5349-80-4

Basic information

• Product Name: AMINO ACID HYDROXAMATES GLYCINE HYDROXAMATE
• Synonyms: 2-AMINO-N-HYDROXY-ACETAMIDE;AMINO ACID HYDROXAMATES GLYCINE HYDROXAMATE;GLYCINE HYDROXAMATE;GLYCINE HYDROXAMIC ACID;acetamide, 2-amino-N-hydroxy-;1-Hydroxy-2-aminoethanone oxime;2-Aminoacetohydroximic acid;Aminoacetohydroxamic acid
• CAS NO: 5349-80-4
• Molecular Formula: C₂H₆N₂O₂
• Molecular Weight: 90.08
• Product Categories: A - H;Amino Acids;Modified Amino Acids
• Mol File: 5349-80-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 131°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.311g/cm³
• Vapor Pressure: 5.34E-08mmHg at 25°C
• Refractive Index: 1.582
• Storage Temp.: −20°C
• PKA: pK1:7.1;pK2:9.1 (25°C)
• CAS DataBase Reference: AMINO ACID HYDROXAMATES GLYCINE HYDROXAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: AMINO ACID HYDROXAMATES GLYCINE HYDROXAMATE(5349-80-4)
• EPA Substance Registry System: AMINO ACID HYDROXAMATES GLYCINE HYDROXAMATE(5349-80-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 5349-80-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A hydroxamic acid obtained by formal condensation of the carboxy group of glycine with the amino group of hydroxylamine.

InChI:InChI=1/C14H18N2O/c1-14(2)9-10-6-4-5-7-11(10)12(16-14)8-13(17)15-3/h4-8,16H,9H2,1-3H3,(H,15,17)/b12-8-

Upstream product

• 7803-49-8 hydroxylamine 
• 35985-26-3 glycyl adenylate 
• 556-50-3 glycylglycine 
• 598-41-4 H-Gly-NH₂ 

Downstream Products

• 64163-13-9 1-hydroxy-5-phenyl-2(1H)-pyrazinone 
• 13704-65-9 2-<4-Methyl-benzylidenamino>-essigsaeure-hydroxyamid 
• 13704-64-8 2-<4-Nitro-benzylidenamino>-essigsaeure-hydroxyamid 
• 13704-63-7 2-Benzylidenamino-essigsaeure-hydroxyamid 
• 66313-29-9 1-hydroxy-2(1H)-pyrazinone 
• 78754-80-0 5,6-diphenyl-1-hydroxy-2-oxo-1,2-dihydropyrazine 

Relevant articles and documents

Metal-catalyzed hydroxylaminolysis of unactivated amide and peptide bonds.

Kinetics of the hydroxylaminolysis of acetamide, glycinamide, glycylglycine and triglycine have been studied in the range of temperatures 37-60 degrees C as a function of pH and hydroxylamine concentration. Rate constants for specific acid, general-acid and general-base catalyzed pathways have been determined for all substrates (for glycine derivatives rate constants for different protonation forms were obtained). Testing different metal ions as possible reaction catalysts revealed a significant catalytic effect of Zn(II) on the hydroxylaminolysis of glycine substrates, but not acetamide. On the basis of the kinetic results, a mechanism of Zn(II) catalysis is proposed, which involves the coordination of the metal ion to the alpha-amino group of the substrate and the base-assisted nucleophilic attack of hydroxylamine on the bound substrate. The product analysis by proton NMR shows that the primary reaction product in the catalytic reaction is glycine hydroxamic acid, which undergoes further Zn(II)-catalyzed hydrolysis to glycine. Thus the final result of the Zn(II)-catalyzed treatment of peptides by hydroxylamine is hydrolytic cleavage.