Fluorescent Boronic Acid Compounds
FULL PAPER
HR ESI-MS: m/z calcd for C13H13BrNO: 278.0181 [M+H]+; found:
278.0190.
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N-[5-(5,5-Dimethyl-[1,3,2]dioxaboronan-2-yl)-naphthalen-1-yl]-N-methyl-
acetamide (13): Compound 13 was synthesized from 12 by following the
equivalent reaction procedure to that used for the synthesis of 9. The
crude product was purified on a silica gel column, with elution with
CH2Cl2/hexanes (2:1), to give compound 13 as a white powder (70%):
1H NMR (300 MHz, CDCl3): d=8.81 (d, J=8.7, 1H), 8.11 (d, J=6.9,
1H), 7.89 (d, J=8.4, 1H), 7.62–7.52 (m, 2H), 7.36 (d, J=7.2, 2H), 3.94
(s, 4H), 3.38 (s, 3H), 1.78 (s, 3H), 1.15 ppm (s, 6H); 13C NMR (100 MHz,
CD3OD): d=171.5, 140.8, 137.9, 135.0, 130.0, 129.1, 128.6, 126.6, 125.8,
124.7, 122.2 ppm; EI-MS: m/z calcd for C18H22BNO3: 311.2 [M+]; found:
311.0.
5-(Acetyl-methylamino)-naphthalene-1-boronic acid (5-AMANBA, 4):
Compound 4 was synthesized from 15 by following the same deprotection
procedure as that used for the synthesis of 1. The crude product was puri-
fied on a silica gel column, with elution with CH2Cl2/MeOH (30:1), to
give 4 as a white powder (45%): 1H NMR (300 MHz, CDOD3): d=7.92
(d, J=8.1, 1H), 7.78 (d, J=3.6, 1H), 7.64 (m, 3H), 7.50 (d, J=6.6, 1H),
4.87 (s, 2H), 3.30 (s, 3H), 1.73 ppm (s, 3H); 13C NMR (100 MHz,
CD3OD): d=173.7, 141.9, 137.6, 132.1, 130.7, 130.1, 128.1, 127.2, 126.4,
123.7 ppm; HR ESI-MS: m/z calcd for C13H15BNO3: 244.1145 [M+H]+;
found: 244.1146.
Procedures for the binding studies: Distinct solutions of the sensors and
the sugars (various concentrations) were prepared in 0.1m phosphate
buffer at pH 7.40. Then, a sensor solution (2 mL) was mixed with a sugar
solution (2 mL). After stirring for 20 min, the mixture was transferred
into a 1-cm quartz cuvette and the fluorescence intensity was recorded
immediately.
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Acknowledgements
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Financial support from the National Institutes of Health (Grant nos.:
CA88343, CA113917, and NO1-CO-27184), the Georgia Cancer Coali-
tion 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 acknowledged.
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