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Tyrosylglycyl-glycyl-phenylalanyl-methionine
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Name

Tyrosylglycyl-glycyl-phenylalanyl-methionine

 EINECS 261-335-8
CAS No. 58569-55-4 Density 1.324 g/cm3
PSA 225.25000 LogP 1.80830
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 N/A Appearance White lyophilised solid
Safety 22-24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 58569-55-4 (H-TYR-GLY-GLY-PHE-MET-OH) Hazard Symbols N/A
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;

Article Data 27

Tyrosylglycyl-glycyl-phenylalanyl-methionine 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

58569-55-4

met-enkephalin

Conditions
ConditionsYield
With p-cresol; dimethylsulfide; hydrogen fluoride at 0℃; for 1h;92%
59481-77-5

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

58569-55-4

met-enkephalin

Conditions
ConditionsYield
With hydrogenchloride; acetic acid for 1h;90%
With hydrogenchloride In acetic acid for 0.5h;85%
82362-16-1

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

58569-55-4

met-enkephalin

Conditions
ConditionsYield
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+)

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%
129398-74-9

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

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%
129398-68-1

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

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%
148715-90-6

N-(diphenylphosphinoyl)tyrosylglycylglycylphenylalanylmethionine

58569-55-4

met-enkephalin

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 6h;40%
62530-43-2

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

58569-55-4

met-enkephalin

Conditions
ConditionsYield
With hydrogenchloride; ethane-1,2-dithiol; methoxybenzene In 1,4-dioxane for 1h; Ambient temperature; Yield given;
74937-32-9

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

58569-55-4

met-enkephalin

Conditions
ConditionsYield
With methyl-phenyl-thioether In trifluoroacetic acid at 25℃; for 4h; Yield given;
81649-52-7

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

58569-55-4

met-enkephalin

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

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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