BIOPEP-UWM: Report

ID 433
Name Bitter peptide
sequence
YQQPVLGPVRGPFPIIV
Function:
Bitter peptide identified in Gouda cheese (source: beta-casein). Q value (i. e. average amount of free energy needed to transfer amino acid chains from ethanol to water) = 7376.5 J / (Mol x Res.).
 
Number of residues
17
Activity code
bi
Activity :
bitter
Chemical mass 1880.2303 Monoisotopic mass 1879.0687
EC50 :
0.00 µM


Bibliographic data:
Authors
Lemieux L., Simard R. E.
Title
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, 1992
Year Source
1992 book


Additional information:
BIOPEP database of sensory peptides and amino acids


SMILES: N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N1CCC[C@@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N1CCC[C@@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N1CCC[C@@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCC[C@@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C(C)C)C(=O)

InChI=1S/C91H142N22O21/c1-13-52(11)74(87(130)109-75(53(12)14-2)86(129)107-73(51(9)10)90(133)134)108-83(126)66-29-22-42-113(66)89(132)62(45-54-23-16-15-17-24-54)104-80(123)63-26-19-39-110(63)69(117)46-98-77(120)58(25-18-38-97-91(95)96)101-84(127)71(49(5)6)105-81(124)64-27-20-40-111(64)70(118)47-99-78(121)61(43-48(3)4)103-85(128)72(50(7)8)106-82(125)65-28-21-41-112(65)88(131)60(35-37-68(94)116)102-79(122)59(34-36-67(93)115)100-76(119)57(92)44-55-30-32-56(114)33-31-55/h15-17,23-24,30-33,48-53,57-66,71-75,114H,13-14,18-22,25-29,34-47,92H2,1-12H3,(H2,93,115)(H2,94,116)(H,98,120)(H,99,121)(H,100,119)(H,101,127)(H,102,122)(H,103,128)(H,104,123)(H,105,124)(H,106,125)(H,107,129)(H,108,126)(H,109,130)(H,133,134)(H4,95,96,97)/t52-,53-,57-,58-,59-,60-,61-,62-,63+,64+,65+,66+,71-,72-,73-,74-,75-/m0/s1

InChIKey: IWLAVRALCQDBEB-KCBMHBDKSA-N


Previous reference concerning peptide:

Visser S., Slangen C. J., Hup G., Exterkate F. A., Stadhouders J., 1983, The bitter flavour deffect in cheese; some chemical and microbiological aspects. Neth. Milk Dairy J., 37, 250-251

Immunomodulating peptide according to the BIOPEP database of bioactive peptides
Inhibitor of Angiotensin-converting enzyme (EC 3.4.15.1; MEROPS ID: XM02-001) according to the AHTPDB database


Database reference:
AHTPDB: ID 1163; 3381; 3602; 3678; 4089

BIOPEP database of bioactive peptides: ID 3059

SATPdb: ID satpdb18146