Figure 2: Chemoselective synthesis of phosphorothiolate esters peptides 4 and 5. | Nature Communications

Figure 2: Chemoselective synthesis of phosphorothiolate esters peptides 4 and 5.

From: Chemoselective synthesis and analysis of naturally occurring phosphorylated cysteine peptides

Figure 2

(a) Reaction of peptide 1a with Ellman's reagent and peptide 2a with 5 eq. phosphite esters 3a–e. (b) Overlap of UPLC traces of reaction mixture for peptide 2a and phosphite 3d after 16 h (black) and phosphite 3d starting material (magenta). Formation of the phosphorothiolate ester 4d after 16 h incubation with phosphite 3d in DMF at room temperature. Magenta asterisk shows the by-products of the phosphite 3d decomposition, which overlap with the reaction mixture UPLC trace for peptide 2a and phosphite 3d. (c) UPLC-UV trace after purification by semi-preparative HPLC of phosphorothiolate ester 4d. a.u., arbitrary unit; r.t., room temperature.

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