Wodtke, Robert ORCID: 0000-0001-7462-7111, Schramm, Georg ORCID: 0000-0002-2251-3195, Pietzsch, Jens ORCID: 0000-0002-1610-1493, Pietsch, Markus and Loeser, Reik (2016). Synthesis and Kinetic Characterisation of Water-Soluble Fluorogenic Acyl Donors for Transglutaminase 2. ChemBioChem, 17 (13). S. 1263 - 1282. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1439-7633

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Abstract

Small glutamate-containing peptides bearing coumarin derivatives as fluorescent leaving groups attached to the -carboxylic acid group of the Glu residue were synthesised and investigated with regard to their potential to act as substrates for transglutaminase2 (TGase2). 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 TGase2-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.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Wodtke, RobertUNSPECIFIEDorcid.org/0000-0001-7462-7111UNSPECIFIED
Schramm, GeorgUNSPECIFIEDorcid.org/0000-0002-2251-3195UNSPECIFIED
Pietzsch, JensUNSPECIFIEDorcid.org/0000-0002-1610-1493UNSPECIFIED
Pietsch, MarkusUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Loeser, ReikUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
URN: urn:nbn:de:hbz:38-270635
DOI: 10.1002/cbic.201600048
Journal or Publication Title: ChemBioChem
Volume: 17
Number: 13
Page Range: S. 1263 - 1282
Date: 2016
Publisher: WILEY-V C H VERLAG GMBH
Place of Publication: WEINHEIM
ISSN: 1439-7633
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
PIG LIVER TRANSGLUTAMINASE; TISSUE TRANSGLUTAMINASE; CELIAC-DISEASE; HUNTINGTONS-DISEASE; ASSAY; CELL; FLUORESCENCE; SUBSTRATE; MECHANISM; BINDINGMultiple languages
Biochemistry & Molecular Biology; Chemistry, MedicinalMultiple languages
Refereed: Yes
URI: http://kups.ub.uni-koeln.de/id/eprint/27063

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