ISSN 1070-4272. Russian Journal of Applied Chemistry, 2006, Vol. 79, No. 3, pp. 508!510. + Pleiades Publishing, Inc., 2006.
Original Russian Text + A.M. Gazaliev, O.A. Nurkenov, I.V. Kulakov, A.A. Ainabaev, D.V. Bessonov, 2006, published in Zhurnal Prikladnoi Khimii,
2006, Vol. 79, No. 3, pp. 517!519.
Synthesis and Fungicidal Activity
of Alkaloid-Containing Carbohydrates
A. M. Gazaliev, O. A. Nurkenov, I. V. Kulakov, A. A. Ainabaev, and D. V. Bessonov
Institute of Organic Synthesis and Coal Fuel Chemistry of Kazakhstan Republic, Limited Liability Company,
Received December 23, 2005
Abstract-N-Glycosylamines, triethylammonium salt of xylosyl- and glucosylbenzyldithiocarbamates, and
their derivatives containing fragments of alkaloids were synthesized; some of these substances exhibit
Among numerous substances comprising the en-
vironment, carbohydrates and their derivatives occupy
an extremely important place and have enormous sig-
nificance in technology and everyday human activity.
Carbohydrates in the form of various derivatives enter
into the cell composition of any living body, playing
the role of structural material, energy source, sub-
strates, and regulators of specific and biochemical
Modified derivatives of monosaccharides are of
great scientific and practical interest, since many of
these have pronounced biological activity with a wide
spectrum of effect. A number of derivatives of mono-
saccharides find wide use in medicine, e.g., as effec-
tive anticancer and antiviral agents . All this stimu-
lates an interest in synthetic chemistry of modification
In recent years, N-glycosylamides (N-glycosides)
find expanding application for synthesis of natural
glycopeptides, their analogs, and glycoconjugates
used in various biological studies. N-Glycosylamines
are considered as potential pharmaceuticals, since
introduction of carbohydrate group into a molecule
not only increases the solubility but in some cases
alters the biological effect as well .
We obtain a series of new carbohydrate-containing
derivatives based on xylose and glucose for sub-
sequent study of their reactivity and biological ac-
Condensation of D-xylose (1) and D-glucose (2)
with benzylamine was performed in alcoholic solution
under heating by the procedure described in :
where R is H (1, 3), CH
OH (2, 4).
The synthesized xyloxylbenzylamine (3) and glu-
cosylbenzylamine (4) are hygroscopic white crystal-
line substances darkening in air. Depending on the
synthesis conditions, N-glycosides can crystallize with
1 or 0.5 mol of water. When stored in a desiccator
, they become anhydrous.
The IR spectra of the compounds contain an ab-
sorption band at 891+ 7cm
, suggesting b-conforma-
tion at the anomeric center. Vibrations of the NH
group appear in the range 288032920 cm
out-of-plane bending modes of the CH group of
the aromatic ring, in the ranges 7453755 and 6953
. The IR spectra of 3 and 4 show that they
contain no C=N bonds, i.e., they are not Schiff bases.
According to published data , the absorption in