Green synthesis of α,β- and β,β-dipeptides under solvent-free conditions.
The reactivity of N-tert-butyloxycarbonyl-N-carboxyanhydrides derived from β-alanine, (S)-β(3)-homophenylglycine, and (S)-β(3)-carboxyhomoglycine with different α- and β-amino ester hydrochlorides was examined under ball-milling activation. In particular, good to excellent yields of several relevant α,β- and β,β-dipeptides were obtained. An illustrative application of this methodology consisted in the high-yield synthesis of the mammalian α,β-dipeptide N-Boc-l-carnosine-OMe.
Hernández
José G
JG
Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado Postal 14-740, 07000, México, D.F., México.
Juaristi
Eusebio
E
D000409:Alanine / Q000737:chemistry; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D004952:Esters; D005998:Glycine / Q000737:chemistry; D055772:Green Chemistry Technology / Q000379:methods*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D004151:Dipeptides; D004952:Esters; D000409:Alanine; D005998:Glycine