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ing group. This is because the deprotection does not
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2
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has the following desirable characteristics: (1) easy and
high yield protection, (2) stable under normal handling
conditions, (3) easy cleavage under mild oxidative condi-
tions, and (4) works with arylboronic acids with either
an electron-withdrawing or electron-donating group. It
is worth noting that the protecting group has a chiral
center and is in the racemic form. Therefore, in the pro-
tection of a boronic acid with an existing chiral center,
diasteroisomers are expected.
2
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Acknowledgements
Financial support from the National Institutes of Health
(
CA88343, CA113917, and NO1-CO-27184), the Geor-
3
727–3730; (r) Badugu, R.; Lakowicz, J. R.; Geddes, C. D.
gia Cancer Coalition through a Distinguished Cancer
Scientist Award, and the Georgia Research Alliance
through an Eminent Scholar endowment and an Emi-
nent Scholar Challenge grant is gratefully acknowl-
edged. Some free samples of boronic acid from
Frontier Scientific are also gratefully acknowledged.
Bioorg. Med. Chem. 2005, 13, 113–119; (s) Hoeg-Jensen,
T.; Havelund, S.; Nielsen, P. K.; Markussen, J. J. Am.
Chem. Soc. 2005, 127, 6158–6159.
. For papers on factors affecting the binding, see: (a)
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300; Yan, J.; Springsteen, G.; Deeter, S.; Wang, B.
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Supplementary data
Supplementary data are available with this paper includ-
ing experimental procedures and spectroscopic data for
all new compounds. Supplementary data associated with
7
1
93; Springsteen, G.; Wang, B. Chem. Commun. 2001,
608–1609; Karnati, V. V.; Gao, X.; Gao, S.; Yang, W.;
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