53445-96-8

Basic information

• Product Name: 1-Carboxyglutamic Acid
• Synonyms: 1-Carboxyglutamic Acid
• CAS NO: 53445-96-8
• Molecular Formula: C6H9 N O6
• Molecular Weight: 0
• Mol File: 53445-96-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 418°Cat760mmHg
• Flash Point: 206.6°C
• Appearance: /
• Density: 1.649g/cm³
• CAS DataBase Reference: 1-Carboxyglutamic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Carboxyglutamic Acid(53445-96-8)
• EPA Substance Registry System: 1-Carboxyglutamic Acid(53445-96-8)

Safety Data

• Hazardous Substances Data: 53445-96-8(Hazardous Substances Data)

Usage

Classification

Non-proteinogenic amino acid

Occurrence

Found in many proteins involved in blood clotting and bone metabolism

Synthesis

Synthesized in the liver

Unique feature

Contains a gamma-carboxyglutamate residue

Function in blood coagulation

Essential for the proper functioning of proteins in the blood coagulation cascade

Calcium ion binding

Important for the binding of calcium ions, which are necessary for the activation of proteins in blood clotting

Role in bone metabolism

Presence in bone proteins contributes to the regulation of bone mineralization

Biological significance

Highlights the importance of 1-carboxyglutamic acid in maintaining the proper functioning of blood clotting and bone metabolism processes.

Upstream product

• 56877-44-2 γ,γ'-Di-tert-butyl-DL-γ-carboxyglutamic acid 
• 60686-51-3 γ,γ'-di-tert-butyl-L-γ-carboxyglutamic acid 
• 71424-98-1 (S)-2-Benzyloxycarbonyl-4-benzyloxycarbonylamino-pentanedioic acid dibenzyl ester 
• 95586-48-4 N-tert-butyloxycarbonyl-L-γ-carboxyglutamic acid 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 56877-43-1 N-(benzyloxycarbonyl)-γ,γ-di-tert-butyl-D-γ-carboxyglutamic acid 
• 56877-43-1 Z-DL-Gla(OtBu)2-OH 
• 97458-26-9 N-benzyloxycarbonyl-γ-carboxy-L-glutamic acid 
• 97458-26-9 N-benzyloxycarbonyl-γ-carboxy-DL-glutamic acid 
• 60686-50-2 N-(benzyloxycarbonyl)-γ,γ-di-tert-butyl-L-γ-carboxyglutamic acid 
• 56877-40-8 Z-γ,γ,-di-tert-butyl-D,L-carboxyglutamic acid methyl ester 
• 120824-79-5 N-benzyloxycarbonyl-γ-carboxy-L-glutamic acid α-phenylhydrazide 
• 120824-81-9 diethyl benzyloxycarbonyl-γ-carboxy-DL-pyroglutamate 

Downstream Products

• 87770-02-3 4,4-dicarboxy-5-(p-methoxyphenyl)proline 
• 87770-00-1 4,4-dicarboxy-5-phenylproline 
• 87770-01-2 4,4-dicarboxy-5-(p-nitrophenyl)proline 

Relevant articles and documents

Amino acids and peptides. 44. Synthesis of DL-gamma-carboxyglutamic acid, a new amino acid.

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D(-)- and L(+)-gamma-carboxyglutamic acid (Gla): resolution of synthetic Gla derivatives.

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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.