Universität zu Köln

Heimer, Pascal, Tietze, Alesia A., Boehm, Miriam, Giernoth, Ralf ORCID: 0000-0003-2282-6586, Kuchenbuch, Andrea, Stark, Annegret ORCID: 0000-0001-9547-3422, Leipold, Enrico, Heinemann, Stefan H. ORCID: 0000-0002-4144-0251, Kandt, Christian and Imhof, Diana ORCID: 0000-0003-4163-7334 (2014). Application of Room-Temperature Aprotic and Protic Ionic Liquids for Oxidative Folding of Cysteine-Rich Peptides. ChemBioChem, 15 (18). S. 2754 - 2766. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1439-7633

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Abstract

The oxidation of the conotoxin mu-SIIIA in different ionic liquids was investigated, and the results were compared with those obtained in [C(2)mim][OAc]. Conversion of the reduced precursor into the oxidized product was observed in the protic ILs methyl-and ethylammonium formate (MAF and EAf, respectively), whereas choline dihydrogenphosphate and Ammoeng 110 failed to yield folded peptide. However, the quality and yield of the peptide obtained in MAF and EAF were lower than in the case of the product from [C(2)mim][OAc]. Reaction conditions (temperature, water content) also had an impact on peptide conversion. A closer look at the activities of mu-SIIIA versions derived from an up-scaled synthesis in [C(2)mim][OAc] revealed a significant loss of the effect on ion channel Na(V)1.4 relative to the buffer-oxidized peptide, whereas digestion of either mu-SIIIA product by trypsin was unaffected. This was attributed to adherence of ions from the IL to the peptide, because the disulfide connectivity is basically the same for the differentially oxidized mu-SIIIA versions.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Heimer, Pascal UNSPECIFIED UNSPECIFIED UNSPECIFIED Tietze, Alesia A. UNSPECIFIED UNSPECIFIED UNSPECIFIED Boehm, Miriam UNSPECIFIED UNSPECIFIED UNSPECIFIED Giernoth, Ralf UNSPECIFIED orcid.org/0000-0003-2282-6586 UNSPECIFIED Kuchenbuch, Andrea UNSPECIFIED UNSPECIFIED UNSPECIFIED Stark, Annegret UNSPECIFIED orcid.org/0000-0001-9547-3422 UNSPECIFIED Leipold, Enrico UNSPECIFIED UNSPECIFIED UNSPECIFIED Heinemann, Stefan H. UNSPECIFIED orcid.org/0000-0002-4144-0251 UNSPECIFIED Kandt, Christian UNSPECIFIED UNSPECIFIED UNSPECIFIED Imhof, Diana UNSPECIFIED orcid.org/0000-0003-4163-7334 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-420239
DOI:	10.1002/cbic.201402356
Journal or Publication Title:	ChemBioChem
Volume:	15
Number:	18
Page Range:	S. 2754 - 2766
Date:	2014
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1439-7633
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language GROUND-STATE DYNAMICS; PARTICLE MESH EWALD; MU-CONOTOXIN PIIIA; MOLECULAR-DYNAMICS; SODIUM-CHANNELS; ALPHA-CHYMOTRYPSIN; ORGANIC-SYNTHESIS; HYDROGEN-BONDS; PROTEIN; BIOCATALYSIS Multiple languages Biochemistry & Molecular Biology; Chemistry, Medicinal Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/42023