869566-89-2

Upstream product

• 78359-00-9 4-(iodomethyl)-2-phenyl-1,3-thiazole 
• 4771-31-7 2-phenyl-4-chloromethylthiazole 
• 2227-79-4 benzenecarbothioamide 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1580457-16-4 tert-butyl N-[(2S)-1-[(2S,4S)-2-cyano-4-fluoropyrrolidin-1-yl]-1-oxo-3-(2-phenylthiazol-4-yl)propan-2-yl]carbamate 
• 1580456-74-1 (2S,4S)-1-[(2S)-2-amino-3-(2-phenylthiazol-4-yl)propanoyl]-4-fluoropyrrolidine-2-carbonitrile 

Relevant academic research and scientific papers

Stereoselective Synthesis of β-(5-Arylthiazolyl) α-Amino Acids and Use in Neurotensin Analogues

A series of new unnatural amino acids bearing a β-arylthiazole side chain was synthesized by exploiting a diastereoselective alkylation starting from glycine tert-butyl ester Schiff base with hydroxypinanone as the chiral inducer. This strategy afforded β-arylthiazole alanines in good chemical yields and with 98 % ee. Due to their aromatic properties, these newly generated amino acids were used to prepare neurotensin (NT)[8-13] analogues by serving as replacements for the native Tyr11 residue. Incorporation of the (L)-(+)-(β-phenylthiazol-4-yl)alanine residue at NT[8-13] position 11 improved plasma stability and selectivity towards NTS1, while also preserving native receptor binding affinity and biological activity. New β-arylthiazole alanines were synthesized in good chemical yields and with 98 % ee using a diastereoselective alkylation; these alanine derivatives were then used as Tyr11 replacements in the construction of neurotensin (NT)[8-13] analogues. The new NT analogues showed improved plasma stability and selectivity towards NTS1 thus preserving the hypotensive properties of the native peptide.