58569-55-4

Basic information

• Product Name: H-TYR-GLY-GLY-PHE-MET-OH
• Synonyms: porcine,beta-endorphin1-5;[Met5]Enkephalin acetate salt hydrate;methionine enkephalin acetate;N-[N-[N-(N-L-tyrosylglycyl)glycyl]-L-phenylalanyl]-L-methionine;(methionine5)enkephalin;[5-Methionin]Enkephalin, Enkephalin M;[Met5]Enkephalin hydrate acetate salt;TYR-GLY-GLY-PHE-MET H2O
• CAS NO: 58569-55-4
• Molecular Formula: C27H35N5O7S
• Molecular Weight: 573.66
• EINECS: 261-335-8
• Product Categories: Peptide;Opioid receptor and opioid-like receptor;Pepetides;peptides
• Mol File: 58569-55-4.mol
• Article Data: 24

Chemical Properties

• Melting Point: 174-177 °C
• Boiling Point: 1052.9 °C at 760 mmHg
• Flash Point: 590.6 °C
• Appearance: white/powder
• Density: 1.324 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated), Water (Slightly)
• PKA: 3.23±0.10(Predicted)
• Stability: Unstable in alkaline solution
• CAS DataBase Reference: H-TYR-GLY-GLY-PHE-MET-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-TYR-GLY-GLY-PHE-MET-OH(58569-55-4)
• EPA Substance Registry System: H-TYR-GLY-GLY-PHE-MET-OH(58569-55-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 58569-55-4(Hazardous Substances Data)

Usage

Uses

Endogenous opioid peptide that also functions as a growth factor on many cell types at a receptor that is distinct from the neuronal opioid receptors

InChI:InChI=1/C27H35N5O7S/c1-40-12-11-21(27(38)39)32-26(37)22(14-17-5-3-2-4-6-17)31-24(35)16-29-23(34)15-30-25(36)20(28)13-18-7-9-19(33)10-8-18/h2-10,20-22,33H,11-16,28H2,1H3,(H,29,34)(H,30,36)(H,31,35)(H,32,37)(H,38,39)/t20-,21-,22-/m0/s1

Synthetic route

(S)-2-{(S)-2-[2-(2-{(S)-3-[4-(4-Bromo-phenoxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionylamino}-acetylamino)-acetylamino]-3-phenyl-propionylamino}-4-methanesulfinyl-butyric acid → met-enkephalin (58569-55-4)

Conditions	Yield
With p-cresol; dimethylsulfide; hydrogen fluoride at 0℃; for 1h;	92%

boc-Tyr-Gly-Gly-Phe-Met-OH (59481-77-5) → met-enkephalin (58569-55-4)

Conditions	Yield
With hydrogenchloride; acetic acid for 1h;	90%
With hydrogenchloride In acetic acid for 0.5h;	85%

Boc-Tyr-Gly-Gly-Phe-Met-OBut (82362-16-1) → met-enkephalin (58569-55-4)

Conditions	Yield
With methyl-phenyl-thioether; trifluoroacetic acid for 1h; Ambient temperature;	74%

C17H13NO10S2(2-)*2Na(1+) + C20H19NO10S3(2-)*2Na(1+) + C24H19NO10S2(2-)*2Na(1+) + C24H19NO11S2(2-)*2Na(1+) → met-enkephalin (58569-55-4)

Conditions	Yield
Stage #1: C20H19NO10S3(2-)*2Na(1+) With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethyl cyanoglyoxylate-2-oxime In water; acetonitrile at 20℃; for 0.75h; Stage #2: With ethanolamine In water for 0.166667h; Stage #3: C17H13NO10S2(2-)*2Na(1+); C24H19NO10S2(2-)*2Na(1+); C24H19NO11S2(2-)*2Na(1+) Further stages;	63%

Boc-Tyr(Mtb)-Gly-Gly-Phe-Met-OMtb (129398-74-9) → met-enkephalin (58569-55-4)

Conditions	Yield
With 3,5-dimethylmethoxybenzene; ethane-1,2-dithiol; trifluoroacetic acid 1) 0 deg C, 120 min, 2) 20 deg C, 60 min;	57%

Boc-Tyr(Cl2Bzl)-Gly-Gly-Phe-Met-OBzl (129398-68-1) → met-enkephalin (58569-55-4)

