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Synthesis and Kinetic Characterisation of Water-Soluble Fluorogenic Acyl Donors for Transglutaminase 2
- Source :
- Chembiochem : a European journal of chemical biology. 17(13)
- Publication Year :
- 2016
-
Abstract
- Small glutamate-containing peptides bearing coumarin derivatives as fluorescent leaving groups attached to the γ-carboxylic acid group of the Glu residue were synthesised and investigated with regard to their potential to act as substrates for transglutaminase 2 (TGase 2). Their synthesis was accomplished by an efficient solid-phase approach. The excellent water solubility of the compounds enabled their extensive kinetic characterisation in the context of TGase 2-catalysed hydrolysis and aminolysis. The influence of the coumarin skeleton's substitution pattern on the kinetic properties was studied. Derivatives containing 7-hydroxy-4-methylcoumarin (HMC) revealed properties superior to those of their 7-hydroxycoumarin counterparts; analogous amides are not accepted as substrates. Z-Glu(HMC)-Gly-OH, which exhibited the best substrate properties out of the investigated derivatives, was selected for representative kinetic characterisation of acyl acceptor substrates and irreversible inhibitors.
- Subjects :
- 0301 basic medicine
Tissue transglutaminase
Phosphines
Guinea Pigs
Biotin
Biochemistry
Antioxidants
Piperazines
Iodoacetamide
03 medical and health sciences
Hydrolysis
Residue (chemistry)
chemistry.chemical_compound
Solid-phase synthesis
Aminolysis
Glutamates
Coumarins
GTP-Binding Proteins
Organic chemistry
Aminoacetonitrile
Animals
Humans
Protein Glutamine gamma Glutamyltransferase 2
Amines
Molecular Biology
Enzyme Assays
Fluorescent Dyes
Aqueous solution
Transglutaminases
biology
Lysine
Organic Chemistry
Coumarin
Acceptor
Dithiothreitol
Kinetics
030104 developmental biology
chemistry
biology.protein
Molecular Medicine
Oligopeptides
Subjects
Details
- ISSN :
- 14397633
- Volume :
- 17
- Issue :
- 13
- Database :
- OpenAIRE
- Journal :
- Chembiochem : a European journal of chemical biology
- Accession number :
- edsair.doi.dedup.....1067a3b825f850a20d1c585610b00969