Glycine-selective α-carbon-nitrogen bond cleavage of dipeptides by nickel peroxide
CJ Easton, SK Eichinger, MJ Pitt
Index: Easton, Christopher J.; Eichinger, Sharon K.; Pitt, Michael J. Tetrahedron, 1997 , vol. 53, # 15 p. 5609 - 5616
Full Text: HTML
Citation Number: 25
Abstract
Nickel peroxide selectively cleaves the α-carbon-nitrogen bond of glycine residues in dipeptide derivatives to give the corresponding amides. The glycine selectivity is attributable to preferential complexation of the reactant residue to nickel peroxide and subsequent reaction via a stable α-centred glycyl radical. The oxidation process serves as a chemical model for peptidylglycine α-amidating monooxygenase (PAM) and, in addition, may have ...
Related Articles:
Photochemical and thermal reactions of 2-aryloxybenzohydroxamic acids
[Das, Vijay Kumar; Devi, Rashmi Rekha; Thakur, Ashim Jyoti Applied Catalysis A: General, 2013 , vol. 456, p. 118 - 125]
Electrochemical synthesis of amides: direct transformation of methyl ketones with formamides
[Huang, Haolai; Yuan, Gaoqing; Li, Xianwei; Jiang, Huanfeng Tetrahedron Letters, 2013 , vol. 54, # 52 p. 7156 - 7159]
[Zhang, Nana; Li, Binyao; Zhong, Hongban; Huang, Jianhui Organic and Biomolecular Chemistry, 2012 , vol. 10, # 47 p. 9429 - 9439]
[Friestad, Gregory K.; Ji, An Organic Letters, 2008 , vol. 10, # 11 p. 2311 - 2313]
[Friestad, Gregory K.; Ji, An Organic Letters, 2008 , vol. 10, # 11 p. 2311 - 2313]