Tyr-gly-gly

Base Information

• Chemical Name: Tyr-gly-gly
• CAS No.: 21778-69-8
• Molecular Formula: C13H17N3O5
• Molecular Weight: 295.295
• Hs Code.: 2924299090
• UNII: DS6B3J0V03
• Nikkaji Number: J346.189K
• Wikidata: Q27145057
• NCI Thesaurus Code: C1132
• Metabolomics Workbench ID: 86403
• ChEMBL ID: CHEMBL191422
• Mol file: 21778-69-8.mol

Synonyms:Imreg tripeptide;TGG tripeptide;Tyr-Gly-Gly;tyrosyl-glycyl-glycine;tyrosylglycylglycine;YGG tripeptide

Chemical Property of Tyr-gly-gly

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 4.18E-23mmHg at 25°C
• Melting Point: 193-195℃
• Refractive Index: 1.6
• Boiling Point: 741.8 °C at 760 mmHg
• Flash Point: 402.4 °C
• PSA: 141.75000
• Density: 1.381 g/cm³
• LogP: 0.06110
• Storage Temp.: −20°C
• XLogP3: -3.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 295.11682065
• Heavy Atom Count: 21
• Complexity: 380

Purity/Quality:

98%min ^*data from raw suppliers

(S)-2-(2-(2-Amino-3-(4-hydroxyphenyl)propanamido)acetamido)aceticacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C(=O)NCC(=O)NCC(=O)O)N)O
• Isomeric SMILES: C1=CC(=CC=C1C[C@@H](C(=O)NCC(=O)NCC(=O)O)N)O
• Uses: Tripeptide released from enkephalins by the enzyme enkephalinase.

Technology Process of Tyr-gly-gly

There total 13 articles about Tyr-gly-gly which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 51.0%

methyl (S) [N-(tert-butoxycarbonyl)-O-tert-butyldimethylsilyl]tyrosylglycylglycinate (1332726-69-8) → TBDMS-O-Boc-N-Tyr-Gly-Gly-OH (1332726-72-3) + tyrosylglycylglycine (21778-69-8) + tert-butoxycarbonyl-L-tyrosyl-glycyl-glycine (59481-76-4)

Guidance literature:

With water; lithium hydroxide; In methanol; at 20 ℃; for 17h; Inert atmosphere;

DOI:10.1080/10426507.2010.535398

Reference yield: 34.0%

tetrabutylphosphonium glycinate + L-tyrosine methyl ester HCl (3417-91-2) → tyrosylglycylglycine (21778-69-8)

Guidance literature:

tetrabutylphosphonium glycinate; for 3h; Inert atmosphere;

L-tyrosine methyl ester HCl; In chloroform; at 60 ℃; for 48h;

With acetic acid; In chloroform; at 20 ℃; for 3h;

DOI:10.1002/chem.201501783

Reference yield:

leucine enkephalin acetate (81678-16-2) → L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + YG (673-08-5) + L-Phe-Leu (3303-55-7) + tyrosylglycylglycine (21778-69-8) + L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) + [des-tyr1]-leucine enkephalin (60254-83-3)

Guidance literature:

In water; at 37 ℃; for 6h; Product distribution; Rate constant; enzymes: leucine aminopeptidase , carboxypeptidase B; degradation in extracts of various mucosae (nasal, rectal, vaginal); female White Albino rabbits; different inhibitors (amastatin, thimerosal, thiorphan); pH=5-8;

DOI:10.1002/jps.2600821124

upstream raw materials:

glycylglycine ethyl ester

L-Tyr(OAc) NCA

N-[N-(N-benzyloxycarbonyl-L-tyrosyl)-glycyl]-glycine

N-carbobenzyloxy-O-carbobenzyloxy-L-tyrosylglycylglycine

Downstream raw materials:

Nap-Tyr-Gly-Gly

L-tyrosine

N-carbobenzyloxy-O-carbobenzyloxy-L-tyrosylglycylglycine

diethyl (S,S)-N-[(tert-butoxycarbonyl)tyrosylglycylglycylphenylalanyl]-4-amino-tetrahydro-2H-thiopyran-4-yl-phosphonate