Počet záznamů: 1
Synthesis of lucifensin by native chemical ligation and characteristics of its isomer having different disulfide bridge pattern
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SYSNO ASEP 0431796 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Synthesis of lucifensin by native chemical ligation and characteristics of its isomer having different disulfide bridge pattern Tvůrce(i) 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, ORCIDCelkový počet autorů 7 Zdroj.dok. Journal of Peptide Science - ISSN 1075-2617
Roč. 20, č. 9 (2014), s. 725-735Poč.str. 11 s. Jazyk dok. eng - angličtina Země vyd. GB - Velká Británie Klíč. slova lucifensin ; native chemical ligation ; solid-phase peptide synthesis ; antimicrobial activity ; CD spectroscopy ; DTT reduction Vědní obor RIV CE - Biochemie Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000340423800008 EID SCOPUS 84905979678 DOI 10.1002/psc.2663 Anotace 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. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Rok sběru 2015
Počet záznamů: 1