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L5501

Sigma-Aldrich

L-Lysine

≥98% (TLC)

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Synonym(s):
(S)-2,6-Diaminocaproic acid
Linear Formula:
H2N(CH2)4CH(NH2)CO2H
CAS Number:
56-87-1
Molecular Weight:
146.19
Beilstein:
1722531
EC Number:
200-294-2
MDL number:
MFCD00064433
eCl@ss:
32160406
PubChem Substance ID:
24896404
NACRES:
NA.26

Quality Level

200

Assay

≥98% (TLC)

form

powder

technique(s)

ligand binding assay: suitable

color

white to off-white

mp

215 °C (dec.) (lit.)

solubility

H2O: soluble

SMILES string

NCCCC[C@H](N)C(O)=O

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

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General description

L-lysine contains basic side chain and is hydrophilic in nature. The N-butyl amino group in the side chain is found to be protonated at physiological pH. Upon degradation, L-lysine gives ketone bodies. Transamination of lysine with α-ketoglutarate produces acetoacetyl CoA. L-lysine serves as a precursor for secondary metabolites, such as β-lactam antibiotics. It also serves as a precursor for the biosynthesis of α-aminoadipic acid.

Application

L-Lysine is an essential proteinogenic α amino acid used in a wide range of applications. It has been used:
  • as a supplement in cell culture media
  • as a substrate for enzymes such as L-lysine oxidase (EC 1.4.3.14)
  • as a component of poly-lysine polymers
  • as a substrate for oxidation and glycation mechanism studies
  • in the preparation of cobaltous lysine

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Stryer L. and W. H. Freeman
Biochemistry (3rd Edition), 19-20 (1988)
François-Michel Boisvert et al.
Molecular & cellular proteomics : MCP, 11(3), M111-M111 (2011-09-23)
Measuring the properties of endogenous cell proteins, such as expression level, subcellular localization, and turnover rates, on a whole proteome level remains a major challenge in the postgenome era. Quantitative methods for measuring mRNA expression do not reliably predict corresponding
A L Leitão et al.
Applied microbiology and biotechnology, 56(5-6), 670-675 (2001-10-17)
In beta-lactam producing microorganisms, the first step in the biosynthesis of the beta-lactam ring is the condensation of three amino acid precursors: alpha-aminoadipate, L-cysteine and D-valine. In Nocardia lactamdurans and other cephamycin-producing actinomycetes, alpha-aminoadipate is generated from L-lysine by two
A D Springer et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 30(12), 1235-1242 (1982-12-01)
The introduction of heavy metals directly into living neuronal tissue has received little attention as a method for defining connections in the vertebrate nervous system. Procedures are described for the use of cobaltous-lysine to trace visual pathways with light microscopy.
Devlin T M
Textbook of Biochemistry: With Clinical Correlations (5th ed.), 97-97 (2002)
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