BIOPEP-UWM: Report

ID 386
Name Bitter peptide
sequence
YQQPVLGPVRGPFPII
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) = 7395.4 J / (Mol x Res,)=1766,9 cal/mol.
 
Number of residues
16
Activity code
bi
Activity :
bitter
Chemical mass 1781.0996 Monoisotopic mass 1780.0005
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 Journal


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)O

InChI=1S/C86H133N21O20/c1-11-49(9)70(82(123)103-71(85(126)127)50(10)12-2)102-79(120)63-27-20-40-107(63)84(125)59(43-51-21-14-13-15-22-51)99-76(117)60-24-17-37-104(60)66(111)44-93-73(114)55(23-16-36-92-86(90)91)96-80(121)68(47(5)6)100-77(118)61-25-18-38-105(61)67(112)45-94-74(115)58(41-46(3)4)98-81(122)69(48(7)8)101-78(119)62-26-19-39-106(62)83(124)57(33-35-65(89)110)97-75(116)56(32-34-64(88)109)95-72(113)54(87)42-52-28-30-53(108)31-29-52/h13-15,21-22,28-31,46-50,54-63,68-71,108H,11-12,16-20,23-27,32-45,87H2,1-10H3,(H2,88,109)(H2,89,110)(H,93,114)(H,94,115)(H,95,113)(H,96,121)(H,97,116)(H,98,122)(H,99,117)(H,100,118)(H,101,119)(H,102,120)(H,103,123)(H,126,127)(H4,90,91,92)/t49-,50-,54-,55-,56-,57-,58-,59-,60+,61+,62+,63+,68-,69-,70-,71-/m0/s1

InChIKey: NNPOSJZYXZBSHT-CHSJHOFDSA-N


Previous references concerning peptide:

Visser S., Slangen C. J., Hup G., Stadhouders J., 1983, Bitter flavors in cheese. 3. Comparative gel-chromatographic analysis on hydrophobic peptide fractions from twelve Gouda type-cheeses and identification of bitter peptides isolated from a cheese made from Streptococcus cremoris strain HP. Neth. Milk Dairy J., 37, 181-192

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


Database reference: