Product Name

  • Name

    H-TYR-GLY-GLY-PHE-MET-OH

  • EINECS 261-335-8
  • CAS No. 58569-55-4
  • Article Data27
  • CAS DataBase
  • Density 1.324 g/cm3
  • Solubility Soluble in water
  • Melting Point 174-177 °C
  • Formula C27H35 N5 O7 S
  • Boiling Point 1052.9 °C at 760 mmHg
  • Molecular Weight 573.67
  • Flash Point 590.6 °C
  • Transport Information
  • Appearance White lyophilised solid
  • Safety 22-24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 58569-55-4 (H-TYR-GLY-GLY-PHE-MET-OH)
  • Hazard Symbols
  • Synonyms Adrenorphin(human), 6-de-L-arginine-7-de-L-arginine-8-de-L-valinamide-; 105: PN:US20030119021 SEQID: 92 unclaimed sequence; 106: PN: US20090048431 SEQID: 105claimed sequence; 10: PN: WO2008008805 SEQID: 10 unclaimed protein; 12: PN:US6258556 SEQID: 12 unclaimed sequence; 132: PN: WO2008125902 SEQID: 122unclaimed sequence; 153: PN: US20030176421 PAGE: 54-55 claimed protein; 16: PN:EP1498113 PAGE: 14 claimed protein; 16: PN: WO2009012472 SEQID: 16 unclaimedsequence; 18: PN: US6284459 SEQID: 33 unclaimed sequence; 18: PN: WO2006068768SEQID: 16 claimed sequence; 1: PN: US6265563 SEQID: 1 unclaimed sequence; 1:PN: WO03102015 SEQID: 1 claimed sequence; 1: PN: WO2004075843 PAGE: 5 unclaimedsequence; 1: PN: WO2005097158 SEQID: 1 unclaimed sequence; 210: PN: WO0069900SEQID: 882 unclaimed sequence; 211: PN: WO0069900 SEQID: 883 unclaimedsequence; 215: PN: WO0069900 SEQID: 887 unclaimed sequence; 25: PN:WO2005095443 SEQID: 25 claimed protein; 2: PN: US20040186059 PAGE: 2 unclaimedsequence; 2: PN: US20080045610 SEQID: 2 unclaimed sequence; 2: PN: WO2004073646TABLE: 3 unclaimed sequence; 2: PN: WO2008011381 SEQID: 58 unclaimed sequence;328: PN: WO2007106799 SEQID: 105 unclaimed sequence; 34: PN: US6319668 SEQID:33 unclaimed sequence; 3: PN: WO2008052043 SEQID: 2 claimed protein; 46: PN:US6017496 PAGE: 120 claimed protein; 4: PN: US20040209344 SEQID: 9 unclaimedsequence; 4: PN: US6395513 SEQID: 7 unclaimed sequence;5-L-Methionine-enkephalin; 5-Methionine enkephalin; 53: PN: US20090104234SEQID: 53 unclaimed protein; 5: PN: US20080039404 SEQID: 5 unclaimed sequence;6: PN: WO0130371 TABLE: 1 unclaimed sequence; 707: PN: US20090175821 SEQID: 882claimed protein; 7: PN: WO0130371 TABLE: 1 unclaimed sequence; 7: PN:WO2008106043 TABLE: 6 claimed protein; 9: PN: WO03061683 FIGURE: 1 unclaimedsequence; 9: PN: WO2004041151 SEQID: 9 unclaimed sequence; Enkephalin,methionine; Human b-endorphin(1-5); L-Methionine-enkephalin; Lupex; Met-enkephalin;Met5-enkephalin; Metenkefalin; Methionine enkephalin;
  • PSA 225.25000
  • LogP 1.80830

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

(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

met-enkephalin

Conditions
ConditionsYield
With p-cresol; dimethylsulfide; hydrogen fluoride at 0℃; for 1h;92%
boc-Tyr-Gly-Gly-Phe-Met-OH
59481-77-5

boc-Tyr-Gly-Gly-Phe-Met-OH

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

Boc-Tyr-Gly-Gly-Phe-Met-OBut

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
With methyl-phenyl-thioether; trifluoroacetic acid for 1h; Ambient temperature;74%
C17H13NO10S2(2-)*2Na(1+)

C17H13NO10S2(2-)*2Na(1+)

C20H19NO10S3(2-)*2Na(1+)

C20H19NO10S3(2-)*2Na(1+)

C24H19NO10S2(2-)*2Na(1+)

C24H19NO10S2(2-)*2Na(1+)

C24H19NO11S2(2-)*2Na(1+)

C24H19NO11S2(2-)*2Na(1+)

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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%
...Expand
Boc-Tyr(Mtb)-Gly-Gly-Phe-Met-OMtb
129398-74-9

Boc-Tyr(Mtb)-Gly-Gly-Phe-Met-OMtb

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

Boc-Tyr(Cl2Bzl)-Gly-Gly-Phe-Met-OBzl

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

N-(diphenylphosphinoyl)tyrosylglycylglycylphenylalanylmethionine

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 6h;40%
Boc-Tyr(tert.-Bu)-Gly-Gly-Phe-Met
62530-43-2

Boc-Tyr(tert.-Bu)-Gly-Gly-Phe-Met

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

Z-Tyr(Bzl)-Gly-Gly-Phe-Met

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

methyl ester of N,O-di-t-butyloxycarbonyl-L-tyrosylglycylglycyl-L-phenylalanyl-L-methionine

