Open AccessDepyrimidination of synthetic poly(uridylic acid) analogue
Author(s) -
Han Man Jung,
Cho Tae Joon,
Kim Ki Ho,
Yoo Kyung Soo,
Park Young Dong,
Chang Ji Young
Publication year - 2000
Publication title -
journal of polymer science part a: polymer chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.768
H-Index - 152
eISSN - 1099-0518
pISSN - 0887-624X
DOI - 10.1002/(sici)1099-0518(20000201)38:3<423::aid-pola5>3.0.co;2-r
Subject(s) - chemistry , hydrolysis , uracil , copolymer , polymer , maleic acid , nucleic acid , maleic anhydride , polymer chemistry , glycosidic bond , nucleoside , reaction rate constant , activation energy , dna , kinetics , organic chemistry , stereochemistry , biochemistry , physics , quantum mechanics , enzyme
A poly(uridylic acid) analogue, poly{[1′‐(β‐uracil‐1‐yl)‐5′‐deoxy‐D‐ erythro ‐pent‐4′‐enofuranose]‐ alt ‐[maleic acid]} (3), was synthesized by the alternating copolymerization of nucleoside derivative 1 and maleic anhydride and subsequent hydrolysis. N ‐glycosidic bonds of the polymer were hydrolyzed spontaneously to liberate uracil from the polymer backbone in a buffer solution (pH 7.4) at room temperature. The depyrimidination rate constant of the polymer at pH 7.4 at 80 °C was 8.2 × 10 −5 s −1 , which was 10 4 times higher than that of the depyrimidination of DNA (1.2 × 10 −9 s −1 ) under the same condition. The activation energy for the depyrimidination was 16 kcal/mol, which was about half of that for the relevant nucleoside reactions. The increase in the depyrimidination rate was attributable to the high potential energy of the polymer caused by the crowded environment around the bases, so that the polymer was more susceptible to the hydrolysis. Because natural nucleic acids often have compact structures with a crowded environment around the bases by an intricate chain folding, the pyrimidination also may have been accelerated in a similar manner in the biological system. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 423–429, 2000