A highly effective and versatile glycosylation method is developed, which uses 3,5-dimethyl-4-(2′phenylethynylphenyl)phenyl (EPP) glycosides as donors and NIS/TMSOTf as promoter and proceeds via an unprecedented dearomative activation mechanism.

C-Glycosyl peptides/proteins are metabolically stable mimics of the native glycopeptides/proteins bearing O/N-glycosidic linkages, and are thus of great therapeutical potential. Herein, we disclose a protocol for the syntheses of vinyl C-glycosyl amino acids and peptides, employing a nickel-catalyzed reductive hydroglycosylation reaction of alkyne derivatives of amino acids and peptides with common glycosyl bromides. It accommodates a wide scope of the coupling partners, including complex oligosaccharide and peptide substrates. The resultant vinyl C-glycosyl amino acids and peptides, which bear common O/N-protecting groups, are amenable to further transformations, including elongation of the peptide and saccharide chains.

Tryptamine derivatives such as tryptamine and bacillamides were strong algicidal compounds promising in controlling harmful algae blooms, but their bioactivity and application researches were hindered by extremely low natural production rates. This study found an induced production of algicidal tryptamine derivatives by co-culture of marine Streptomyces with Bacillus mycoides, and optimised the culture method through changing important factors such as medium nutrition content, culture mode and pH value. The final established co-culture method used only 5 g yeast extracts and 5 g glycerol in 1 L 75% sea water, but got a yield of 14.9 mg/L N-acetyltryptamine, 2.8 mg/L N-propanoyltryptamine, 3.0 mg/L bacillamide A, 13.7 mg/L bacillamide B and 9.6 mg/L bacillamide C, which were all undetectable under normal culture conditions.