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

Z-Tyr-Gly-Gly-Phe-Hcy(Bzl)-OBzl

methyl iodide
74-88-4

methyl iodide

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

methionine-enkephalin sulfoxide

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
With ammonium iodide; dimethylsulfide In trifluoroacetic acid at 0℃;
BocMet-R, Boc-amino acids

BocMet-R, Boc-amino acids

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
Yield given; Multistep reaction;
phospho-Tyr-Gly-Gly-Phe-Met-OH

phospho-Tyr-Gly-Gly-Phe-Met-OH

A

met-enkephalin
58569-55-4

met-enkephalin

B

O-phosphono-L-tyrosine
21820-51-9

O-phosphono-L-tyrosine

C

L-tyrosine
60-18-4

L-tyrosine

D

[des-tyr1]-methionine enkephalin
61370-88-5

[des-tyr1]-methionine enkephalin

Conditions
ConditionsYield
With aminopeptidase M (EC3.4.11.2); 2-amino-2-hydroxymethyl-1,3-propanediol at 37℃; for 1h; pH=7.02; Kinetics; Hydrolysis;
...Expand
-enkephalyl-arg6-phe7

-enkephalyl-arg6-phe7

A

L-arginyl-L-phenylalanine
2047-13-4

L-arginyl-L-phenylalanine

B

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
With angiotensin I converting enzyme In various solvent(s) at 37℃; pH=7.75; Kinetics;
-enkephalyl-arg6-phe7

-enkephalyl-arg6-phe7

A

YG
673-08-5

YG

B

met-enkephalin
58569-55-4

met-enkephalin

C

tyrosylglycylglycine
21778-69-8

tyrosylglycylglycine

D

L-tyrosine
60-18-4

L-tyrosine

Conditions
ConditionsYield
With membrane fraction In various solvents at 37℃; for 1h; pH=7.4; Product distribution; Further Variations:; Reagents;
...Expand
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

Boc-Pro, Boc-Cys(Bzl), Boc-Asn NPE, Boc-Val

Boc-Pro, Boc-Cys(Bzl), Boc-Asn NPE, Boc-Val

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

Methyl ester of N-t-butyloxycarbonyl-L-phenylalanyl-L-methionine

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

methyl N-tert-butoxycarbonyl-L-tyrosyldiglycyl-L-phenylalanyl-L-methioninate

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

N-tert-Butyloxycarbonyl-glycyl-glycyl-L-phenylalanyl-L-methionin-methylester

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

Boc-Phe-O-COO-isoBu

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

hydrochloride of methyl ester of glycylglycyl-L-phenylalanyl-L-methionine

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

L-phenylalaninyl-L-methionine methyl ether p-toluenesulfonate

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

N-tert-butoxycarbonyl-L-phenylalanine

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

hydrochloride of methyl ester of L-phenylalanyl-L-methionine

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

O-(t-butyloxycarbonyl-L-phenylalanyl)-2-pyridylmethylketoxime

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

N-benzyloxycarbonyl-O-benzyl-L-tyrosine

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
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

N-(O-benzyl-N-benzyloxycarbonyl-L-tyrosyl)-glycine ethyl ester

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
3: thioanisole / trifluoroacetic acid / 4 h / 25 °C
View Scheme
Z-Tyr(Bzl)-Gly-N2H3
74916-75-9

Z-Tyr(Bzl)-Gly-N2H3

met-enkephalin
58569-55-4

met-enkephalin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: thioanisole / trifluoroacetic acid / 4 h / 25 °C
View Scheme
fluorescein isothiocyanate
3326-32-7, 27072-45-3

fluorescein isothiocyanate

met-enkephalin
58569-55-4

met-enkephalin

C48H46N6O12S2

C48H46N6O12S2

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

Tyrosylglycyl-glycyl-phenylalanyl-methionine Chemical Properties

Molecular Structure of Tyrosylglycyl-glycyl-phenylalanyl-methionine (CAS No.58569-55-4):
 
Molecular Formula: C27H35N5O7S
Molecular Weight: 573.6611
CAS No: 58569-55-4
H bond acceptors: 12
H bond donors: 8
Freely Rotating Bonds: 18
Polar Surface Area: 145.31 Å2
Index of Refraction: 1.608
Molar Refractivity: 149.86 cm3
Molar Volume: 433.1 cm3
Surface Tension: 61.7 dyne/cm
Density: 1.324 g/cm3
Flash Point: 590.6 °C
Enthalpy of Vaporization: 161.46 kJ/mol
Boiling Point: 1052.9 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
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
InChIKey: YFGBQHOOROIVKG-FKBYEOEOBZ
Std. InChI: InChI=1S/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
Std. InChIKey: YFGBQHOOROIVKG-FKBYEOEOSA-N
IUPAC Name: 2-[[2-[[2-[[2-[[2-Amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid 
Product Categories: Peptide;Opioid receptor and opioid-like receptor
Classification Code: Neurotransmitter Agents

Tyrosylglycyl-glycyl-phenylalanyl-methionine Safety Profile

Safety Statements: 22-24/25
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
F: 3-10-21

Tyrosylglycyl-glycyl-phenylalanyl-methionine Specification

   Tyrosylglycyl-glycyl-phenylalanyl-methionine (CAS No.58569-55-4), its synonyms are [Met5]Enkephalin ; Met-Enkephaline ; N-[N-[N-(N-L-tyrosylglycyl)glycyl]-L-phenylalanyl]-L-methionine  .

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