The Role of the Amino Protecting Group during Parahydrogenation of Protected Dehydroamino Acids.
A series of dehydroamino acids endowed with different protective groups at the amino and carboxylate moieties and with different substituents at the double bond have been reacted with parahydrogen. The observed ParaHydrogen Induced Polarization (PHIP) effects in the (1)H NMR spectra are strongly dependent on the amino protecting group. DFT calculations allowed us to establish a relationship between the structures of the reaction intermediates (whose energies depend on the amido substitution) and the observed PHIP patterns.
Department of Molecular Biotechnologies and Health Sciences, University of Torino , Via Nizza 52, 10126 Torino, Italy.
Erika
E
Cerutti
Department of Molecular Biotechnologies and Health Sciences, University of Torino , Via Nizza 52, 10126 Torino, Italy.
Alessandra
A
Viale
Department of Molecular Biotechnologies and Health Sciences, University of Torino , Via Nizza 52, 10126 Torino, Italy.
Carlo
C
Nervi
Department of Molecular Biotechnologies and Health Sciences, University of Torino , Via Nizza 52, 10126 Torino, Italy.
Roberto
R
Gobetto
Department of Molecular Biotechnologies and Health Sciences, University of Torino , Via Nizza 52, 10126 Torino, Italy.
Silvio
S
Aime
D000596:Amino Acids / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D006865:Hydrogenation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D020011:Protective Agents / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
D000596:Amino Acids; D020011:Protective Agents; D012997:Solvents; D006859:Hydrogen