Synonym
Lysyl-tyrosyl-lysine
IUPAC/Chemical Name
L-Lysine, N2-(N-L-lysyl-L-tyrosyl)-
InChi Key
WINFHLHJTRGLCV-BZSNNMDCSA-N
InChi Code
InChI=1S/C21H35N5O5/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/h7-10,16-18,27H,1-6,11-13,22-24H2,(H,25,29)(H,26,28)(H,30,31)/t16-,17-,18-/m0/s1
SMILES Code
NCCCC[C@@H](C(O)=O)NC([C@H](CC1=CC=C(O)C=C1)NC([C@H](CCCCN)N)=O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
437.54
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Prell JS, O'Brien JT, Holm AI, Leib RD, Donald WA, Williams ER. Electron capture by a hydrated gaseous peptide: effects of water on fragmentation and molecular survival. J Am Chem Soc. 2008 Sep 24;130(38):12680-9. doi: 10.1021/ja8022434. Epub 2008 Aug 30. PubMed PMID: 18761457; PubMed Central PMCID: PMC2673717.
2: Zhang J, Kalonia DS. The effect of neighboring amino acid residues and solution environment on the oxidative stability of tyrosine in small peptides. AAPS PharmSciTech. 2007 Dec 7;8(4):E102. doi: 10.1208/pt0804102. PubMed PMID: 18181523; PubMed Central PMCID: PMC2750355.
3: Cheng CT, Lo V, Chen J, Chen WC, Lin CY, Lin HC, Yang CH, Sheh L. Synthesis and DNA nicking studies of a novel cyclic peptide: cyclo[Lys-Trp-Lys-Ahx-]. Bioorg Med Chem. 2001 Jun;9(6):1493-8. PubMed PMID: 11408167.
4: Kato-Toma Y, Ishiguro M. Reaction of Lys-Tyr-Lys triad mimics with benzylpenicillin: insight into the role of Tyr150 in class C beta-lactamase. Bioorg Med Chem Lett. 2001 May 7;11(9):1161-4. PubMed PMID: 11354367.
5: Limoli CL, Wu CC, Milligan JR, Ward JF. Photochemical production of uracil quantified in bromodeoxyuridine-substituted SV40 DNA by uracil DNA glycosylase and a lysyl-tyrosyl-lysine tripeptide. Mutagenesis. 1997 Nov;12(6):443-7. PubMed PMID: 9412998.
6: Barthwal R, Kukreti S, Mujeeb A. A 500 MHz proton NMR study of interaction of tripeptides Lys-Tyr-Lys and Lys-Phe-Lys with deoxydinucleotide d-CpG. Indian J Biochem Biophys. 1992 Oct;29(5):394-401. PubMed PMID: 1289228.
7: Barthwal R, Mujeeb A, Kukreti S, Gupta A, Govil G. A 500 MHz proton NMR study of stacking interactions: binding of tripeptide Lys-Tyr-Lys to tetradeoxynucleotide d-GpCpGpC. J Mol Recognit. 1991 Mar-Jun;4(2-3):45-52. PubMed PMID: 1810346.
8: Favaudon V. Radiation-induced crosslinking between poly(deoxyadenylic-deoxythymidylic acid) and tripeptides containing aromatic residues. Int J Radiat Biol. 1989 Mar;55(3):353-64. PubMed PMID: 2564033.