Conditions	Yield
With trifluorormethanesulfonic acid; methyl-phenyl-thioether; ethane-1,2-dithiol; 3-methyl-phenol; trifluoroacetic acid at 0℃; for 1.5h;	49%

N-(diphenylphosphinoyl)tyrosylglycylglycylphenylalanylmethionine (148715-90-6) → met-enkephalin (58569-55-4)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 6h;	40%

Boc-Tyr(tert.-Bu)-Gly-Gly-Phe-Met (62530-43-2) → met-enkephalin (58569-55-4)

Conditions	Yield
With hydrogenchloride; ethane-1,2-dithiol; methoxybenzene In 1,4-dioxane for 1h; Ambient temperature; Yield given;

Z-Tyr(Bzl)-Gly-Gly-Phe-Met (74937-32-9) → met-enkephalin (58569-55-4)

Conditions	Yield
With methyl-phenyl-thioether In trifluoroacetic acid at 25℃; for 4h; Yield given;

methyl ester of N,O-di-t-butyloxycarbonyl-L-tyrosylglycylglycyl-L-phenylalanyl-L-methionine (81649-52-7) → met-enkephalin (58569-55-4)

Conditions	Yield
With hydrogenchloride; sodium hydroxide 1.) methanol, water, 4 h, 2.) AcOH, 45 min; Yield given. Multistep reaction;

Z-Tyr-Gly-Gly-Phe-Hcy(Bzl)-OBzl (97512-82-8) + methyl iodide (74-88-4) → met-enkephalin (58569-55-4)

Conditions	Yield
With sodium 1.) NH3 liq., -70 deg C, 2.) hexane-NH3, -70 -> -25 deg C, 1 h; Yield given. Multistep reaction;

methionine-enkephalin sulfoxide (60283-51-4) → met-enkephalin (58569-55-4)

Conditions	Yield
With ammonium iodide; dimethylsulfide In trifluoroacetic acid at 0℃;

BocMet-R, Boc-amino acids → met-enkephalin (58569-55-4)

Conditions	Yield
Yield given; Multistep reaction;

phospho-Tyr-Gly-Gly-Phe-Met-OH → met-enkephalin (58569-55-4) + O-phosphono-L-tyrosine (21820-51-9) + L-tyrosine (60-18-4) + [des-tyr1]-methionine enkephalin (61370-88-5)

Conditions	Yield
With aminopeptidase M (EC3.4.11.2); 2-amino-2-hydroxymethyl-1,3-propanediol at 37℃; for 1h; pH=7.02; Kinetics; Hydrolysis;

-enkephalyl-arg6-phe7 → L-arginyl-L-phenylalanine (2047-13-4) + met-enkephalin (58569-55-4)

Conditions	Yield
With angiotensin I converting enzyme In various solvent(s) at 37℃; pH=7.75; Kinetics;

-enkephalyl-arg6-phe7 → YG (673-08-5) + met-enkephalin (58569-55-4) + tyrosylglycylglycine (21778-69-8) + L-tyrosine (60-18-4)

Conditions	Yield
With membrane fraction In various solvents at 37℃; for 1h; pH=7.4; Product distribution; Further Variations:; Reagents;

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + Boc-Pro, Boc-Cys(Bzl), Boc-Asn NPE, Boc-Val → met-enkephalin (58569-55-4)

Conditions

Yield

Multi-step reaction with 8 steps 1: NMM / dimethylformamide / 0.17 h / -15 °C 2: NMM / dimethylformamide / 20 h / -20 °C 3: 90 percent / 1.5 N HCl/AcOH 4: 97 percent / HOBt*H2O, NEt3 / dimethylformamide / 23 h 5: 95 percent / 1.5 N HCl/AcOH / 1 h 6: 90 percent / HOBt*H2O, NEt3, DCC / dimethylformamide / a) -5 deg C to 0 deg C, 1 h, b) 20 deg C, 24 h 7: 86 percent / 0.5 M NaOH / acetone / 1.5 h 8: 90 percent / 1.3 M HCl/AcOH / 1 h View Scheme

Methyl ester of N-t-butyloxycarbonyl-L-phenylalanyl-L-methionine (40290-63-9) → met-enkephalin (58569-55-4)

