Synonym
Lysyl-alanyl-alanine
IUPAC/Chemical Name
D-Alanine, N-(N-L-lysyl-D-alanyl)-
InChi Key
FZIJIFCXUCZHOL-HLTSFMKQSA-N
InChi Code
InChI=1S/C12H24N4O4/c1-7(10(17)16-8(2)12(19)20)15-11(18)9(14)5-3-4-6-13/h7-9H,3-6,13-14H2,1-2H3,(H,15,18)(H,16,17)(H,19,20)/t7-,8-,9+/m1/s1
SMILES Code
C[C@H](C(O)=O)NC([C@@H](C)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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
288.35
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: Setnicka V, Hlavácek J, Urbanová M. Cationic oligopeptides with the repeating sequence L-lysyl-L-alanyl-L-alanine: conformational and thermal stability study using optical spectroscopic methods. J Pept Sci. 2009 Aug;15(8):533-9. doi: 10.1002/psc.1154. PubMed PMID: 19579212.
2: Shepherd J, Gale T, Jensen KB, Kilburn JD. Synthesis of unsymmetrical tweezer receptor libraries and identification of receptors for lys-D-ala-D-ala in aqueous solution. Chemistry. 2006 Jan 11;12(3):713-20. PubMed PMID: 16224810.
3: Williams DH, Davies NL, Koivisto JJ. Importance of structural tightening, as opposed to partially bound States, in the determination of chemical shift changes at noncovalently bonded interfaces. J Am Chem Soc. 2004 Nov 3;126(43):14267-72. PubMed PMID: 15506794.
4: Vondrásek J, Sponar J, Hobza P. An empirical potential study of the interaction of L-lysine-L-alanine-L-alanine tripeptide with four models of B-DNA with different compositions. J Biomol Struct Dyn. 1994 Feb;11(4):869-80. PubMed PMID: 8204220.
5: Fernandez Y, Perez JJ, Ricart JM. Molecular mechanical study of the stability of the Lys-Ala-Ala tripeptide dimer. Int J Biol Macromol. 1992 Jun;14(3):154-60. PubMed PMID: 1390447.
6: Kelly JA, Knox JR, Zhao H, Frère JM, Ghaysen JM. Crystallographic mapping of beta-lactams bound to a D-alanyl-D-alanine peptidase target enzyme. J Mol Biol. 1989 Sep 20;209(2):281-95. PubMed PMID: 2585485.
7: Verdaguer N, Urpí L, Fita I, Subirana JA. Molecular structure of L-lysyl-L-alanyl-L-alanine: a tripeptide found in histone H1. Biopolymers. 1988 Dec;27(12):1887-96. PubMed PMID: 3240357.
8: Arán V, Rodríguez-Tébar A, Vázquez D. Labelling of penicillin-binding proteins with a photoreactive peptidoglycan-peptide analogue. Eur J Biochem. 1984 Nov 2;144(3):613-6. PubMed PMID: 6386475.
