Synthesis of N-arylsulfonyl dl-phenylserine derivatives exhibiting anti-inflammatory activity in experimental studies

Exploring the Scope of an α/β-Aminomutase for the Amination of Cinnamate Epoxides to Arylserines and Arylisoserines

“…18 (2S,3R)-3,4-Dihydroxyphenylserine (DOPS, Droxidopa) is used for hypotension and as a Parkinsonian therapeutic, 19−21 while N-arylsulfonyl derivatives of phenylserine ethyl esters function as nonsteroidal anti-inflammatory drugs. 22 β-Hydroxy-α-amino acids have also been used recently in protein synthesis by chemical ligation at N-terminal serine and threonine sites, and this technique can likely be expanded to incorporate other nonproteinogenic β-hydroxy-amino acids. 23 Additionally, an interesting subclass of non-natural heterocyclic β-hydroxy-α-amino acid amides are drug leads for their analgesic and immunostimulant activities.…”

“…Incorporation of unique stereochemistry into the residues of peptide chains can change their properties by, for example, increasing the stability against peptidases and prolonging bioavailability. − Further, β-hydroxy-α-amino acid scaffolds (Figure ) are found in clinically important antibiotics, including glycopeptide vancomycin and its analogues, ristocetin from Amycolatopsis , and teicoplanins from Actinoplanes, the phenylpropanoid chloramphenicol from Streptomyces, and katanosin depsipeptides from Cytophaga and Lysobacter bacteria. , The pentapeptide gymnangiamide from marinehydroid Gymnangium regae shows anticancer activity . (2 S ,3 R )-3,4-Dihydroxyphenylserine (DOPS, Droxidopa) is used for hypotension and as a Parkinsonian therapeutic, − while N -arylsulfonyl derivatives of phenylserine ethyl esters function as nonsteroidal anti-inflammatory drugs . β-Hydroxy-α-amino acids have also been used recently in protein synthesis by chemical ligation at N-terminal serine and threonine sites, and this technique can likely be expanded to incorporate other nonproteinogenic β-hydroxy-amino acids .…”