Conditions	Yield
Multi-step reaction with 6 steps 1: 90 percent / 1.5 N HCl/AcOH 2: 97 percent / HOBt*H2O, NEt3 / dimethylformamide / 23 h 3: 95 percent / 1.5 N HCl/AcOH / 1 h 4: 90 percent / HOBt*H2O, NEt3, DCC / dimethylformamide / a) -5 deg C to 0 deg C, 1 h, b) 20 deg C, 24 h 5: 86 percent / 0.5 M NaOH / acetone / 1.5 h 6: 90 percent / 1.3 M HCl/AcOH / 1 h View Scheme
Multi-step reaction with 5 steps 1: 98 percent / 4 M HCl / dioxane / 0.75 h 2: 1.) NH3, 2.) AcOH / 1.) CHCl3, 5 min, 2.) THF, 24 h 3: 91 percent / 2 M HCl / acetic acid / 0.75 h 4: 1.) NH3, 2.) AcOH / 1.) CHCl3, 5 min, 2.) DMF, THF, 24 h 5: 1.) 2 M NaOH, 2.) 2M HCl / 1.) methanol, water, 4 h, 2.) AcOH, 45 min View Scheme
Multi-step reaction with 8 steps 1: 1.) HCO2H, PhOMe, HS-(CH2)2-SH, 2.) HCl / 1.) room temp., 5 h, 2.) Et2O 2: 1) N-methylmorpholine, 1-β-naphthalenesulphonyloxybenzotriazole / 1) EtOAc, DMF, 1.5h 2) RT 12h 3: 1.) HCO2H, PhOMe, HS-(CH2)2-SH, 2.) HCl 4: 1) N-methylmorpholine, 1-β-naphthalenesulphonyloxybenzotriazole / 1) EtOAc, DMF, 1.5h, 2) RT, 12h 5: 1.) HCO2H, PhOMe, HS-(CH2)2-SH, 2.) HCl 6: 1) 1-β-naphthalenesulphonyloxybenzotriazole, 2) N-methylmorpholine / 1) EtOAc, 1.5h, DMF, RT, 2) RT, 15h 7: 92.23 percent / 2N NaOH / methanol; H2O / 1 h / Ambient temperature 8: 10percentHCl, C6H5OCH3, HS-(CH2)2-SH / dioxane / 1 h / Ambient temperature View Scheme

methyl N-tert-butoxycarbonyl-L-tyrosyldiglycyl-L-phenylalanyl-L-methioninate (60566-44-1) → met-enkephalin (58569-55-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / 0.5 M NaOH / acetone / 1.5 h 2: 90 percent / 1.3 M HCl/AcOH / 1 h View Scheme

N-tert-Butyloxycarbonyl-glycyl-glycyl-L-phenylalanyl-L-methionin-methylester (70035-45-9) → met-enkephalin (58569-55-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / 1.5 N HCl/AcOH / 1 h 2: 90 percent / HOBt*H2O, NEt3, DCC / dimethylformamide / a) -5 deg C to 0 deg C, 1 h, b) 20 deg C, 24 h 3: 86 percent / 0.5 M NaOH / acetone / 1.5 h 4: 90 percent / 1.3 M HCl/AcOH / 1 h View Scheme
Multi-step reaction with 3 steps 1: 91 percent / 2 M HCl / acetic acid / 0.75 h 2: 1.) NH3, 2.) AcOH / 1.) CHCl3, 5 min, 2.) DMF, THF, 24 h 3: 1.) 2 M NaOH, 2.) 2M HCl / 1.) methanol, water, 4 h, 2.) AcOH, 45 min View Scheme
Multi-step reaction with 4 steps 1: 1.) HCO2H, PhOMe, HS-(CH2)2-SH, 2.) HCl 2: 1) 1-β-naphthalenesulphonyloxybenzotriazole, 2) N-methylmorpholine / 1) EtOAc, 1.5h, DMF, RT, 2) RT, 15h 3: 92.23 percent / 2N NaOH / methanol; H2O / 1 h / Ambient temperature 4: 10percentHCl, C6H5OCH3, HS-(CH2)2-SH / dioxane / 1 h / Ambient temperature View Scheme

