348
MATYUGINA et al.
N-(4-(N-Benzylamino)benzoyl)-2-aminoethyl
ACKNOWLEDGMENTS
phosphate. A solution of N-hydroxysuccineimide ester
of 4-(N-benzylamino)benzoic acid (162 mg, 0.5 mmol)
in DMF (4 ml), triethylamine (210 µl, 1.5 mmol), and
methylimidazole (47 µl, 0.55 mmol) were added to a
solution of aminoethyl phosphate (212 mg, 1.5 mmol)
in water (1 ml) and the reaction mixture was stirred for
3 h at room temperature. Organic solvents were evapo-
rated in a vacuum, and the residue was dissolved in
water (2 ml) and centrifuged. The solution was evapo-
rated up to a volume of 2 ml, loaded on a reverse-phase
LiChroprep RP-18 column (2 × 18 cm), and eluted with
0.01 M NH4HCO3. The target fractions were evapo-
rated, and the residue was dissolved in water (3 ml) and
lyophilized to give 45 mg (23%) of the product. UV
(H2O, pH 6, λmax, nm): 290 (ε 11500). 1H NMR (D2O):
7.65, 7.43, 7.37 and 6.83 (9 H, four m, aryl), 4.43 (2 H,
m, CH2-aryl), 4.13 (2 H, m, CH2O), 3.64 (2 H, m,
CH2N). 31P NMR (D2O): –1.3.
2,2-Diphenylethyl triphosphate (IVa) was
obtained by treatment of diphenylmethanol with POCl3
in triethyl phosphate followed by the addition of tribu-
tylammonium pyrophosphate similar to [6] to give 16%
of the product. UV (H2O, pH 6, λmax, nm): 258
(ε 540).1H NMR (D2O): 7.39 (8H, m, Ph), 7.27 (2H, m,
Ph), 4.55 (2 H, m, CH2é), 3.56 (1 H, t, J 6.6, CHCH2).
31P NMR (D2é): –9.25 (1 P, d, J 19.3, Pγ), –10.69 (1 P,
d, J 20.3, Pα), –22.43 (1 P, dd, Pβ).
The work was supported by the Russian Foundation
for Basic Research, project no. 06-04-48248, and Fede-
ral Program: Studies and Design in Foreground Direc-
tions of Development of Research and Technical Com-
plex of Russia (State contract no. 02.512.11.2237).
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RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY Vol. 35 No. 3 2009