One-pot chemical pyro- and tri-phosphorylation of peptides by using diamidophosphate in water

Abstract

Protein (pyro)phosphorylation is emerging as a post-translational modification (PTM) in signalling pathways involved in many cellular processes. However, access to synthetic pyrophosphopeptides that can serve as tools for understanding protein...

Enhancing Prebiotic Phosphorylation and Modulating the Regioselectivity of Nucleosides with Diamidophosphate

“…The observations reported above, along with previous works, ,, create a scenario where DAP-mediated phosphorylation could potentially enable a continuous transition starting from nucleosides to oligonucleotides, helped by various small molecules, some of which also have the potential to give rise to efficient catalysts. Implicit in this scenario is the intriguing possibility of side-by-side formation and coevolution of peptides and oligonucleotides by DAP-mediated phosphorylation chemistry.…”

“…9,10 Thus, DAP-mediated phosphorylation with 2aminoimidazole could provide a model scenario for starting from the (a) phosphorylation of nucleosides to form mononucleotides, (b) activation of mononucleotides for use by ribozymes for ligation, and (c) conversion of mononucleotides to nucleoside-triphosphates (NTPs), which are the substrates used in extant biology. 54,55 The observations reported above, along with previous works, 5,55,56 create a scenario where DAP-mediated phosphorylation could potentially enable a continuous transition starting from nucleosides to oligonucleotides, helped by various small molecules, some of which also have the potential to give rise to efficient catalysts. Implicit in this scenario is the intriguing possibility of side-by-side formation and coevolution of peptides and oligonucleotides by DAP-mediated phosphorylation chemistry.…”

Towards a prebiotic chemoton – nucleotide precursor synthesis driven by the autocatalytic formose reaction

“…63 DAP has been shown to phosphorylate a wide variety of biological building blocks including nucleo(s/t)ides, amino acids, and lipid precursors under mild conditions. [64][65][66][67] Another issue is the fact that that under the experimental conditions tested herein, 2-NH 2 Ox does not contribute signicantly to tetrose and pentose aminooxazoline synthesis. This observation was attributed mechanistically to the relative instability of glycolaldehyde and glyceraldehyde, which more rapidly undergo aldol additions instead of cycloaddition with 2-NH 2 Ox under alkaline pH.…”

“…63 DAP has been shown to phosphorylate a wide variety of biological building blocks including nucleo(s/t)ides, amino acids, and lipid precursors under mild conditions. 64–67…”

Enhancing activity of food protein‐derived peptides: An overview of pretreatment, preparation, and modification methods

“…In the postphosphorylation approach, a phosphoramidite reagent is utilized to selectively phosphorylate the hydroxyl group of Ser, Tyr, or Thr residues in a fully synthesized peptide. The phosphorylation reaction is carried out in the presence of a catalyst and an activator, after which the phosphorylated peptide is cleaved from the resin and purified (Lin, Leman, et al., 2022). Conversely, in the monomeric approach, a phosphorylated amino acid is directly incorporated into the peptide sequence during synthesis as a protected monomer.…”