The synthesis of di- and oligo(deoxyribonucleoside phosphorodithioates) by dithiaphospholane method

Article abstract of DOI:10.1016/S0040-4039(00)60831-6

Four dinucleoside phosphorodithioates: T(PS2)T (1a), d(C(PS2)C) (1b), d(A(PS2)A) (1c) and d(G(PS2)G) (1d) were synthesized by reacting solid support-bound nucleosides with nucleoside 5'-O-DMT-3'-O-(2-thio-1,3,2-dithiaphospholanes) (2a-d) in the presence of DBU. Pyrimidine pentamers and decamers, free from phosphorothioate contamination, were obtained by this method.

Full text of DOI:10.1016/S0040-4039(00)60831-6

7586
2
B
Z
Yii
0.76
0.78
0.79
0.61
88.6
80.0
50.4
74.4
124.m
124.349
120.7 ppm
was
(min)
3
3
2.
3.
10 ml
10
3
4.
5.
ml
a) and b)
0.4 ml
0.4 ml
3
3
b)
(16%)
6.

HO
16.49
11.83
97
Id
.
lb, B=Cyt
l
1.5
ill
(Iii) in 20 min.
series.
and
shows a PAGE mobility
to that
(slightly
tbe
its
by Trityl ON Trityl OFF
(ca 80%) to slightly
was
by PAGE (20%. TBE
the
(a 20%)
main
mobility than that of
A
Further experiments to improve
in
introduced to the manuscript. We thank
for

G.;
D.;
in
1.
A
1 0 9 -1 3 4 .
G.;
A.;
Y.-X.;
J .;
2.
0 .;
3.
4.
5.
6.
7.
8.
9.
J .;
A.;
J.;
J.;
M.H.
Lat.
N.;
D.G.
0.
Y.;
N.;
1 9 9 1 .4 7 ,
11.
J .;
R.
van
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
Mad.
M.H.
van Boom, J.H.
4 8 1 4 8 3 .
T.
C.B.
T.; lwai,
Ma, Y.-X.;
K.;
M.;
A.;
E.
18.7279-7286.
31,
Yau,
A.;
WJ .;
M.;
1991. 19,
22.
23.
24.
as
NMR
Fr.
gun 13
= 115.5 ppm
matrix. For
J.
MAT 95
la-d the
[M-H]
in
26.
27.
28.
Xy, Y.Z.;
of
Ch.; Tan, Z.K.; Gait, M.J.
have been recently
1989.17,
by
al.’
(Received in UK 3 August 1992)