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

Description

H-GLA-OH, also known as L-gamma-glutamyl-gamma-aminopropionic acid, is a non-proteinogenic L-alpha-amino acid derived from L-glutamic acid with a carboxy group substitution at one of the gamma-hydrogens. It appears as a white powder and has potential applications in various industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
H-GLA-OH is used as a therapeutic agent for its potential benefits in treating various medical conditions. Its unique structure allows it to interact with specific biological targets, making it a promising candidate for drug development.
Used in Cosmetic Industry:
H-GLA-OH is used as an active ingredient in cosmetic products for its potential skin-protecting and rejuvenating properties. Its ability to form complexes with biopolymers and macromolecules can contribute to improved skin health and appearance.
Used in Food Industry:
H-GLA-OH is used as an additive in the food industry for its potential to enhance flavor, texture, and shelf-life of certain products. Its unique chemical properties may also contribute to the development of novel food products with improved nutritional profiles.
Used in Research and Development:
H-GLA-OH is used as a key compound in research and development for its potential applications in various scientific fields. Its unique structure and properties make it an interesting subject for further study and potential development of new technologies and products.

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

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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