59765-55-8

Basic information

• Product Name: allyl glycinate
• Synonyms: allyl glycinate;Glycine 2-propenyl ester;Glycine allyl ester;Einecs 261-917-1
• CAS NO: 59765-55-8
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.13046
• EINECS: 261-917-1
• Mol File: 59765-55-8.mol

Chemical Properties

• Boiling Point: 147.3°C at 760 mmHg
• Flash Point: 22.2°C
• Appearance: /
• Density: 1.015g/cm³
• Vapor Pressure: 4.45mmHg at 25°C
• Refractive Index: 1.446
• CAS DataBase Reference: allyl glycinate(CAS DataBase Reference)
• NIST Chemistry Reference: allyl glycinate(59765-55-8)
• EPA Substance Registry System: allyl glycinate(59765-55-8)

Safety Data

• Hazardous Substances Data: 59765-55-8(Hazardous Substances Data)

Usage

Chemical compound

Allyl glycinate

Allyl ester of glycine

An amino acid that is a building block for proteins
Commonly used as a flavoring agent in the food industry
Adds a sweet, nutty, and caramel-like aroma to various products
Used in the production of perfumes and cosmetics for its pleasant scent
Investigated for potential pharmaceutical applications
Potential anti-inflammatory and anti-cancer agent
Further research needed to understand medicinal properties and potential uses

InChI:InChI=1/C5H9NO2/c1-2-3-8-5(7)4-6/h2H,1,3-4,6H2

Upstream product

• 124373-83-7 allyl 2-(tert-butoxycarbonylamino)acetate 
• 107-18-6 allyl alcohol 
• 56-40-6 glycine 
• 75-09-2 dichloromethane 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 120902-57-0 {[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-acetic acid allyl ester 
• 868837-28-9 allyl 2-(2-nitrophenylsulfonamido)acetate 
• 96921-56-1 Allyl N-(benzyloxycarbonyl)glycinate 
• 1393358-73-0 C₂₂H₃₁N₃O₇ 
• 1316832-58-2 allyl 2-(2-hydroxy-2-(4-hydroxyphenyl)acetamido)acetate 
• 1316832-26-4 allyl 2-(2-acetoxy-2-(4-nitrophenyl)acetamido)acetate 
• 1316832-71-9 (E)-allyl 9-(4-(bis(2-nitrobenzyloxy)phosphoryloxy)phenyl)-1-(4-((4-(dimethylamino)phenyl)diazenyl)phenyl)-1,7,10-trioxo-8-oxa-2,6,11-triazatridecan-13-oate 
• 1316832-66-2 C₃₄H₂₉N₄O₁₆P 
• 1316832-63-9 allyl 2-(2-(4-(bis(2-nitrobenzyloxy)phosphoryloxy)phenyl)-2-hydroxyacetamido)acetate 
• 1316833-14-3 tert-butyl (4S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((4-(1-(4-((E)-(4-(dimethylamino)phenyl)diazenyl)phenyl)-1,7,10,13-tetraoxo-8,14-dioxa-2,6,11-triazaheptadec-16-en-9-yl)phenyl)amino)-5-oxopentanoate 
• 1316832-39-9 (E)-allyl 9-(4-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-tert-butoxy-4-oxobutanamido)phenyl)-1-(4-((4-(dimethylamino)phenyl)diazenyl)phenyl)-1,7,10-trioxo-8-oxa-2,6,11-triazatridecan-13-oate 
• 1316833-11-0 tert-butyl (4S)-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-(((4-nitrophenoxy)carbonyl)oxy)-2-oxoethyl)phenyl)amino)-5-oxopentanoate 
• 1316832-35-5 tert-butyl 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(4-(2-(2-(allyloxy)-2-oxoethylamino)-1-((4-nitrophenoxy)carbonyloxy)-2-oxoethyl)phenylamino)-4-oxobutanoate 
• 1316833-02-9 tert-butyl (4S)-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-hydroxy-2-oxoethyl)phenyl)amino)-5-oxopentanoate 

Relevant articles and documents

Large cyclic peptides as cores of multivalent ligands: Application to inhibitors of receptor binding by cholera toxin

Large cyclic decapeptides (up to 50-atom ring) were synthesized efficiently on the solid phase with allylester protection of the carboxyl terminus during elongation. Pentavalent ligands, in a "core-linker-finger" modular setup, were assembled by using these cyclic peptide cores to demonstrate large affinity gains for inhibition of surface receptor binding by the cholera toxin B pentamer. The results suggest that the peptide cores retain expanded conformation in solution so that shorter flexible linkers are needed for larger peptide cores to achieve the best inhibitory results.

