Synonym
Diprotin B; H-Val-Pro-Leu-OH; valyl-prolyl-leucine; VAL-PRO-LEU; L-valyl-L-prolyl-L-leucine
IUPAC/Chemical Name
(2S)-2-[[(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoic acid
InChi Key
NHXZRXLFOBFMDM-AVGNSLFASA-N
InChi Code
InChI=1S/C16H29N3O4/c1-9(2)8-11(16(22)23)18-14(20)12-6-5-7-19(12)15(21)13(17)10(3)4/h9-13H,5-8,17H2,1-4H3,(H,18,20)(H,22,23)/t11-,12-,13-/m0/s1
SMILES Code
CC(C)C[C@@H](C(O)=O)NC([C@H]1N(C([C@H](C(C)C)N)=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
2934.99.03.00
Biological target:
Diprotin B is a dipeptidyl aminopeptidase IV (DPP IV) inhibitor.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
327.43
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 |
Formulation protocol:
TBD
1: Rahfeld J, Schierhorn M, Hartrodt B, Neubert K, Heins J. Are diprotin A (Ile-Pro-Ile) and diprotin B (Val-Pro-Leu) inhibitors or substrates of dipeptidyl peptidase IV? Biochim Biophys Acta. 1991 Jan 29;1076(2):314-6. PubMed PMID: 1671823.
2: Hiramatsu H, Kyono K, Yamamoto A, Saeki K, Shima H, Sugiyama S, Inaka K, Shimizu R. Crystal structures of human dipeptidyl peptidase IV in its apo and diprotin B-complexed forms. Acta Biochim Biophys Sin (Shanghai). 2007 May;39(5):335-43. PubMed PMID: 17492130.
3: Umezawa H, Aoyagi T, Ogawa K, Naganawa H, Hamada M, Takeuchi T. Diprotins A and B, inhibitors of dipeptidyl aminopeptidase IV, produced by bacteria. J Antibiot (Tokyo). 1984 Apr;37(4):422-5. PubMed PMID: 6427168.
4: Endröczi E, Hepp J, Sasváry M, Walentin S, Lévay G. Dipeptidyl peptidase IV (DP IV) and superoxide dismutase activity in thymus-derived lymphocytes: effects of inhibitory peptides and Zn2+ in vitro. Acta Physiol Hung. 1990;75(1):35-44. PubMed PMID: 1971138.
5: Guionie O, Moallic C, Niamké S, Placier G, Sine JP, Colas B. Identification and primary characterization of specific proteases in the digestive juice of Archachatina ventricosa. Comp Biochem Physiol B Biochem Mol Biol. 2003 Jul;135(3):503-10. PubMed PMID: 12831770.
6: Land CM, Kinsel GR. The mechanism of matrix to analyte proton transfer in clusters of 2,5-dihydroxybenzoic acid and the tripeptide VPL. J Am Soc Mass Spectrom. 2001 Jun;12(6):726-31. PubMed PMID: 11401163.
7: Sedo A, Revoltella RP. Detection of dipeptidyl peptidase IV in glioma C6 and neuroblastoma SK-N-SH cell lines. Biochem Cell Biol. 1995 Jan-Feb;73(1-2):113-5. PubMed PMID: 7662310.
8: Malík R, Vlasicová L, Kadlecová L, Sedo A. Heterogeneity of dipeptidyl peptidase IV from C6 rat glioma cells. Neoplasma. 2000;47(2):96-9. PubMed PMID: 10985474.
9: Yassin FH, Marynick DS. Computational study of matrix-peptide interactions in MALDI mass spectrometry: Interactions of 2,5- and 3,5-dihydroxybenzoic acid with the tripeptide valine-proline-leucine. J Phys Chem A. 2006 Mar 16;110(10):3820-5. PubMed PMID: 16526668.
