BIOPEP-UWM: Report

ID 32
Name bitter peptide
sequence
GY

Function:
(Rcaf) 0.33
 
Number of residues
2
Activity code
bi
Activity :
bitter
Chemical mass 238.2393 Monoisotopic mass 238.0950
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:
BIOPEP database of sensory peptides and amino acids


SMILES: c1cc(ccc1C[C@@H](C(=O)O)NC(=O)CN)O

InChI=1S/C11H14N2O4/c12-6-10(15)13-9(11(16)17)5-7-1-3-8(14)4-2-7/h1-4,9,14H,5-6,12H2,(H,13,15)(H,16,17)/t9-/m0/s1

InChIKey: XBGGUPMXALFZOT-VIFPVBQESA-N


Another references concerning bitter taste:

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

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


Inhibitor of Dipeptidyl Peptidase IV (EC 3.4.14.5) (MEROPS ID: S09.003) according to BIOPEP database of bioactive peptides
Inhibitor of tripeptidyl-peptidase II (EC 3.4.14.10) (MEROPS ID: S08.090) according to BRENDA database
Inhibitor of Angiotensin-Converting Enzyme (ACE) (EC 3.4.15.1) (MEROPS ID: M02.006) according to AHTPDB database; BIOPEP database of bioactive peptides; BRENDA database; ChEMBL database; PubChem database
Inhibitor of carboxypeptidase A (EC 3.4.17.1) (MEROPS ID: M14.001) according to BRENDA database


Isolated from sake and sake byproducts
Saito Y., Wanezaki K., Kawato A., Imayasu S., 1994, Antihypertensive effects of peptide in sake and its by-products on spontaneously antihypertensive rats. Biosci. Biotech. Biochem., 58, 812-816

Isolated from silk fibroin hydrolysate.
Zhou F., Xue Z., Wang J., 2010, Antihypertensive effects of silk fibroin hydrolysate by alcalase and purification of an ACE inhibitory dipeptide. J. Agric. Food Chem., 58, 6735-6740

Found in amaranth (Amarantus hypochondriacus) 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



Database reference:
AHTPDB: ID 1110; 1140; 1270; 1372; 1380; 1400; 1419; 1809; 1891; 2653; 2746; 2790; 2934; 2980; 3101; 3301; 3496; 3843; 3938; 4075; 4230; 4250; 4251; 4440; 4497; 4682; 5153; 5430; 5591; 5740; 6210; 6450

BIOPEP database of bioactive peptides: ID 3532; 8788

BRENDA: Ligand Gly-Tyr

ChEBI: ID 73517

ChEMBL: ID CHEMBL53400

ChemSpider ID: 83798

EROP-Moscow: ID E09245

PubChem: ID 92829

ZINC: ID ZINC01730678