Lysine

Base Information

• Chemical Name: Lysine
• CAS No.: 56-87-1
• Deprecated CAS: 48050-57-3,6899-06-5,280114-50-3,1150316-18-9,1153953-95-7,2087491-46-9,2139267-51-7,2566526-81-4,1150316-18-9,280114-50-3,6899-06-5
• Molecular Formula: C6H14N2O2
• Molecular Weight: 146.189
• Hs Code.: 2922411000
• European Community (EC) Number: 200-294-2
• UNII: K3Z4F929H6
• DSSTox Substance ID: DTXSID6023232
• Nikkaji Number: J9.176F
• Wikipedia: Lysine
• Wikidata: Q20816880
• NCI Thesaurus Code: C29171
• RXCUI: 6536
• Pharos Ligand ID: NQYLK44FVG4U
• Metabolomics Workbench ID: 37121
• ChEMBL ID: CHEMBL8085
• Mol file: 56-87-1.mol

Synonyms:Acetate, Lysine;Enisyl;L Lysine;L-Lysine;Lysine;Lysine Acetate;Lysine Hydrochloride

Chemical Property of Lysine

Chemical Property:

• Appearance/Colour: white or almost white crystalline powder
• Melting Point: 215 °C (dec.)(lit.)
• Refractive Index: 26 ° (C=2, 5mol/L HCl)
• Boiling Point: 311.542 °C at 760 mmHg
• Flash Point: 142.216 °C
• PSA: 89.34000
• Density: 1.125 g/cm³
• LogP: 0.92790
• XLogP3: -3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 146.105527694
• Heavy Atom Count: 10
• Complexity: 106

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C(CCN)CC(C(=O)O)N
• Isomeric SMILES: C(CCN)C[C@@H](C(=O)O)N
• Recent ClinicalTrials: Determinants of Alpha-aminoadipic Acid (2-AAA) and Relationship to Diabetes: Study 3
• Recent EU Clinical Trials: AN EXPLORATORY OPEN LABEL STUDY OF ADJUNCTIVE L-LYSINE TREATMENT IN PATIENTS WITH SCHIZOPHRENIA
• Essential Amino Acid: Lysine is an indispensable amino acid (IAA) and is essential in our diets, meaning it must be obtained from food as the body cannot synthesize it. Its importance was demonstrated by William Rose and colleagues in 1955, showing that lysine is required in the human diet for positive nitrogen balance.
• Amino Acid Score (AAS): Lysine is singled out as an important IAA because it is present in limited amounts in many food sources, particularly grains. The FAO/WHO has established an amino acid score based on the ideal composition of each IAA in protein. Lysine concentration in protein is compared to an ideal protein, and its AAS should ideally be 45 mg/g protein for adults.
• Protein Synthesis: Lysine plays a crucial role in protein synthesis. Proteins cannot be synthesized if any essential amino acid, like lysine, is limited in availability. Limiting lysine intake results in reduced protein synthesis and can lead to a negative nitrogen balance.
• Lysine Deficiency: Foods like grains and peanut butter have lysine concentrations below the ideal level, resulting in AAS scores below 1. Lysine deficiency can be overcome by consuming larger amounts of protein or by combining lysine-deficient foods with lysine-rich foods, such as beans, to achieve a balanced amino acid intake.
• Role in Animals: Lysine cannot be synthesized by mammals and is therefore essential in their diets as well. Lysine is strictly indispensable and does not participate in transamination reactions. It serves as a precursor for protein synthesis and is catabolized through the saccharopine pathway, primarily in the liver.
• Biosynthesis of Carnitine: Lysine is also a precursor for the biosynthesis of carnitine, an important compound involved in fatty acid metabolism. Carnitine plays a crucial role in transporting fatty acids into the mitochondria for 尾-oxidation, contributing to energy production.

Technology Process of Lysine

There total 285 articles about Lysine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

ethanol (64-17-5) + L-lysine n-propyl ester (57590-09-7) → L-Lysine ethyl ester (4117-33-3) + L-lysine (56-87-1,3506-25-0)

Guidance literature:

immobilized trypsin; at 25 ℃; 5percent 0.1 M acetate buffer, pH:6.2;

DOI:10.1248/cpb.32.4514

Reference yield:

L-lysine-p-nitroanilide (19826-45-0,6184-11-8) → L-lysine (56-87-1,3506-25-0) + 4-nitro-aniline (100-01-6,104810-17-5)

Guidance literature:

With Streptomyces griseus dizinc aminopeptidase; water; calcium(II) ion; In various solvent(s); at 30 ℃; pH=8.0; Enzyme kinetics;

DOI:10.1002/(SICI)1521-3773(19991004)38:19<2914::AID-ANIE2914>3.0.CO;2-P

Reference yield:

5,5'-dithiobis-(2-nitrobenzoic acid) (69-78-3) + L-Lys-S-(N-acetyl)cysteamine → L-lysine (56-87-1,3506-25-0) + 2-nitro-5-mercaptobenzoic acid anion (18430-02-9,39509-22-3) + 2-aminocaprolactam (21568-87-6)

Guidance literature:

In aq. buffer; at 30 ℃; pH=7.5; Kinetics;

DOI:10.1002/cbic.201500701

upstream raw materials:

4-pentenal

alpha-aminopimelic acid

pentane-1,1,5-tricarboxylic acid

diethyl 2-acetamido-2-(3-cyanopropyl)malonate

Downstream raw materials:

L-lysine

N^α,N^ε-bis-[(2,4,5-trichloro-phenoxy)-acetyl]-L-lysine

Δ¹-piperidine-2-carboxylic acid

1,5-diaminopentane

Refernces

• 1、 De Cesare, Silvia,McKenna, Catherine A.,Mulholland, Nicholas,Murray, Lorna,Bella, Juraj,Campopiano, Dominic J.. "Direct monitoring of biocatalytic deacetylation of amino acid substrates by1H NMR reveals fine details of substrate specificity". supporting information. p. 4904 - 4909. Retrieved 2021/06/16.
• 2、 Pala, Nicolino,Esposito, Francesca,Tramontano, Enzo,Singh, Pankaj Kumar,Sanna, Vanna,Carcelli, Mauro,Haigh, Lisa D.,Satta, Sandro,Sechi, Mario. "Development of a Raltegravir-based Photoaffinity-Labeled Probe for Human Immunodeficiency Virus-1 Integrase Capture". supporting information. p. 1986 - 1992. Retrieved 2020/11/09.