L-lysine
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L-lysine

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L-lysine is an essential amino acid obtained from some foods, especially red meats, fish, and dairy products. It acts as a nutritional supplement.

Category
L-Amino Acids
Catalog number
BAT-014299
CAS number
56-87-1
Molecular Formula
C6H14N2O2
Molecular Weight
146.19
L-lysine
IUPAC Name
(2S)-2,6-diaminohexanoic acid
Synonyms
Lysine; H-Lys-OH
Related CAS
57282-49-2 (acetate salt) 39665-12-8 (hydrate)
Appearance
White Crystalline Powder
Purity
>98%
Density
1.136±0.1 g/cm3
Melting Point
215 °C (dec.)
Boiling Point
311.5°C at 760mmHg
Storage
Store at 2-8°C
Solubility
H2O: 0.1 g/mL, clear, colorless
InChI
InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1
InChI Key
KDXKERNSBIXSRK-YFKPBYRVSA-N
Canonical SMILES
C(CCN)CC(C(=O)O)N

L-lysine is one of the nine essential amino acids that the human body cannot synthesize on its own. It plays a key role in a variety of physiological functions and provides a multitude of benefits in various fields, including human health, animal nutrition, and industrial applications. With the structure of α,ε-diaminohexanoic acid, L-lysine (often abbreviated to lysine) is essential for growth, tissue repair, and the production of various biochemicals.

1. Protein Synthesis and Muscle Health: L-lysine is essential for protein synthesis, an essential process that supports growth and repair in the body. As a building block of protein, it contributes significantly to muscle health and recovery, making it essential for athletes and those who regularly engage in physical activity. Supplementation with L-lysine can enhance muscle recovery, reduce fatigue, and minimize the risk of injury by supporting the repair of muscle tissue.

2. Herpes Simplex Virus (HSV) Management: One of the more well-studied applications of L-lysine in human health is for the management and prevention of outbreaks of the herpes simplex virus (HSV), particularly HSV-1, which causes cold sores. L-lysine competes with the amino acid arginine, which is required for HSV replication. By increasing L-lysine intake, viral replication can be inhibited, thereby reducing the severity and frequency of outbreaks. Many people take L-lysine supplements as a preventative measure against cold sores.

3. Bone Health: L-lysine plays a key role in calcium absorption, which is essential for maintaining bone health and preventing osteoporosis. It increases intestinal absorption of calcium and reduces renal excretion, thereby maintaining optimal bone density. By enhancing collagen formation, L-lysine also helps maintain the structural integrity of bones.

4. Livestock Feed Supplement: L-lysine is an essential dietary component in animal nutrition, especially for monogastric animals such as pigs and poultry. These animals are unable to synthesize lysine on their own; therefore, lysine supplementation is essential to ensure their growth, development, and overall productivity. L-lysine enhances protein synthesis in livestock, thereby promoting muscle development and improving feed conversion ratio (FCR). This, in turn, makes meat production more sustainable and cost-effective.

5. Pet Nutrition: In pet nutrition, especially for cats and dogs, L-lysine is used to support overall health and manage certain health conditions. For example, in cats, L-lysine supplementation is thought to help control feline herpes virus (FHV) infection, similar to its role in controlling HSV in humans. Pets that do not have adequate dietary intake of essential amino acids can benefit from L-lysine supplementation to support their immune system, muscle health, and overall vitality.

6. Biotechnology Production: In the biotechnology sector, L-lysine has become an important compound for the production of a variety of biochemicals. L-lysine is produced on an industrial scale using microbial fermentation processes using genetically engineered bacteria such as Corynebacterium glutamicum. This microbial synthesis of L-lysine is not only economically viable but also environmentally sustainable, supporting industrial-scale production of this essential amino acid for a variety of uses.

7. Pharmaceutical Industry: L-lysine is also used as an excipient in drug formulations in the pharmaceutical industry. It acts as a stabilizer and improves the bioavailability of various drugs. For example, it is often included in the formulation of ophthalmic drugs and certain antibiotics to improve their stability and efficacy.

