Toward synthesis of alpha-alkyl amino glycines (A3G), new amino acid surrogates.
A general method giving access to protected alpha-alkyl amino glycines (A3G) 4 from the previously described precursor alpha-isopropylthioglycine 1 is described. In the presence of N-bromosuccinimide, displacement of the thiol by a large variety of amines afforded the corresponding racemic amino acid mimics. The efficiency of the reaction was strongly dependent on the protective groups of the nucleophile used in the condensation.
Yaouancq
Loïc
L
Institut de Chimie des Substances Naturelles, CNRS-UPR2301, 91198 Gif-sur-Yvette, France.
René
Loïc
L
Tran Huu Dau
Marie-Elise
ME
Badet
Bernard
B
D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D005998:Glycine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D000588:Amines; D000596:Amino Acids; D005998:Glycine