288402-26-6Relevant articles and documents
Rapid and Selective Chemical Editing of Ribosomally Synthesized and Post-Translationally Modified Peptides (RiPPs) via CuII-Catalyzed β-Borylation of Dehydroamino Acids
de Vries, Reinder H.,Viel, Jakob H.,Kuipers, Oscar P.,Roelfes, Gerard
supporting information, p. 3946 - 3950 (2020/12/25)
We report the fast and selective chemical editing of ribosomally synthesized and post-translationally modified peptides (RiPPs) by β-borylation of dehydroalanine (Dha) residues. The thiopeptide thiostrepton was modified efficiently using CuII-catalysis under mild conditions and 1D/2D NMR of the purified product showed site-selective borylation of the terminal Dha residues. Using similar conditions, the thiopeptide nosiheptide, lanthipeptide nisin Z, and protein SUMO_G98Dha were also modified efficiently. Borylated thiostrepton showed an up to 84-fold increase in water solubility, and minimum inhibitory concentration (MIC) assays showed that antimicrobial activity was maintained in thiostrepton and nosiheptide. The introduced boronic-acid functionalities were shown to be valuable handles for chemical mutagenesis and in a reversible click reaction with triols for the pH-controlled labeling of RiPPs.
Synthesis method and application of 1-aza -5-germanium-5-alkyl bicyclic [3.3.3] undecane compound.
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Paragraph 0235; 0240, (2020/05/11)
The invention provides a 1-aza-5-germanium hetero-5-alkyl bicyclic [3.3.3] hendecane compound having a structure shown in the formula I, and the types of the 1-aza-5-germanium hetero-5-alkyl bicyclic[3.3.3] hendecane compound are expanded. The provided compound can serve as a nucleophilic reagent, the air and humidity conditions of the nucleophilic reagent are stable, and the efficiency of the Ge-Stille coupling reaction of aryl halogen and the 1-aza-5-germanium hetero-5-alkyl bicyclic [3.3.3] hendecane compound is high.
Industrial preparation method of lacosamide
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Paragraph 0018; 0021; 0022; 0027, (2018/03/26)
The invention relates to an industrial preparation method of lacosamide. Esterification is performed on D-serine for generating D-serine methyl ester hydrochloride; the D-serine methyl ester hydrochloride reacts with acetyl chloride for generating N-acetyl-D-serine methyl ester; the N-acetyl-D-serine methyl ester reacts with benzylamine for obtaining (R)-2-acetamido-N-benzyl-3-hydroxypropionamide;the (R)-2-acetamido-N-benzyl-3-hydroxypropionamide reacts with methyl p-toluenesulfonate under an alkaline condition for obtaining (R)-2-acetamido-N-benzyl-3-methoxypropionamide. The preparation method provide by the invention has relatively mild reaction conditions in each steps; the raw materials are easy to obtain; no high-toxicity reagent is used; a safe and environment-friendly green chemistry idea is met; and the method is suitable for industrial amplification.