Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent was written by Wadzinski, Tyler J.;Steinauer, Angela;Hie, Liana;Pelletier, Guillaume;Schepartz, Alanna;Miller, Scott J.. And the article was included in Nature Chemistry in 2018.Category: ethers-buliding-blocks The following contents are mentioned in the article:
Glycosylated natural products and synthetic glycopeptides represent a significant and growing source of biochem. probes and therapeutic agents. However, methods that enable the aqueous glycosylation of endogenous amino acid functionality in peptides without the use of protecting groups are scarce. Here, we report a transformation that facilitates the efficient aqueous O-glycosylation of phenolic functionality in a wide range of small mols., unprotected tyrosine, and tyrosine residues embedded within a range of complex, fully unprotected peptides. The transformation, which uses glycosyl fluoride donors and is promoted by Ca(OH)2, proceeds rapidly at room temperature in water, with good yields and selective formation of unique anomeric products depending on the stereochem. of the glycosyl donor. High functional group tolerance is observed, and the phenol glycosylation occurs selectively in the presence of virtually all side chains of the proteinogenic amino acids with the singular exception of Cys. This method offers a highly selective, efficient, and operationally simple approach for the protecting-group-free synthesis of O-aryl glycosides and Tyr-O-glycosylated peptides in water. This study involved multiple reactions and reactants, such as 4-Benzyloxyphenol (cas: 103-16-2Category: ethers-buliding-blocks).
4-Benzyloxyphenol (cas: 103-16-2) belongs to ethers. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Category: ethers-buliding-blocks
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem