1071446-05-3Relevant articles and documents
Synthesis of lucifensin by native chemical ligation and characteristics of its isomer having different disulfide bridge pattern
Stanchev, Stancho,Zawada, Zbigniew,Monincová, Lenka,Bednárová, Lucie,Slaninová, Ji?ina,Fu?ík, Vladimír,?e?ovsky, Václav
, p. 725 - 735 (2014)
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. This method 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. Acetamidomethyl-deprotection 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 α-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. Copyright
Head-to-tail macrocyclization of cysteine-free peptides using an o-aminoanilide linker
Ohara, Takumi,Kaneda, Masato,Saito, Tomo,Fujii, Nobutaka,Ohno, Hiroaki,Oishi, Shinya
, p. 1283 - 1286 (2018)
A head-to-tail macrocyclization protocol for the preparation of cysteine-free cyclic peptides was investigated. The o-aminoanilide linker constructed in the peptide sequence by a standard Fmoc-based peptide synthesis procedure was subjected to nitrite-med
GLUCOSE SENSITIVE INSULINS AND USES THEREOF
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Page/Page column 31, (2020/04/25)
The present invention provides glucose sensitive insulin derivatives comprising a macrocycle, a glucose mimetic and human insulin or an analogue thereof, and their pharmaceutical use. Furthermore, the invention relates to pharmaceutical compositions compr
Hybrid phase ligation for efficient synthesis of histone proteins
Yu, Ruixuan R.,Mahto, Santosh K.,Justus, Kurt,Alexander, Mallory M.,Howard, Cecil J.,Ottesen, Jennifer J.
supporting information, p. 2603 - 2607 (2016/03/05)
We introduce a hybrid solid-solution phase ligation approach that combines the efficiency of solid phase ligation with solution phase ligation in the total synthesis of modified histone proteins. A two linker strategy allows analysis throughout work on the solid phase and maximizes yields through cleavage at an external Rink, while an internal HMBA linker allows the native carboxyl terminus for any protein sequence. We demonstrate this approach for two histone proteins: Triple-acetylated H4-K5ac, K12ac, K91ac and CENP-A-K124ac.
