BIOPEP-UWM: Report

ID 52
Name bitter peptide
sequence
LF

Function:
(Rcaf) 0.77
 
Number of residues
2
Activity code
bi
Activity :
bitter
Chemical mass 278.3459 Monoisotopic mass 278.1625
EC50 :
0.00 µM



Bibliographic data:
Authors
Ishibashi N., Sadamori K., Yamamoto O., Kanehisa H., Kouge K., Kikuchi E., Okai H., Fukui S.
Title
Bitterness of phenylalanine- and tyrosine-containing peptides. Agric. Biol. Chem., 51, 3309-3313, 1987
Year Source
1987 Journal



Additional information:
Additional information:

BIOPEP database of sensory peptides and amino acids


SMILES: N[C@H](C(=O)N[C@H](C(=O)O)Cc1ccccc1)CC(C)C

InChI=1S/C15H22N2O3/c1-10(2)8-12(16)14(18)17-13(15(19)20)9-11-6-4-3-5-7-11/h3-7,10,12-13H,8-9,16H2,1-2H3,(H,17,18)(H,19,20)/t12-,13-/m0/s1

InChIKey: KFKWRHQBZQICHA-STQMWFEESA-N


Another references concerning bitterness:

Asao M., Iwamura H., Akamatsu M., Fujita T., 1987, Quantitative structure-activity relationships of the bitter thresholds of amino acids, peptides, and their derivatives. J. Med. Chem., 30, 1873-1879

Lemieux L., Simard R. E., 1992, Bitter flavour in dairy products. II. A review of bitter peptides from caseins: their formation, isolation and identification, structure masking and inhibition. Lait, 72, 335-382

Collantes E. R., Dunn W. J., 1995, Amino acid side chain descriptors for quantitative structure-activity relationship studies of peptide analogues. J. Med. Chem., 38, 2705-2713


alpha/beta-lactokinin [alpha-La (52-53); beta-Lg (104-105)]
Meisel H., 1998, Overview on milk protein-derived peptides. Int. Dairy J., 8, 363-373

Found in salmon protein hydrolysate.
Ono S., Hosokawa M., Miyashita K., Takahashi K., 2006, Inhibiton properties of dipeptides from salmon muscle hydrolysate on angiotensin I-converting enzyme. Int. J. Food Sci. Technol., 41, 383-387

Found in amaranth proteins: Barba de la Rosa A. P., Barba Montoya A., Martínez-Cuevas P., Hernández-Ledesma B., León-Galván M. F., De León-Rodríguez A., González C., 2010, Tryptic amaranth glutelin digests induce endothelial nitric oxide production through inhibition of ACE: antihypertensive role of amaranth peptides. Nitric Oxide, 23, 106-111

Inhibitor of Angiotensin-Converting Enzyme (ACE) (EC 3.4.15.1) (MEROPS ID: XM02-001) according to AHTPDB database; BIOPEP database of bioactive peptides; BRENDA database
Inhibitor of Carboxypeptidase C (EC 3.4.16.5) (MEROPS ID S10.004) according to BRENDA database
Inhibitor of Pseudolysin (EC 3.4.24.26) (MEROPS ID M04.005) according to BRENDA database



Database reference:
AHTPDB: ID 1161; 1330; 1388; 1415; 1432; 1675; 2687; 3165; 3209; 3302; 3514; 3600; 3854; 3976; 4086; 4473; 5454; 5602; 5711; 5777; 6466

BIOPEP database of bioactive peptides: ID 3551

BRENDA: Ligand Leu-Phe

ChEBI: ID 73585

ChEMBL: ID CHEMBL54936

ChemSpider: ID 5360450

EROP-Moscow: ID E01831

Metabolomics Workbench: ID ME015586

PubChem: ID 6992310

SATPdb: ID satpdb28695

ZINC: ID ZINC01569745