Synthesis of Unnatural Amino Acids Functionalized with Sterically Shielded Pyrroline Nitroxides | Zendy

Ying Wang | Zendy; Joseph T. Paletta | Zendy; Kathleen E. Berg | Zendy; Erin Reinhart | Zendy; Suchada Rajca | Zendy; Andrzej Rajca | Zendy

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Synthesis of Unnatural Amino Acids Functionalized with Sterically Shielded Pyrroline Nitroxides

Author(s) -

Ying Wang,

Joseph T. Paletta,

Kathleen E. Berg,

Erin Reinhart,

Suchada Rajca,

Andrzej Rajca

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol502449r

Subject(s) - pyrroline , chemistry , steric effects , pyrrolidine , nitroxide mediated radical polymerization , cysteine , amino acid , glutathione , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , enzyme , radical polymerization , copolymer , polymer

A series of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides were synthesized. Their reduction by ascorbate/glutathione indicates that L-cysteine functionalized with gem-diethylpyrroline nitroxide is reduced at the slowest rate and is comparable to that measured for the most resistant to reduction pyrroline and pyrrolidine nitroxides.

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