721-66-4

Basic information

• Product Name: GLYCYL-DL-PHENYLALANINE
• Synonyms: H-GLY-DL-PHE-OH;GLY-DL-PHE;GLYCYL-DL-PHENYLALANINE;N-glycyl-3-phenyl-DL-alanine;N-Glycyl-DL-B-phenylalanine;Gly-D-Phe-OH/Gly-L-Phe-OH,(1:1);rac-(R*)-N-(Glycyl)-2-benzylglycine;rac-(R*)-N-Glycyl-2-benzylglycine
• CAS NO: 721-66-4
• Molecular Formula: C₁₁H₁₄N₂O₃
• Molecular Weight: 222.24
• EINECS: 211-958-6
• Product Categories: Biochemistry;Oligopeptides;Peptide Synthesis;Dipeptides;Dipeptides and Tripeptides;Peptides
• Mol File: 721-66-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 273-275℃ (Decomposition)
• Boiling Point: 492.2 °C at 760 mmHg
• Flash Point: 251.5 °C
• Appearance: /
• Density: 1.259 g/cm³
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly, Heated), Water (Slightly, Sonicated)
• PKA: 3.28±0.10(Predicted)
• CAS DataBase Reference: GLYCYL-DL-PHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: GLYCYL-DL-PHENYLALANINE(721-66-4)
• EPA Substance Registry System: GLYCYL-DL-PHENYLALANINE(721-66-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 721-66-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H14N2O3/c12-7-10(14)13-9(11(15)16)6-8-4-2-1-3-5-8/h1-5,9H,6-7,12H2,(H,13,14)(H,15,16)

Upstream product

• 4530-20-5 BOC-glycine 
• 4530-18-1 2-(tert-butoxycarbonylamino)-3-phenylpropionic acid 
• 60676-54-2 N-phthaloyl-glycyl-β-phenylalanine 
• 150-30-1 Phenylalanine 
• 4703-39-3 N-hippuroyl-3-phenyl-alanine 
• 5540-03-4 Z-Gly-DL-Phe 
• 52555-30-3 N-glycyl-phenylalanine ethyl ester 
• 7765-11-9 N-chloroacetyl-DL-phenylalanine 
• 6913-23-1 2-thioxo-thiazolidin-5-one 

Downstream Products

• 23512-67-6 (+/-)-N-acetylglycylphenylalanine methyl ester 
• 4703-39-3 N-hippuroyl-3-phenyl-alanine 
• 64325-14-0 N-(N-methacryloyl-glycyl)-phenylalanine 
• 1195961-04-6 2-(4-((5-(4-trifluoromethoxyphenyl)furan-2-yl)methylene)-5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid 
• 1195961-01-3 (E)-2-(4-((5-(4-bromo-3-chlorophenyl)furan-2-yl)methylene)-5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid 
• 1195961-03-5 (E)-2-(4-((5-(4-bromo-3-chlorophenyl)thiophen-2-yl)methylene)-5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid 
• 1195961-08-0 (E)-2-(4-((5-(3,4-dichlorophenyl)furan-2-yl)methylene)-5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid 
• 1195961-02-4 (E)-2-(4-((5-(4-bromophenyl)furan-2-yl)methylene)-5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid 
• 34258-14-5 glycyl-D-phenylalanine 
• 1195960-97-4 2-(4-((5-(3,4-dichlorophenyl)furan-2-yl)methylene)-5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid 

Relevant articles and documents

Kinetics of degradation and oil solubility of ester prodrugs of a model dipeptide (Gly-Phe)

Oil-based depot formulations may constitute a future delivery method for small peptides. Thus, a requirement is attainment of sufficient oil solubility for such active compounds. A model dipeptide (Gly-Phe) has been converted into lipophilic prodrugs by esterification at the C-terminal carboxylic acid group. The decomposition kinetics of octyl ester of Gly-Phe (IV) has been investigated at pH 7.4 (37°C) and IV was shown to degrade by first-order kinetics via two parallel pathways (1) intramolecular aminolysis resulting in formation of a 2,5-diketopiperazine and (2) hydrolysis of the ester bond producing the dipeptide. The cyclisation reaction was dominating in the decomposition of methyl (II) butyl (III) octyl (IV) decyl (V) and dodecyl (VI) esters of Gly-Phe at pH 7.4. However, this degradation pathway was almost negligible for pH below 6. During degradation of the dipeptide esters in 80% human plasma pH 7.4 (37°C) a minimal amount of cyclo(-Gly-Phe) was formed. A faster degradation of the esters in 80% human plasma pH 7.4 compared to those in aqueous solution pH 7.4 was suggested to be due to fast cleavage of the peptide bond. Low oil solubilities for Gly-Phe and the hydrochlorides of the dipeptide esters III and VI were observed. Although the solubility of Gly-Phe in oil solutions was enhanced by hydrophobic ion pairing with sodium decyl sulfonate the oil solubility was still less than 1 mg Gly-Phe/ml. By addition of a solubiliser, 10% N,N-dimethylacetamide (DMA), to Viscoleo the solubility of the HIP complexes increased significantly. The present study indicates that sufficient oil solubility might only be obtained for relatively small peptides by using the prodrug approach in combination with solubility enhancing organic solvents like DMA.

The hydroxylamino lysis of N-substituted phthalimide, a method for the prepartion of peptides and N-hydroxypeptides

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