Synonym
Phenylalanylproline; D-Phe-pro; L-Phe-pro;
IUPAC/Chemical Name
D-phenylalanyl-L-proline
InChi Key
WEQJQNWXCSUVMA-NEPJUHHUSA-N
InChi Code
InChI=1S/C14H18N2O3/c15-11(9-10-5-2-1-3-6-10)13(17)16-8-4-7-12(16)14(18)19/h1-3,5-6,11-12H,4,7-9,15H2,(H,18,19)/t11-,12+/m1/s1
SMILES Code
O=C(O)[C@H]1N(C([C@@H](CC2=CC=CC=C2)N)=O)CCC1
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
262.30
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: Li Y, Wang F, Zhang PZ, Yang M. [Chemical Constituents from Periplaneta americana]. Zhong Yao Cai. 2015 Oct;38(10):2038-41. Chinese. PubMed PMID: 27254913.
2: Ferreira CR, Cusmano-Ozog K. Spurious Elevation of Multiple Urine Amino Acids by Ion-Exchange Chromatography in Patients with Prolidase Deficiency. JIMD Rep. 2017;31:45-49. doi: 10.1007/8904_2016_552. Epub 2016 Apr 12. PubMed PMID: 27067078; PubMed Central PMCID: PMC5388643.
3: De Marco R, Di Gioia ML, Leggio A, Liguori A, Perri F, Siciliano C, Viscomi MC. A new non-natural arginine-like amino acid derivative with a sulfamoyl group in the side-chain. Amino Acids. 2010 Mar;38(3):691-700. doi: 10.1007/s00726-009-0267-2. Epub 2009 Mar 13. PubMed PMID: 19283444.
4: Sakurai M, Higashida S, Sugano M, Nishi T, Saito F, Ohata Y, Handa H, Komai T, Yagi R, Nishigaki T, et al. Studies of HIV-1 protease inhibitors. II. Incorporation of four types of hydroxyethylene dipeptide isosteres at the scissile site of substrate sequences. Chem Pharm Bull (Tokyo). 1993 Aug;41(8):1378-86. PubMed PMID: 8403086.
5: Ott H, Frey AJ, Hofmann A. The stereospecific cyclolization of n-(alpha-hydroxyacyl)-phenylalanyl-proline lactams. Tetrahedron. 1963 Nov;19(11):1675-84. PubMed PMID: 5879254.
6: Belshaw PJ, Walsh CT, Stachelhaus T. Aminoacyl-CoAs as probes of condensation domain selectivity in nonribosomal peptide synthesis. Science. 1999 Apr 16;284(5413):486-9. PubMed PMID: 10205056.
7: Gurunath R, Balaram P. Incorporation of a potentially helix breaking D-Phe-Pro sequence into the center of a right handed 16 residue peptide helix. Biochem Biophys Res Commun. 1994 Jul 15;202(1):241-5. PubMed PMID: 8037717.
8: Schoetz G, Trapp O, Schurig V. Determination of the cis-trans isomerization barrier of several L-peptidyl-L-proline dipeptides by dynamic capillary electrophoresis and computer simulation. Electrophoresis. 2001 Aug;22(12):2409-15. PubMed PMID: 11519944.
9: Hu M, Chen J, Tran D, Zhu Y, Leonardo G. The Caco-2 cell monolayers as an intestinal metabolism model: metabolism of dipeptide Phe-Pro. J Drug Target. 1994;2(1):79-89. PubMed PMID: 8069586.
10: Heymann E, Mentlein R, Nausch I, Erlanson-Albertsson C, Yoshimoto T, Feller AC. Processing of pro-colipase and trypsinogen by pancreatic dipeptidyl peptidase IV. Biomed Biochim Acta. 1986;45(5):575-84. PubMed PMID: 2875713.
11: Rathore AS, Horváth C. Capillary zone electrophoresis of interconverting cis-trans conformers of peptidyl-proline dipeptides: estimation of the kinetic parameters. Electrophoresis. 1997 Dec;18(15):2935-43. PubMed PMID: 9504833.
12: Sidorowicz W, Canizaro PC, Bĕhal FJ. Kinin cleavage by human erythrocytes. Am J Hematol. 1984;17(4):383-91. PubMed PMID: 6437213.