8. Nutritional Supplements: Given its numerous health benefits, L-lysine is a common ingredient in dietary and nutritional supplements. It is available in a variety of forms, including tablets, capsules, and powders, for individuals who wish to increase their dietary intake of this important amino acid. L-lysine supplements are popular among vegans and vegetarians who may not be getting enough lysine in their diets because plant proteins are lower in content than animal proteins.

1.Origin of pK
Wu X;Lee J;Brooks BR J Phys Chem B. 2017 Apr 20;121(15):3318-3330. doi: 10.1021/acs.jpcb.6b08249. Epub 2016 Oct 18.
Protein internal ionizable groups can exhibit large shifts in pK;a; values. Although the environment and interaction changes have been extensively studied both experimentally and computationally, direct calculation of pK;a; values of these internal ionizable groups in explicit water is challenging due to energy barriers in solvent interaction and in conformational transition. The virtual mixture of multiple states (VMMS) method is a new approach designed to study chemical state equilibrium. This method constructs a virtual mixture of multiple chemical states in order to sample the conformational space of all states simultaneously and to avoid crossing energy barriers related to state transition. By applying VMMS to 25 variants of staphylococcal nuclease with lysine residues at internal positions, we obtained the pK;a; values of these lysine residues and investigated the physics underlining the pK;a; shifts. Our calculation results agree reasonably well with experimental measurements, validating the VMMS method for pK;a; calculation and providing molecular details of the protonation equilibrium for protein internal ionizable groups. Based on our analyses of protein conformation relaxation, lysine side chain flexibility, water penetration, and the microenvironment, we conclude that the hydrophobicity of the microenvironment around the lysine side chain (which affects water penetration differently for different protonation states) plays an important role in the pK;a; shifts.
2.Nitrogen regulator GlnR directly controls transcription of genes encoding lysine deacetylases in Actinobacteria.
Xu Y;You D;Ye BC Microbiology. 2017 Nov;163(11):1702-1710. doi: 10.1099/mic.0.000553. Epub 2017 Oct 23.
N-Lysine acetylation is a dynamic, reversible and regulatory post-translational modification (PTM) in prokaryotes, which integrates and coordinates metabolisms responding to environmental clues. However, the molecular mechanism underlying the signalling pathway from nutrient sensing to protein acetylation remains incompletely understood in micro-organisms. Here we found that global nitrogen regulator GlnR directly controls transcription of genes encoding lysine deacetylases in Actinobacteria. Electrophoretic mobility shift assays and real-time PCR (RT-PCR) in three Actinobacteria species (Saccharopolyspora erythraea, Streptomyces coelicolor and Mycobacterium smegmatis) revealed that GlnR regulator protein is able to interact with the promoter regions of these genes and activate their transcription. Furthermore, it was demonstrated that cellular acetylation status (acetylome) is modulated by extracellular nitrogen availability. Our results present an example of the novel complete signal transduction mechanism of regulating protein deacetylation through a nutrient-sensing pleiotropic regulator in response to nutrient availability.
3.Maleimide-functionalized closo-dodecaborate albumin conjugates (MID-AC): Unique ligation at cysteine and lysine residues enables efficient boron delivery to tumor for neutron capture therapy.
Kikuchi S;Kanoh D;Sato S;Sakurai Y;Suzuki M;Nakamura H J Control Release. 2016 Sep 10;237:160-7. doi: 10.1016/j.jconrel.2016.07.017. Epub 2016 Jul 12.
Maleimide-conjugating closo-dodecaborate sodium form 5c (MID) synthesized by the nucleophilic ring-opening reaction of closo-dodecaborate-1,4-dioxane complex 2 with tetrabutylammonium (TBA) azide was found to conjugate to free SH of cysteine and lysine residues in BSA under physiological conditions, forming highly boronated BSA that showed high and selective accumulation in tumor and significant tumor growth inhibition in colon 26 tumor-bearing mice subjected to thermal neutron irradiation.
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