The Role of the Amino Protecting Group during Parahydrogenation of Protected Dehydroamino Acids | Zendy

Erika Cerutti | Zendy; Alessandra Viale | Zendy; Carlo Nervi | Zendy; Roberto Gobetto | Zendy; Silvio Aime | Zendy

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The Role of the Amino Protecting Group during Parahydrogenation of Protected Dehydroamino Acids

Author(s) -

Erika Cerutti,

Alessandra Viale,

Carlo Nervi,

Roberto Gobetto,

Silvio Aime

Publication year - 2015

Publication title -

the journal of physical chemistry a

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.756

H-Index - 235

eISSN - 1520-5215

pISSN - 1089-5639

DOI - 10.1021/acs.jpca.5b06802

Subject(s) - group (periodic table) , amino acid , protecting group , chemistry , biochemistry , organic chemistry , alkyl

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.

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