Mj. Han et al., POLYNUCLEOTIDE ANALOGS .6. SYNTHESIS AND CHARACTERIZATION OF ALTERNATING COPOLYMERS OF MALEIC-ANHYDRIDE AND DIHYDROPYRAN CONTAINING GUANINEDERIVATIVES, Journal of polymer science. Part A, Polymer chemistry, 33(11), 1995, pp. 1829-1839
2-Amino-6-chloropurine was reacted with 2-(tosyloxymethyl)-2,3-dihydro
-2H-pyran to give 2-(2-amino-6-chloropurin-9-ylmethyl)-2,3 (3) and its
N-7-isomer (4), which were treated with 5% aqueous trimethylamine to
result in 2-(guanin-9-ylmethyl)-2,3-dihydro-2H-pyran (5) and its N-7-i
somer (6), respectively. (N-2-Acetylguanin-9-ylmethyl)-3,4-dihydro-2H-
pyran (7) and -(N-2-acetylguanin-7-ylmethyl)-3,4-dihydro-2Hpyran (8),
obtained by acetylation of compounds 5 and 6, were copolymerized with
maleic anhydride to give the alternating copolymers 9 and 10, and they
were hydrolyzed to result in l)tetrahydropyran-5,6-diyl}{1,2-dicarbox
yethlene}] (11) and )tetrahydropyran-5,6-diyl}{1,2-dicarboxyethylene}]
(12), respectively. Polymer 11 showed hypochromicity whereas 12 exhib
ited hyperchromicity in aqueous solutions. Polymers 11 and 12 in aqueo
us solutions showed very strong excimer fluorescence with the maximum
intensities at 432 and 446 nm, respectively, at room temperature. The
two polymers showed polyelectrolyte effects, e.g., very high GPC molec
ular weights as well as reduced viscosities at low concentrations in w
ater. Normal behavior was retained by addition of inorganic salts. Sod
ium salts of polymers 11 and 12 migrated to the anode by electrophores
is and both showed two bands. (C) 1995 John Wiley & Sons, Inc.