Chemical methods for N- and O-sulfation of small molecules, amino acids and peptides.

Chemical methods for N- and O-sulfation of small molecules, amino acids and peptides. Chembiochem. 2019 Nov 06;: Authors: Benedetti AM, Gill DM, Tsang CW, Jones AM Abstract Sulfation of the amino acid residues of proteins is an emerging post-translational modification, the functions of which are yet to be fully understood. Current sulfation methods are limited mainly to O -tyrosine (sY) which requires negatively charged species around the desired amino acid residue and a specific sulfotransferase enzyme. Alternatively, for solid phase peptide synthesis a de novo protected sY is required. Therefore, synthetic routes are required to go beyond O -sulfation. We have developed a novel route to N -sulfamation and can dial-in/out O -sulfation (without S -sulfurothiolation), mimicking the initiation step of the ping-pong sulfation mechanism identified in structural biology. This rapid, low temperature and non-racemizing method is applicable to a range of amines, amides, amino acids, and peptide sequences. PMID: 31692230 [PubMed - as supplied by publisher]
Source: Chembiochem - Category: Biochemistry Authors: Tags: Chembiochem Source Type: research