Boc-Phe-O-COO-isoBu (67729-36-6, 60398-40-5) → met-enkephalin (58569-55-4)

Conditions

Yield

Multi-step reaction with 7 steps 1: NMM / dimethylformamide / 20 h / -20 °C 2: 90 percent / 1.5 N HCl/AcOH 3: 97 percent / HOBt*H2O, NEt3 / dimethylformamide / 23 h 4: 95 percent / 1.5 N HCl/AcOH / 1 h 5: 90 percent / HOBt*H2O, NEt3, DCC / dimethylformamide / a) -5 deg C to 0 deg C, 1 h, b) 20 deg C, 24 h 6: 86 percent / 0.5 M NaOH / acetone / 1.5 h 7: 90 percent / 1.3 M HCl/AcOH / 1 h View Scheme

hydrochloride of methyl ester of glycylglycyl-L-phenylalanyl-L-methionine (70035-46-0) → met-enkephalin (58569-55-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / HOBt*H2O, NEt3, DCC / dimethylformamide / a) -5 deg C to 0 deg C, 1 h, b) 20 deg C, 24 h 2: 86 percent / 0.5 M NaOH / acetone / 1.5 h 3: 90 percent / 1.3 M HCl/AcOH / 1 h View Scheme
Multi-step reaction with 2 steps 1: 1.) NH3, 2.) AcOH / 1.) CHCl3, 5 min, 2.) DMF, THF, 24 h 2: 1.) 2 M NaOH, 2.) 2M HCl / 1.) methanol, water, 4 h, 2.) AcOH, 45 min View Scheme
Multi-step reaction with 3 steps 1: N-methylmorpholine, 2,6-luditine / CH2Cl2; dimethylformamide / 1.) 0 deg C, 1 h, 2.) r. t., 1 h 2: 91 percent / aq. NaOH / dimethylformamide / 6 h 3: 40 percent / aq. HCl / dioxane / 6 h View Scheme
Multi-step reaction with 3 steps 1: 1) 1-β-naphthalenesulphonyloxybenzotriazole, 2) N-methylmorpholine / 1) EtOAc, 1.5h, DMF, RT, 2) RT, 15h 2: 92.23 percent / 2N NaOH / methanol; H2O / 1 h / Ambient temperature 3: 10percentHCl, C6H5OCH3, HS-(CH2)2-SH / dioxane / 1 h / Ambient temperature View Scheme

L-phenylalaninyl-L-methionine methyl ether p-toluenesulfonate → met-enkephalin (58569-55-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: 97 percent / HOBt*H2O, NEt3 / dimethylformamide / 23 h 2: 95 percent / 1.5 N HCl/AcOH / 1 h 3: 90 percent / HOBt*H2O, NEt3, DCC / dimethylformamide / a) -5 deg C to 0 deg C, 1 h, b) 20 deg C, 24 h 4: 86 percent / 0.5 M NaOH / acetone / 1.5 h 5: 90 percent / 1.3 M HCl/AcOH / 1 h View Scheme

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → met-enkephalin (58569-55-4)

