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Synthesis of lucifensin by native chemical ligation and characteristics of its isomer having different disulfide bridge pattern
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SYSNO ASEP 0431796 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis of lucifensin by native chemical ligation and characteristics of its isomer having different disulfide bridge pattern Author(s) Stanchev, Stancho (UOCHB-X) RID, ORCID
Zawada, Zbigniew (UOCHB-X) ORCID, RID
Monincová, Lenka (UOCHB-X)
Bednárová, Lucie (UOCHB-X) RID, ORCID
Slaninová, Jiřina (UOCHB-X)
Fučík, Vladimír (UOCHB-X) RID
Čeřovský, Václav (UOCHB-X) RID, ORCIDNumber of authors 7 Source Title Journal of Peptide Science - ISSN 1075-2617
Roč. 20, č. 9 (2014), s. 725-735Number of pages 11 s. Language eng - English Country GB - United Kingdom Keywords lucifensin ; native chemical ligation ; solid-phase peptide synthesis ; antimicrobial activity ; CD spectroscopy ; DTT reduction Subject RIV CE - Biochemistry Institutional support UOCHB-X - RVO:61388963 UT WOS 000340423800008 EID SCOPUS 84905979678 DOI 10.1002/psc.2663 Annotation The antimicrobial 40-amino-acid-peptide lucifensin was synthesized by native chemical ligation (NCL) using N-acylbenzimidazolinone (Nbz) as a linker group. NCL is a method in which a peptide bond between two discreet peptide chains is created. Thismethod has been applied to the synthesis of long peptides and proteins when solid-phase synthesis is imcompatible. Two models of ligation were developed: [15 + 25] Ala-Cys and [19 + 21] His-Cys. The [19 + 21] His-Cys method gives lower yield because of the lower stability of 18-peptide-His-Nbz-CONH2 peptide, as suggested by density functional theory calculation. Acetamidomethyldeprotection and subsequent oxidation of the ligated linear lucifensin gave a mixture of lucifensin isomers, which differed in the location of their disulfide bridges only. The dominant isomer showed unnatural pairing of cysteines [C1 - 6], [C3 - 5], and [C2 - 4], which limits its ability to form alpha-helical structure. The activity of isomeric lucifensin toward Bacillus subtilis, Staphylococcus aureus, and Micrococcus luteus was lower than that of the natural lucifensin. The desired product native lucifensin was prepared from this isomer using a one-pot reduction with dithiotreitol and subsequent air oxidation in slightly alkaline medium. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2015
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