-Lysin
6-ammonio-L-norleucine
L-Lysine base
L-2,6-Diaminocaproate
Lisina
L-LYSINE, MONOACETATE
(+)-S-Lysine
3H-Lysine
2,6-diaminohexanoate
(S)-(+)-Lysine
EINECS 200-294-2
lysina
L-Lysine, labeled with tritium
Ketporofen lysine
L-aLysine
.alpha.-Lysine
1ozv
1yxd
3h-l-lysine
6-amino-Aminutrin
Poly-(L-lysine)
H-Lys
(-)-lysine
6-amino-L-Norleucine
a,e-Diaminocaproic acid
Lysine (USAN/INN)
Alpha-poly-(L-lysine)
L-2,6-Diainohexanoate
(S)-a,e-Diaminocaproate
L-Lysine, >=97%
Epitope ID:136017
(S)-2,6-Diaminohexanoate
L-2,6-Diainohexanoic acid
(S)-2,6-diamino-Hexanoate
(S)-a,e-Diaminocaproic acid
4-04-00-02717 (Beilstein Handbook Reference)
L-Lysine, analytical standard
L-Lysine, >=98%, FG
(S)-2,6-diamino-Hexanoic acid
L-Lysine, >=98% (TLC)
(2S)-2,6-Diamino-hexanoic acid
L-H2N(CH2)4CH(NH2)COOH
Ethyl3,5-dichloro-4-propoxybenzoate
s5630
.alpha.,.epsilon.-Diaminocaproic acid
L-Lysine solution, purum, 50% in H2O
(S)-.alpha.,.epsilon.-Diaminocaproic acid
L-Lysine, crystallized, >=98.0% (NT)
L-Lysine, Vetec(TM) reagent grade, >=98%
(S)-2,6-Diaminocaproic acid;(S)-(+)-Lysine;Lysine