Synonym
Val-pro-pro; L-Proline, 1-(1-L-valyl-L-prolyl)-; L-Valyl-L-prolyl-L-proline; L-Proline, L-valyl-L-prolyl-
IUPAC/Chemical Name
(2S)-1-[(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylic acid
InChi Key
DOFAQXCYFQKSHT-SRVKXCTJSA-N
InChi Code
InChI=1S/C15H25N3O4/c1-9(2)12(16)14(20)17-7-3-5-10(17)13(19)18-8-4-6-11(18)15(21)22/h9-12H,3-8,16H2,1-2H3,(H,21,22)/t10-,11-,12-/m0/s1
SMILES Code
O=C([C@H]1N(C([C@H]2N(C([C@@H](N)C(C)C)=O)CCC2)=O)CCC1)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
311.38
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: Chakrabarti S, Jahandideh F, Davidge ST, Wu J. Milk-Derived Tripeptides IPP (Ile-Pro-Pro) and VPP (Val-Pro-Pro) Enhance Insulin Sensitivity and Prevent Insulin Resistance in 3T3-F442A Preadipocytes. J Agric Food Chem. 2018 Oct 3;66(39):10179-10187. doi: 10.1021/acs.jafc.8b02051. Epub 2018 Sep 20. PubMed
PMID: 30160110.
2: Miyazaki H, Nakamura T, Ohki K, Nagai K. Effects of the bioactive peptides Ile-Pro-Pro and Val-Pro-Pro upon autonomic neurotransmission and blood pressure in spontaneously hypertensive rats. Auton Neurosci. 2017 Dec;208:88-92. doi: 10.1016/j.autneu.2017.09.017. Epub 2017 Sep 29. PubMed PMID: 28988803.
3: Kurosawa MT, Nakamura Y, Yamamoto N, Yamada K, Iketani T. Effects of Val-Pro-Pro and Ile-Pro-Pro on nondipper patients: a preliminary study. J Med Food. 2011 May;14(5):538-42. doi: 10.1089/jmf.2010.0343. Epub 2011 Apr 11. PubMed PMID: 21480799.
4: Turpeinen AM, Ehlers PI, Kivimäki AS, Järvenpää S, Filler I, Wiegert E, Jähnchen E, Vapaatalo H, Korpela R, Wagner F. Ile-Pro-Pro and Val-Pro-Pro tripeptide-containing milk product has acute blood pressure lowering effects in mildly hypertensive subjects. Clin Exp Hypertens. 2011;33(6):388-96. doi: 10.3109/10641963.2010.549267. Epub 2011 Jun 7. PubMed PMID: 21649532.
5: Nonaka A, Nakamura T, Hirota T, Matsushita A, Asakura M, Ohki K, Kitakaze M. The milk-derived peptides Val-Pro-Pro and Ile-Pro-Pro attenuate arterial dysfunction in L-NAME-treated rats. Hypertens Res. 2014 Aug;37(8):703-7. doi: 10.1038/hr.2014.72. Epub 2014 Apr 3. PubMed PMID: 24694646.