Solid-phase synthesis of peptide selenoesters: Via a side-chain anchoring strategy

Peptide selenoesters have recently emerged as key building blocks for the ligation-based assembly of large polypeptides and proteins. Herein, we report an efficient solid-phase method for the high yielding and epimerisation-free synthesis of peptide selenoesters using a side-chain immobilisation strategy.

Multicolor, one- and two-photon imaging of enzymatic activities in live cells with fluorescently quenched activity-based probes (qABPs)

Fluorescence imaging provides an indispensable way to locate and monitor biological targets within complex and dynamic intracellular environments. Of the various imaging agents currently available, small molecule-based probes provide a powerful tool for live cell imaging, primarily due to their desirable properties, including cell permeability (as a result of their smaller sizes), chemical tractability (e.g., different molecular structures/designs can be installed), and amenability to imaging a wide variety of biological events. With a few exceptions, most existing small molecule probes are however not suitable for in vivo bioimaging experiments in which high-resolution studies of enzyme activity and localization are necessary. In this article, we reported a new class of fluorescently Quenched Activity-Based Probes (qABPs) which are highly modular, and can sensitively image (through multiple enzyme turnovers leading to fluorescence signal amplification) different types of enzyme activities in live mammalian cells with good spatial and temporal resolution. We have also incorporated two-photon dyes into our modular probe design, enabling for the first time activity-based, fluorogenic two-photon imaging of enzyme activities. This, hence, expands the repertoire of smart, responsive probes currently available for live cell bioimaging experiments.

Diversity-oriented synthesis of a cytisine-inspired pyridone library leading to the discovery of novel inhibitors of Bcl-2

Four enantiopure cytisine-inspired scaffolds can be accessed via a versatile pyrrolidine template derived from a stereocontrolled [3+2] azomethine ylide-alkene cycloaddition. Differential ester protection allows for the selective formation of either a bridged bicyclic or tricyclic scaffold via pyridone cyclization. Solid-phase diversification of the pyridone scaffolds yielded a diverse library of 15,000 compounds enabling the discovery of a novel class of Bcl-2 inhibitors.

Total synthesis of lysobactin

Antibiotic resistance has become a significant public health concern. Antibiotics that belong to new structural classes and manifest their biological activity via novel mechanisms are urgently needed. Lysobactin, a depsipeptide antibiotic has displayed very strong antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) as well as vancomycin-resistant enterococci (VRE) with minimum inhibitory concentrations (MICs) ranging from 0.39 to 0.78 μg/mL. The MIC values against VRE were more than 50-fold lower than those reported for vancomycin itself. Lysobactin was found to inhibit nascent peptidoglycan formation; however, this activity was not antagonized in the presence of N-acyl-L-Lys-D-Ala-D-Ala, the binding domain on the cell wall precursors that is utilized by vancomycin. Thus, lysobactin represents a promising agent for the treatment bacterial infections due to resistant pathogens. We describe a convergent synthesis of lysobactin that relies upon a highly efficient macrocyclization reaction to assemble the 28-membered cyclic depsipeptide. This synthesis provides the foundation for further study of the mode of action utilized by lysobactin and its analogues.

Convenient synthesis of photoaffinity probes and evaluation of their labeling abilities

Convenient synthesis of a variety of photoaffinity probes was accomplished by utilizing our Ns strategy and novel resin. The synthetic probes were evaluated via the labeling ability with the preseniline 1 C-terminal fragments, which was identified as a therapeutic target for Alzheimer's disease.

Transglutaminase inhibitors

This invention is directed to compounds of the formula: STR1 or an optical isomer thereof, or a pharmaceutically acceptable salt thereof, wherein: n is 0, 1 or 2; p and q are independently 0, 1 or 2 and the sum of (p+q) is less than or equal to 3; X is selected from the group consisting of: halo; --OR2, --SR2, --S(O)R2, --S(O)2 R2, and --S(O)2 NHR2, wherein R2 is lower alkyl, mono-, di- or tri-fluoro alkyl of 2 or 3 carbon atoms, optionally substituted aryl; R is H or an N-protecting group; R1 is alkylthio, arylthio, amino, alkylamino, optionally substituted arylamino, or optionally substituted aralkylamino; and when the sum of n+p+q is greater than or equal to one, R1 is also hydroxy, alkoxy, or aralkoxy; and each (aa) is independently an α-amino acid residue with an optionally protected amino acid side chain.

SYNTHESIS OF α-ALLYL-α-AMINO ACIDS BY MEANS OF A PALLADIUM CATALYIZED INTRAMOLECULAR REARRANGEMENT

Allylic esters of imines of amino acids provide α-alkylated-α-amino acids in good yields, on rearrangement by catalytic quantities of Pd(0) complexes.