Conditions	Yield
Multi-step reaction with 7 steps 1: 90 percent / N,N'-dicyclohexylcarbodiimide (DCCI) / tetrahydrofuran / Ambient temperature 2: 1.) NH3, 2.) AcOH / 1.) CHCl3, 5 min, 2.) THF, 24 h 3: 98 percent / 4 M HCl / dioxane / 0.75 h 4: 1.) NH3, 2.) AcOH / 1.) CHCl3, 5 min, 2.) THF, 24 h 5: 91 percent / 2 M HCl / acetic acid / 0.75 h 6: 1.) NH3, 2.) AcOH / 1.) CHCl3, 5 min, 2.) DMF, THF, 24 h 7: 1.) 2 M NaOH, 2.) 2M HCl / 1.) methanol, water, 4 h, 2.) AcOH, 45 min View Scheme
Multi-step reaction with 4 steps 1: 1.) N-methylmorpholine, isobutyl chloroformate / 1.) THF, -15 deg C, 1 min, 2.) -10 deg C, 30 min; 20 deg C, 2 h 2: 95 percent / 4.1 M HCl / dioxane / 4 h / 20 °C 3: 1.) 4.1 M HCl, isopentyl nitrite, 2.) Et3N / 1.) DMF, -20 deg C, 1 h, 2.) -30 deg C, 1 h; 4 deg C, 21 h 4: 1.) Na / 1.) NH3 liq., -70 deg C, 2.) hexane-NH3, -70 -> -25 deg C, 1 h View Scheme
Multi-step reaction with 9 steps 1: 1)N-methylmorpholine, 1-β-napthalenesulphonyloxybenzotriazole / 1)EtOAc, RT, 1.5h 2) 12h RT 2: 1.) HCO2H, PhOMe, HS-(CH2)2-SH, 2.) HCl / 1.) room temp., 5 h, 2.) Et2O 3: 1) N-methylmorpholine, 1-β-naphthalenesulphonyloxybenzotriazole / 1) EtOAc, DMF, 1.5h 2) RT 12h 4: 1.) HCO2H, PhOMe, HS-(CH2)2-SH, 2.) HCl 5: 1) N-methylmorpholine, 1-β-naphthalenesulphonyloxybenzotriazole / 1) EtOAc, DMF, 1.5h, 2) RT, 12h 6: 1.) HCO2H, PhOMe, HS-(CH2)2-SH, 2.) HCl 7: 1) 1-β-naphthalenesulphonyloxybenzotriazole, 2) N-methylmorpholine / 1) EtOAc, 1.5h, DMF, RT, 2) RT, 15h 8: 92.23 percent / 2N NaOH / methanol; H2O / 1 h / Ambient temperature 9: 10percentHCl, C6H5OCH3, HS-(CH2)2-SH / dioxane / 1 h / Ambient temperature View Scheme
Multi-step reaction with 8 steps 1.1: N,N-dimethyl-formamide / 20 °C 2.1: 4-methyl-morpholine / N,N-dimethyl-formamide / 0 °C / pH 7 2.2: 4 h / 0 - 20 °C 3.1: hydrogenchloride; methyl-phenyl-thioether; 2-hydroxyethanethiol / 1,4-dioxane / 0.25 h / 20 °C 4.1: 4-methyl-morpholine / N,N-dimethyl-formamide / 0 °C / pH 7 4.2: 0 °C 4.3: 4 h / 0 - 20 °C 5.1: hydrogenchloride; methyl-phenyl-thioether; 2-hydroxyethanethiol / 1,4-dioxane / 1 h / 20 °C 6.1: 4-methyl-morpholine / N,N-dimethyl-formamide / 0 °C 6.3: 4 h / 0 - 20 °C 7.1: palladium 10% on activated carbon / methanol / 0.33 h / 20 °C 8.1: hydrogenchloride; methyl-phenyl-thioether; 2-hydroxyethanethiol / 1,4-dioxane / 0.5 h / 0 °C View Scheme

hydrochloride of methyl ester of L-phenylalanyl-L-methionine (40290-65-1) → met-enkephalin (58569-55-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) NH3, 2.) AcOH / 1.) CHCl3, 5 min, 2.) THF, 24 h 2: 91 percent / 2 M HCl / acetic acid / 0.75 h 3: 1.) NH3, 2.) AcOH / 1.) CHCl3, 5 min, 2.) DMF, THF, 24 h 4: 1.) 2 M NaOH, 2.) 2M HCl / 1.) methanol, water, 4 h, 2.) AcOH, 45 min View Scheme
Multi-step reaction with 7 steps 1: 1) N-methylmorpholine, 1-β-naphthalenesulphonyloxybenzotriazole / 1) EtOAc, DMF, 1.5h 2) RT 12h 2: 1.) HCO2H, PhOMe, HS-(CH2)2-SH, 2.) HCl 3: 1) N-methylmorpholine, 1-β-naphthalenesulphonyloxybenzotriazole / 1) EtOAc, DMF, 1.5h, 2) RT, 12h 4: 1.) HCO2H, PhOMe, HS-(CH2)2-SH, 2.) HCl 5: 1) 1-β-naphthalenesulphonyloxybenzotriazole, 2) N-methylmorpholine / 1) EtOAc, 1.5h, DMF, RT, 2) RT, 15h 6: 92.23 percent / 2N NaOH / methanol; H2O / 1 h / Ambient temperature 7: 10percentHCl, C6H5OCH3, HS-(CH2)2-SH / dioxane / 1 h / Ambient temperature View Scheme

