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L3271

Sigma-Aldrich

Lys-Tyr-Lys acetate salt

≥97% (HPLC)

Synonym(s):

Lysyltyrosyllysine, acetate

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About This Item

Empirical Formula (Hill Notation):
C21H35N5O5 · xC2H4O2
Molecular Weight:
437.53 (free base basis)
MDL number:
MFCD00079406
UNSPSC Code:
12352209
PubChem Substance ID:
24896335
NACRES:
NA.26

Assay

≥97% (HPLC)

form

powder

color

white to off-white

storage temp.

−20°C

SMILES string

CC(O)=O.NCCCC[C@H](N)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CCCCN)C(O)=O

InChI

1S/C21H35N5O5.C2H4O2/c22-11-3-1-5-16(24)19(28)26-18(13-14-7-9-15(27)10-8-14)20(29)25-17(21(30)31)6-2-4-12-23;1-2(3)4/h7-10,16-18,27H,1-6,11-13,22-24H2,(H,25,29)(H,26,28)(H,30,31);1H3,(H,3,4)/t16-,17-,18-;/m0./s1

InChI key

OXXOYNFTOCTMGG-UVJOBNTFSA-N

Related Categories

Amino Acid Sequence

Lys-Tyr-Lys

Application

Lysyltyrosyllysine (Lys-Tyr-Lys, KYK) is used together with uracil DNA glycosylase to quantify uracil. Lysyltyrosyllysine is also used as a model peptide to study free radical oxidation and electron capture mechanisms.

Biochem/physiol Actions

Tripeptide can induce nicks at apurinic/apyrimidinic sites in circular DNA.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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Arg-Gly-Asp ≥97% (TLC)

Sigma-Aldrich

A8052

Arg-Gly-Asp

Gly-Tyr

Sigma-Aldrich

G3502

Gly-Tyr

The effect of neighboring amino acid residues and solution environment on the oxidative stability of tyrosine in small peptides.
Zhang J, Kalonia DS.
AAPS PharmSci, 8, E102-E102 (2007)
James S Prell et al.
Journal of the American Chemical Society, 130(38), 12680-12689 (2008-09-03)
The effects of water on electron capture dissociation products, molecular survival, and recombination energy are investigated for diprotonated Lys-Tyr-Lys solvated by between zero and 25 water molecules. For peptide ions with between 12 and 25 water molecules attached, electron capture
R Barthwal et al.
Journal of molecular recognition : JMR, 4(2-3), 45-52 (1991-03-01)
The complete sequential assignment and conformation of d-GpCpGpC in D2O has been determined from 1D NMR spectra at 285-320 K and room temperature 2D-COSY and NOESY spectra. The tetradeoxynucleotide exists primarily as a right handed double helix at 285 K
C L Limoli et al.
Mutagenesis, 12(6), 443-447 (1997-12-31)
Exposure to UVA radiation of SV40 DNA substituted with bromodeoxyuridine (BrdU) in the presence of Hoechst dye 33258 results in the production of uracil. The yield of uracil was determined by measuring the increase in the single-strand break (SSB) yield
J Pierre et al.
The Journal of biological chemistry, 256(20), 10217-10220 (1981-10-25)
Tripeptides containing aromatic residues between basic ones, such as Lys-Trp-Lys and Lys-Tyr-Lys can nick supercoiled or relaxed DNAs containing apurinic/apyrimidinic sites (AP-sites). The nicking, which is ionic strength-dependent, occurs at AP-sites, since native PM2 DNA is not hydrolyzed. The nicking
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