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L5501

Sigma-Aldrich

L-Lysine

≥98% (TLC), suitable for ligand binding assays

Synonym(s):

(S)-2,6-Diaminocaproic acid

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About This Item

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
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24896404
NACRES:
NA.26

product name

L-Lysine, ≥98% (TLC)

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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 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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