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Merck
CN

L3271

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)
NACRES:
NA.26
PubChem Substance ID:
24896335
UNSPSC Code:
12352209
MDL number:
MFCD00079406

Key Documents

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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

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 key

OXXOYNFTOCTMGG-UVJOBNTFSA-N

assay

≥97% (HPLC)

form

powder

color

white to off-white

storage temp.

−20°C

Related Categories

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF3997
BCCB5733
BCBW6337
BCBS0872V
BCBS0872

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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
V Favaudon
International journal of radiation biology, 55(3), 353-364 (1989-03-01)
OH.-induced covalent peptide-nucleotide adducts have been isolated by reverse-phase chromatography from the enzymic hydrolyzates of gamma-ray irradiated solutions containing double-stranded poly(deoxyadenylic-deoxythymidylic acid) and one of the tripeptides, lysyl-tryptophyl-lysine or lysyl-tyrosyl-lysine. Numerous compounds were formed, resulting presumably from different modes of
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
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
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)
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