Peptide properties

1Top 2Function-activity relationship 3Calculated physicochemical properties 4Peptide source & Food-borne protein(s) search 5Biological/Functional activity & target protein 6Taste properties & Structure 7Preparation method 8Stability & Cytotoxicity 9Additional information 10Database cross-references 11Reference(s)

List of peptide properties

DFBP ID - DFBPOPIO0065(Opioid peptide)

DFBP ID	DFBPOPIO0065
Peptide sequence	GYYP
Type	Native peptide
Peptide/Function name	Opioid peptide, Gluten exorphin A4

Function-activity relationship

Main bioactivity	Opioid activity
Otheir bioactivity	N.D

Calculated physicochemical properties

Three-letter amino acid

Gly-Tyr-Tyr-Pro

Single-letter amino acid

GYYP

Peptide length

Peptide mass

Experimental mass	Theoretical mass
N.D	498.53 Da ^c

Net charge

0.00 ^c

Isoelectric point (pI)

5.87 ^c

IC₅₀

N.D

pIC₅₀

N.D

GRAVY

-1.1500^c

Hydrophilic residue ratio

50%^c

Peptide calculator

Peptide source & Food-borne protein(s) search

Classification	Plant
Organism/Source	Wheat
Precursor protein	Wheat gluten
Residue position	f(305-308, ...)
Precursor protein(s) search	Source.1: DFBPPR1128 ---- Plant proteins ---- Polyamine oxidase 4 Source.2: DFBPPR5095 ---- Plant proteins ---- Superoxide dismutase [Fe], chloroplastic Source.3: DFBPPR6683 ---- Plant proteins ---- Glutenin, high molecular weight subunit DX5 Source.4: DFBPPR6852 ---- Plant proteins ---- Glutenin, high molecular weight subunit DY10 Source.5: DFBPPR6872 ---- Plant proteins ---- Glutenin, high molecular weight subunit 12 Source.6: DFBPPR6886 ---- Plant proteins ---- Glutenin, high molecular weight subunit PW212 Source.7: DFBPPR6924 ---- Plant proteins ---- Glutenin, high molecular weight subunit PC256 Source.8: DFBPPR16581 ---- Animal proteins ---- NADH-ubiquinone oxidoreductase chain 5 Source.9: DFBPPR18389 ---- Animal proteins ---- Short transient receptor potential channel 6 Source.10: DFBPPR19208 ---- Animal proteins ---- Sushi repeat-containing protein SRPX2 Source.11: DFBPPR19999 ---- Animal proteins ---- Cell death-inducing p53-target protein 1 Source.12: DFBPPR20230 ---- Animal proteins ---- RNA 3'-terminal phosphate cyclase Source.13: DFBPPR22090 ---- Animal proteins ---- 5'-nucleotidase domain-containing protein 1 Source.14: DFBPPR9313 ---- Animal proteins ---- SRSF protein kinase 3 Source.15: DFBPPR9634 ---- Animal proteins ---- NADH-ubiquinone oxidoreductase chain 5 Source.16: DFBPPR10218 ---- Animal proteins ---- Occludin Source.17: DFBPPR11063 ---- Animal proteins ---- Leukocyte cell-derived chemotaxin 1 Source.18: DFBPPR11912 ---- Animal proteins ---- Homeobox protein Hox-A13 Source.19: DFBPPR11961 ---- Animal proteins ---- KIF-binding protein Source.20: DFBPPR12595 ---- Animal proteins ---- Hyaluronidase PH-20 Source.21: DFBPPR13366 ---- Animal proteins ---- NADH-ubiquinone oxidoreductase chain 5 Source.22: DFBPPR13883 ---- Animal proteins ---- NADH-ubiquinone oxidoreductase chain 5 Source.23: DFBPPR8158 ---- Plant protein ---- Glycine-rich cell wall structural protein 1.0
Link-research Inductive analysis	There are no literature reports on the discovery of this sequence in other food-source proteins.

Biological/Functional activity & target protein

Opioid activity

Together with the results of radioreceptor assays, it is suggested that gluten exorphin A4 is δ-selective ligands, this peptide had no affinity for κ-receptors. As shown in the table 1.

Table 1 Opioid activities and receptor affinities and yields of opioid peptides in the pepsin-pancreatic elastase and the pepsin-thermolysin digests
Peptides	Receptor affinities (IC₅₀)		μ/δ	Opioid activities (IC₅₀)		μ/δ	Yields from the digests^[1]
	[³H]DAGO	[³H]DADLE		GPI	MVD		Pepsin-elastase (μg/g)	Pepsin-thermolysin (μg/g)
	μ (μM)	δ (μM)		μ (μM)	δ (μM)		Pepsin-elastase (μg/g)	Pepsin-thermolysin (μg/g)
GYYPTS	1000	5.0	202	> 1000	72	－	－	－
GYYPT	700	1.5	467	1000	60	16.7	250	40
GYYP	> 1000	3.8	－	> 1000	70	－	(a)	400
RYYP	(a)	(a)	－	> 1000	190	－	－	－
SYYP	> 1000	5.6	－	> 1000	200	－	－	－
WYYP	700	100	7	(a)	(b)	－	－	－
YYPT	(a)	(a)	－	(a)	800	－	500	(a)
YYP	> 1000	100	－	> 1000	1000	－	－	－
GYY	> 1000	500	－	> 1000	1000	－	－	－
YGGWL	0.045	0.005	9	0.05	0.017	2.9	0.1	0.1
YGGW	0.17	0.18	0.94	1.5	3.4	0.44	3.0	3.0
YGGFL	0.037	0.003	12.3	0.04	0.004	10	－	－

(a), not determined; (b), this peptide displayed opioid antagonist activity on the MVD assay. (pA₂ value = 3.3)

Specific target protein(s)

Specific Target Protein(s):
Delta-type opioid receptor

Taste properties & Structure

Bitterness

Literature report	N.D
Bitter prediction tools	Bitter taste ^prediction

SMILES

NCC(=O)N[C@@]([H])(Cc1ccc(O)cc1)C(=O)N[C@@]([H])(Cc1ccc(O)cc1)C(=O)N1[C@@]([H])(CCC1)C(=O)O

Preparation method

Mode of preparation	Enzymatic hydrolysis
Enzyme(s)/starter culture	Wheat gluten was digested with pepsin-thermolysin. Wheat gluten was digested with pepsin-pancreatic elastase^[1].

Stability & Cytotoxicity

Peptide stability

Literature report:	N.D
EHP-Tool:	Enzymatic Hydrolysis Prediction Tool (EHP-Tool)

Peptide cytotoxicity

Literature report:	N.D
Prediction:	ToxinPred

Additional information

N.D

Database cross-references

[D1]

[D2]

[D3]

[D4]

Reference(s)

Primary literature	Fukudome S, Yoshikawa M. Opioid peptides derived from wheat gluten: their isolation and characterization. FEBS Lett. 1992 Jan 13;296(1):107-11. PMID: 1309704 DOI: 10.1016/0014-5793(92)80414-c
Other literature(s)	[1] Fukudome S I, Jinsmaa Y, Matsukawa T, et al. Release of opioid peptides, gluten exorphins by the action of pancreatic elastase[J]. Febs Letters, 1997, 412(3):475-9.
PubDate	1992