O-(t-butyloxycarbonyl-L-phenylalanyl)-2-pyridylmethylketoxime (81638-94-0) → met-enkephalin (58569-55-4)

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) NH3, 2.) AcOH / 1.) CHCl3, 5 min, 2.) THF, 24 h 2: 98 percent / 4 M HCl / dioxane / 0.75 h 3: 1.) NH3, 2.) AcOH / 1.) CHCl3, 5 min, 2.) THF, 24 h 4: 91 percent / 2 M HCl / acetic acid / 0.75 h 5: 1.) NH3, 2.) AcOH / 1.) CHCl3, 5 min, 2.) DMF, THF, 24 h 6: 1.) 2 M NaOH, 2.) 2M HCl / 1.) methanol, water, 4 h, 2.) AcOH, 45 min View Scheme

N-benzyloxycarbonyl-O-benzyl-L-tyrosine (86827-18-1, 92455-53-3, 16677-29-5) → met-enkephalin (58569-55-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: dicyclohexylcarbodi-imide 4: thioanisole / trifluoroacetic acid / 4 h / 25 °C View Scheme

N-(O-benzyl-N-benzyloxycarbonyl-L-tyrosyl)-glycine ethyl ester (21869-36-3) → met-enkephalin (58569-55-4)

Conditions	Yield
Multi-step reaction with 3 steps 3: thioanisole / trifluoroacetic acid / 4 h / 25 °C View Scheme

Z-Tyr(Bzl)-Gly-N2H3 (74916-75-9) → met-enkephalin (58569-55-4)

Conditions	Yield
Multi-step reaction with 2 steps 2: thioanisole / trifluoroacetic acid / 4 h / 25 °C View Scheme

fluorescein isothiocyanate (3326-32-7, 27072-45-3) + met-enkephalin (58569-55-4) → C48H46N6O12S2

Conditions	Yield
With N-ethylmorpholine; In N,N-dimethyl-formamide at 20℃; for 24h;

Upstream product

• 1188307-69-8 C₄₁H₅₀N₆O₁₇S 
• 129398-68-1 Boc-Tyr(Cl₂Bzl)-Gly-Gly-Phe-Met-OBzl 
• 129398-74-9 Boc-Tyr(Mtb)-Gly-Gly-Phe-Met-OMtb 
• 60-18-4 L-tyrosine 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 63-91-2 L-phenylalanine 
• 63-68-3 L-methionine 
• 68739-90-2 L?methionine benzyl ester p?toluenesulfonate 
• 61543-22-4 Boc-Phe-Met-OBzl 
• 99532-43-1 BOC-Phe-POBT 
• 60283-51-4 methionine-enkephalin sulfoxide 
• 81649-52-7 methyl ester of N,O-di-t-butyloxycarbonyl-L-tyrosylglycylglycyl-L-phenylalanyl-L-methionine 

Downstream Products

• 60283-51-4 methionine-enkephalin sulfoxide 
• 60117-26-2 C₂₇H₃₅N₅O₈S 
• 75525-04-1 YGGFMYGGFM 
• 1334396-63-2 Ac-AAAYGGFM 
• 59481-77-5 boc-Tyr-Gly-Gly-Phe-Met-OH 

Relevant articles and documents

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Neutrophils play a major role in acute inflammation in part by generating superoxide and an array of other reactive species. These white blood cells also contribute to protection against inflammatory pain by releasing opioid peptides. The biochemical interactions of enkephalins with neutrophil-derived oxidants are not well understood. In this investigation we reveal that neutrophils use myeloperoxidase to oxidize enkephalins to their corresponding tyrosyl free radicals, which react preferentially with the superoxide to form a hydroperoxide. In methionine enkephalin, rapid intramolecular oxygen transfer from the hydroperoxide to the Met sulfur results in the formation of a sulfoxide derivative. This reaction may occur at sites of inflammation where enkephalins are released and neutrophils generate large amounts of superoxide. Hydroperoxide formation destroys the aromatic character of the Tyr residue by forming a bicyclic structure via conjugate addition of the terminal amine to the phenol ring. As the N-terminal Tyr and its amino group are essential for their opiate activity, we hypothesize that oxidative modification of this residue should affect the analgesic activity of enkephalins.

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