21778-69-8

Basic information

• Product Name: H-TYR-GLY-GLY-OH
• Synonyms: TYR-GLY-GLY;H-TYR-GLY-GLY-OH;L-TYROSYLGLYCYLGLYCINE;tyrosyl-glycyl-glycine;TYR-GLY-GLY CRYSTALLINE 99%;tyr-gly-glycrystalline;L-Tyr-Gly-Gly-OH;L-TYROSYLGLYCYGLYCINE
• CAS NO: 21778-69-8
• Molecular Formula: C₁₃H₁₇N₃O₅
• Molecular Weight: 295.29
• Product Categories: amino
• Mol File: 21778-69-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 193-195℃
• Boiling Point: 741.8 °C at 760 mmHg
• Flash Point: 402.4 °C
• Appearance: White crystalline powder
• Density: 1.381
• Vapor Pressure: 4.18E-23mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: −20°C
• CAS DataBase Reference: H-TYR-GLY-GLY-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-TYR-GLY-GLY-OH(21778-69-8)
• EPA Substance Registry System: H-TYR-GLY-GLY-OH(21778-69-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 21778-69-8(Hazardous Substances Data)

Usage

Description

H-TYR-GLY-GLY-OH, also known as a tripeptide, is a compound derived from the enzymatic release of enkephalins by the enzyme enkephalinase. It is characterized by its white to off-white powdery appearance and is composed of three amino acid residues, specifically tyrosine, glycine, and another glycine molecule.

Uses

Used in Pharmaceutical Industry:
H-TYR-GLY-GLY-OH is used as an intermediate in the synthesis of various pharmaceutical compounds for its role in the breakdown of enkephalins. Its presence is crucial for the development of drugs targeting the enkephalinase enzyme, which is involved in pain regulation and has potential applications in pain management and treatment of opioid addiction.
Used in Research and Development:
In the field of research and development, H-TYR-GLY-GLY-OH serves as a valuable compound for studying the mechanisms of enkephalinase and its role in pain perception. It can be utilized in the design and testing of novel inhibitors or activators of this enzyme, contributing to the advancement of pain management therapies and a better understanding of the underlying biochemical processes.
Used in Cosmetics Industry:
H-TYR-GLY-GLY-OH may also find applications in the cosmetics industry, where it could be used as an active ingredient in anti-aging or skin care products. Its role in the breakdown of enkephalins might offer potential benefits for skin health and regeneration, although further research would be required to explore these possibilities.
Used in Analytical Chemistry:
As a specific tripeptide, H-TYR-GLY-GLY-OH can be employed in analytical chemistry for the development of assays and tests to detect and quantify enkephalinase activity. This can be particularly useful in research settings and for the development of diagnostic tools related to pain disorders and opioid use.

InChI:InChI=1/C13H17N3O5/c14-10(5-8-1-3-9(17)4-2-8)13(21)16-6-11(18)15-7-12(19)20/h1-4,10,17H,5-7,14H2,(H,15,18)(H,16,21)(H,19,20)

Upstream product

• 67834-81-5 N-carbobenzyloxy-O-carbobenzyloxy-L-tyrosylglycylglycine 
• 3417-91-2 L-tyrosine methyl ester HCl 
• 75790-53-3 Dynorphin 1-8 
• 81678-16-2 leucine enkephalin acetate 
• 1332726-69-8 methyl (S) [N-(tert-butoxycarbonyl)-O-tert-butyldimethylsilyl]tyrosylglycylglycinate 
• 51514-13-7 O-acetyl-N-benzyloxycarbonyl L-tyrosine 
• 51514-08-0 O-acetyl-N-benzyloxycarbonyl-L-tyrosyl chloride 
• 60566-43-0 Tert-butyloxycarbonyltyrosyl-glycyl-glycine Benzyl Ester 
• 82362-17-2 (S)-2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methylsulfanyl-butyric acid; compound with acetic acid 
• 74072-21-2 N-[N-(N-benzyloxycarbonyl-L-tyrosyl)-glycyl]-glycine 
• 627-74-7 glycylglycine ethyl ester 
• 23224-65-9 L-Tyr(OAc) NCA 

