53861-57-7

Basic information

• Product Name: H-GLA-OH
• Synonyms: L-GAMMA-CARBOXYGLUTAMIC ACID;H-G-CARBOXY-L-GLU-OH;H-G-CARBOXY-L-GLUTAMIC ACID;H-GAMMA-CARBOXY-GLU-OH;H-GAMMA-CARBOXY-GLUTAMIC ACID;H-GLA-OH;H-L-GLA-OH;H-L-GLU(GAMMA-COOH)-OH
• CAS NO: 53861-57-7
• Molecular Formula: C₆H₉NO₆
• Molecular Weight: 191.14
• EINECS: 258-825-9
• Product Categories: A - H;Amino Acids;Modified Amino Acids;amino acids
• Mol File: 53861-57-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 167-167.5° (dec)
• Boiling Point: 326.86°C (rough estimate)
• Flash Point: 206.6 °C
• Appearance: /
• Density: 1.5784 (rough estimate)
• Vapor Pressure: 3.71E-08mmHg at 25°C
• Refractive Index: 1.4860 (estimate)
• Storage Temp.: −20°C
• PKA: 1.7(at 25℃)
• Merck: 13,1839
• CAS DataBase Reference: H-GLA-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-GLA-OH(53861-57-7)
• EPA Substance Registry System: H-GLA-OH(53861-57-7)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 53861-57-7(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Definition

ChEBI: A non-proteinogenic L-alpha-amino acid that is L-glutamic acid in which one of the gamma-hydrogens is substituted by a carboxy group.

InChI:InChI=1/C6H9NO6/c7-3(6(12)13)1-2(4(8)9)5(10)11/h2-3H,1,7H2,(H,8,9)(H,10,11)(H,12,13)/t3-/m0/s1

Upstream product

• 97458-26-9 N-benzyloxycarbonyl-γ-carboxy-L-glutamic acid 
• 60686-50-2 N-(benzyloxycarbonyl)-γ,γ-di-tert-butyl-L-γ-carboxyglutamic acid 
• 71389-34-9 (S)-4-[1-Dimethylamino-meth-(E)-ylidene]-5-oxo-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 
• 108732-27-0 N-(tert-butyloxycarbonyl)-γ,γ-dibenzyl-L-γ-carboxyglutamic acid α-tert-butyl ester 
• 97458-26-9 N-benzyloxycarbonyl-γ-carboxy-DL-glutamic acid 
• 120824-79-5 N-benzyloxycarbonyl-γ-carboxy-L-glutamic acid α-phenylhydrazide 
• 120824-81-9 diethyl benzyloxycarbonyl-γ-carboxy-DL-pyroglutamate 
• 108732-22-5 (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-2-hydroxymethyl-5-pyrrolidone 
• 108732-20-3 (2S)-1-(tert-Butoxycarbonyl)-2-<(tert-butyldimethylsilyl)oxymethyl>pyrrolidine 
• 108732-29-2 benzyl 1-(tert-butoxycarbonyl)-4-(benzyloxycarbonyl)-2L,4DL-5-oxoprolinate 
• 81658-26-6 tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 95586-48-4 N-tert-butyloxycarbonyl-L-γ-carboxyglutamic acid 

Relevant articles and documents

USE OF COMPOUNDS IN THE TREATMENT OF ISCHEMIA AND NEURODEGENERATION

TPP II (tripeptidyl peptidase II) inhibitors are useful in the treatment of a neurodegenerative disease, for example Alzheimer's, Parkinson's or Huntingdon's disease or an ischemic condition, for example stroke and cardiac infarction. Suitable compounds comprise tripeptide compounds of general formula RN1RN2N-A1-A2-A3-CO—RC1 wherein RN1, RN2, A1, A2, A3 and RC1 are as defined herein, and which include for example the tripeptide sequences GLA and GPG.

The synthesis and properties of Gla- and Phe-containing analogues of cyclic RGD pentapeptides

Cyclopentapeptides containing the Arg-Gly-Asp motif have been synthesised using solid-phase assembly of side-chain-protected linear precursors, followed by solution-phase cyclisation. The replacement of the Asp residue by γ-carboxyglutamic acid (Gla) is a novel feature which gives rise to an analogue which inhibits cell adhesion, yet its congeners do not show activity in binding assays with recombinant integrin receptors. NMR techniques support a β/γ-turn conformation in most of the analogues. The Royal Society of Chemistry 2000.

A New Approach for the Total Synthesis of L-γ-Carboxyglutamic Acid: Utility of Ruthenium Tetroxide Oxidation

A new and convenient synthesis of optically pure L-γ-carboxyglutamic acid (L-Gla)(1) from L-proline as a chiral source was developed.Protection of N-tert-butyloxycarbonyl(Boc)prolinol (4) with a tert-butyldimethylsilyl group followed by oxidation with ruthenium tetroxide (RuO4) afforded the corresponding lactam compound (6), which was carboxylated with lithium diisopropylamide and benzyloxycarbonylimidazole to afford the 4-benzyloxycarbonyl lactam derivative (7).Selective removal of the silyl group from 7, followed by oxidation of the resulting alcohol (8) with pyridinium dichromate gave the carboxylic acid, which was converted into the ester derivatives (10b-d).Cleavage of the lactam bond of 10b with excess benzyl alcohol in the presence of triethylamine gave γ,γ,α-tribenzyl N-Boc-L-γ-carboxyglutamate (11).Finally, 11 was hydrogenated over Pd on charcoal and deprotected with trifluoroacetic acid to produce L-γ-carboxyglutamic acid (1).Keywords - L-γ-carboxyglutamic acid; ruthenium tetroxide oxidation; carboxylation; L-proline; L-prolinol; 1-benzyloxycarbonylimidazole; 4-benzyloxycarbonyl-1-tert-butyloxycarbonyl-L-pyroglutamic acid ester; catalytic hydrogenation; trifluoroacetic acid deprotection