23576-42-3

Basic information

• Product Name: PHE-GLY-GLY
• Synonyms: PHE-GLY-GLY;H-PHE-GLY-GLY-OH;L-PHENYLALANYLGLYCYLGLYCINE;phenylalanyl-glycyl-glycine;L-Phe-Gly-Gly-OH;Phe-Gly-Gly-OH
• CAS NO: 23576-42-3
• Molecular Formula: C₁₃H₁₇N₃O₄
• Molecular Weight: 279.29
• Product Categories: Dipeptides and Tripeptides;Peptides;Tripeptides
• Mol File: 23576-42-3.mol

Chemical Properties

• Melting Point: 235-236 °C (decomp)
• Boiling Point: 667.3 °C at 760 mmHg
• Flash Point: 357.4 °C
• Appearance: White powder
• Density: 1.296 g/cm³
• Vapor Pressure: 1.02E-18mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: −20°C
• PKA: 3.30±0.10(Predicted)
• CAS DataBase Reference: PHE-GLY-GLY(CAS DataBase Reference)
• NIST Chemistry Reference: PHE-GLY-GLY(23576-42-3)
• EPA Substance Registry System: PHE-GLY-GLY(23576-42-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 23576-42-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
PHE-GLY-GLY is used as a building block for the development of new pharmaceutical compounds due to its unique structure and the ability to interact with other molecules. Its potential applications in drug design and development can be attributed to the specific arrangement of amino acids, which may allow for targeted interactions with biological targets.
Used in Cosmetic Industry:
PHE-GLY-GLY is used as an ingredient in cosmetic products for its potential moisturizing and skin-conditioning properties. The presence of glycine, a natural component of collagen, may contribute to the overall skin health and hydration when used in cosmetic formulations.
Used in Food Industry:
PHE-GLY-GLY can be used as a flavor enhancer or additive in the food industry. The presence of L-phenylalanine, an essential amino acid, may contribute to the overall taste and aroma of certain food products, making it a valuable component in the development of new flavors and taste profiles.
Used in Research and Development:
PHE-GLY-GLY serves as a valuable research tool for studying the properties and interactions of amino acids in various biological systems. Its unique structure allows scientists to investigate the role of specific amino acid sequences in protein folding, stability, and function, furthering our understanding of biological processes and potential therapeutic applications.

InChI:InChI=1/C13H17N3O4/c14-10(6-9-4-2-1-3-5-9)13(20)16-7-11(17)15-8-12(18)19/h1-5,10H,6-8,14H2,(H,15,17)(H,16,20)(H,18,19)

Upstream product

• 37700-64-4 (5S)-5-benzyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oic acid 
• 75720-06-8 1-O-(L-phenylalanylglycylglycyl)-β-D-glucopyranose mono-oxalate 
• 29022-11-5 N-(fluoren-9-ylmethoxycarbonyl)glycine 
• 35661-40-6 N-Fmoc L-Phe 

Downstream Products

• 119460-19-4 (2-{(S)-2-[(S)-3-(Acetylamino-methylsulfanyl)-2-tert-butoxycarbonylamino-propionylamino]-3-phenyl-propionylamino}-acetylamino)-acetic acid 
• 63-91-2 L-phenylalanine 
• 56-40-6 glycine 
• 143718-32-5 Phe-Gly-Gly-OMe 
• 952312-66-2 C₁₇H₂₁N₃O₅ 
• 119439-58-6 C₅₈H₉₇N₁₇O₁₆S 
• 117951-71-0 C₆₃H₁₀₉N₁₇O₁₇S 
• 119439-67-7 (2-{(S)-2-[(S)-3-(Acetylamino-methylsulfanyl)-2-tert-butoxycarbonylamino-propionylamino]-3-phenyl-propionylamino}-acetylamino)-acetic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester 
• 119082-79-0 [2-((S)-2-{(S)-3-(Acetylamino-methylsulfanyl)-2-[(S)-3-tert-butoxy-2-((S)-3-tert-butoxy-2-tert-butoxycarbonylamino-propionylamino)-propionylamino]-propionylamino}-3-phenyl-propionylamino)-acetylamino]-acetic acid 
• 117951-67-4 (2-{(S)-2-[(S)-3-(Acetylamino-methylsulfanyl)-2-amino-propionylamino]-3-phenyl-propionylamino}-acetylamino)-acetic acid 

Relevant articles and documents

N -boc deprotection and isolation method for water-soluble zwitterionic compounds

A highly efficient TMSI-mediated deprotection and direct isolation method to obtain zwitterionic compounds from the corresponding N-Boc derivatives has been developed. This method has been demonstrated in the final deprotection/isolation of the β-lactamase inhibitor MK-7655 as a part of its manufacturing process. Further application of this process toward other zwitterionic compounds, such as dipeptides and tripeptides, has been successfully developed. Furthermore, a catalytic version of this transformation has been demonstrated in the presence of BSA or BSTFA.

A genetically encodable ligand for transfer hydrogenation

Simple tripeptides are shown here to be versatile ligands for iridium-catalyzed transfer hydrogenations affording large acceleration effects. A water-soluble iridium complex with Gly-Gly-Phe, for example, catalyzes the reduction of diverse ketones, aldehydes, and imines by formate with turnover frequencies rivaling or outperforming those of established ligand systems. Regioselective reduction of coenzyme NAD+ to NADH illustrates the potential utility of this system for biotechnological applications. Because peptides are genetically encodable, they represent an attractive class of foldamer ligands for creating artificial metalloenzymes.

ATRIOPEPTINS. II. SYNTHESIS OF N-TERMINAL FRAGMENTS

Peptides, corresponding to the N-terminal sequence in atriopeptins, were synthesized by classical methods of peptide chemistry in solutions.The obtained peptides were characterized by various physicochemical methods.The scheme and methods of the synthesis are discussed.

SYNTHESIS, PROPERTIES, AND REACTIONS OF α- AND β-D-GLUCOPYRANOSYL ESTERS OF SOME TRIPEPTIDES

The 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonyltripeptidyl)-D-glucopyranoses 1, 8, and 13 were synthesised from 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose and the active esters of the appropriate N-protected tripeptides (Gly-Gly-Gly-, L-Phe-Gly-Gly-, and Gly-Gly-L-Phe-) in the presence of imidazole; the anomeric mixtures were resolved and the α and β anomers characterised.The β anomer of 13, containing the L and D enantiomers (ratio ca. 3:1) of Gly-Gly-Phe- as the aglycon, could be resolved by column chromatography into the pure isomeric forms.Catalytic hydrogenolysis of the β anomers, in the presence and absence of a strong acid, yielded the free 1-esters 2β, 9β, and 14β, which were characterised as the mono-oxalate or trifluoroacetate salts and as free bases.Similarly, the α anomers afforded 2α, 9α, and 14α, whereas omission of the strong acid led to accompanying 1 --> 2 acyl migration, to give the 2-O-acyl derivatives.All of the compounds prepared were converted into the N-acetyl and/or peracetylated derivatives.The 1-esters 2β and 9β, both in the charged and uncharged form, and the trifluoroacetate salt of 14β, are susceptible to cleavage by β-D-glucosidase; the enzyme had no effect on the uncharged form of 14β.This difference between 14β and its salt is discussed in conformational terms.