Downstream Products

• 1332726-71-2 diethyl (S,S)-N-[(tert-butoxycarbonyl)tyrosylglycylglycylphenylalanyl]-4-amino-tetrahydro-2H-thiopyran-4-yl-phosphonate 
• 126789-60-4 N-carbobenzyloxy-O-carbobenzyloxy-L-tyrosylglycylglycyl-L-phenylalanine 4-(methylsulfonyl)phenyl ester 
• 126789-57-9 N-carbobenzyloxy-O-carbobenzyloxy-L-tyrosylglycylglycyl-L-phenylalanine 4-(methylthio)phenyl ester 
• 191591-09-0 C₄₃H₅₇N₅O₁₃ 
• 191590-74-6 (2-{(S)-3-(4-Hydroxy-phenyl)-2-[(E)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-acryloylamino]-propionylamino}-acetylamino)-acetic acid methyl ester 
• 191591-08-9 (2-{(S)-3-(4-Hydroxy-phenyl)-2-[(E)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-acryloylamino]-propionylamino}-acetylamino)-acetic acid 
• 511546-47-7 C₆₀H₇₉N₉O₂₈ 
• 191591-11-4 L-tyrosylglycylglycine methyl ester 
• 67834-81-5 N-carbobenzyloxy-O-carbobenzyloxy-L-tyrosylglycylglycine 
• 23506-48-1 N-Ac-L-Tyr-Gly-Gly 
• 60-18-4 L-tyrosine 
• 140225-79-2 Nap-Tyr-Gly-Gly 

Relevant articles and documents

Coupling-Reagent-Free Synthesis of Dipeptides and Tripeptides Using Amino Acid Ionic Liquids

A general method for the synthesis of dipeptides has been developed, which does not require any coupling reagents. This method is based on the reaction of readily available HCl salts of amino acid methyl esters with tetrabutylphosphonium amino acid ionic liquids. The isolation procedure of stepwise treatment with AcOH is easy to carry out. The method was extended to the synthesis of tripeptide, tyrosyl-glycyl-glycine, present in IMREG-1, also.

Thioamides: Synthesis, stability, and immunological activities of thioanalogues of imreg. Preparation of new thioacylating agents using fluorobenzimidazolone derivatives

Imreg (Tyr1-Gly2-Gly3) is a well-known immunostimulant. However, it possesses a short half-life. Stabilized analogues of Imreg were prepared by a regioselective insertion in which peptide bonds at position 1,2 or 2,3 were

Transmucosal delivery of methionine enkephalin. I: Solution stability and kinetics of degradation in various rabbit mucosa extracts

To evaluate the feasibility of transmucosal delivery of methionine enkephalin (Tyr-Gly-Gly-Phe-Met; Met-Enk), it is important to first investigate its physicochemical and enzymatic stability. The kinetics of degradation of Met-Enk in aqueous solution was determined at pH 2.01-9.84 and 37-45 °C by high-performance liquid chromatography. The first-order rate constant (k) was calculated, and the log k-pH profile showed that Met-Enk is most stable at pH ~5.0. Various mucosae excised from rabbit were mounted on Valia-Chien permeation cells and exposed to isotonic phosphate buffer at physiologic pHs. Mucosal and serosal extracts were collected from the donor and receptor solutions, respectively. The degradation of Met-Enk in the extracts followed first-order kinetics, but no significant difference in the degradation rates was observed between mucosal and serosal extracts, regardless of the type of mucosa used. Degradation was most rapid in the extracts of rectal mucosa, followed by vaginal and nasal mucosae. The major metabolites were Des-Tyr-Met-Enk and Tyrosine (Tyr), indicating the enzymatic hydrolysis by aminopeptidases. However, the data also suggested that dipeptidyl peptidase and dipeptidyl carboxypeptidase could play some roles in the degradation of Met-Enk. The degradation pathways of Met-Enk were further explored by concomitantly determining the formation of smaller metabolites of primary hydrolytic fragments of Met-Enk in the mucosal extracts.