Synthesis and Electron
Spin Relaxation of Tetracarboxylate
Pyrroline Nitroxides
Version 2 2017-06-19, 20:15
Version 1 2017-01-13, 20:44
Posted on 2017-06-19 - 20:15
We report the design,
synthesis, and electron spin relaxation properties
of hydrophilic tetracarboxylate ester pyrroline nitroxides 1 and 2, which serve as models in the search for new
spin labels for DEER distance measurement at room temperature. The
nitroxides are designed to have the methyl groups further away from
the N–O spin site to decrease the inequivalent couplings of
the unpaired electron to the methyl protons that shorten Tm at T > 70 K in currently used labels.
The key step in the synthesis of 1 and 2 is the reaction of the dianion of pyrrole-1,2,5-tricarboxylic acid tert-butyl ester dimethyl ester with electrophiles such
as methyl chloroformate and methyl bromoacetate. Structures of 1 and 2 are confirmed by X-ray crystallography.
Studies of electron spin relaxation rates in rigid trehalose/sucrose
matrices reveal approximately temperature independent values of 1/Tm for 1 and 2 up to
about 160 K and modest temperature dependence up to 295 K, demonstrating
that increasing the distance between the nitroxide moiety and methyl
groups is effective in lengthening Tm at T > 70 K.
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Huang, Shengdian; Paletta, Joseph T.; Elajaili, Hanan; Huber, Kirby; Pink, Maren; Rajca, Suchada; et al. (2017). Synthesis and Electron
Spin Relaxation of Tetracarboxylate
Pyrroline Nitroxides. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.6b02737
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AUTHORS (9)
SH
Shengdian Huang
JP
Joseph T. Paletta
HE
Hanan Elajaili
KH
Kirby Huber
MP
Maren Pink
SR
Suchada Rajca
GE
Gareth R. Eaton
SE
Sandra S. Eaton
AR
Andrzej Rajca