INFLUENCE OF SUBSTITUENTS AT THE 5 POSITION ON THE STRUCTURE OF URIDINE
INFLUENCE OF SUBSTITUENTS AT THE 5 POSITION ON THE STRUCTURE OF URIDINE
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DOI：
10.1021/ja00531a007
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发表时间：
1980-01-01
影响因子：
15
通讯作者：
BOHM, MC
中科院分区：
文献类型：
--
作者：
EGERT, E;LINDNER, HJ;BOHM, MC
The conformations of 5-substituted uridines, some of which are found in the 1st anticodon position of tRNA, were studied by X-ray crystallography, 1H NMR spectroscopy and quantum-chemical methods. The electronic effect of a substituent X at the 5 position influences not only the base moiety, but also the N(1).sbd.C(1'') and C(1'').sbd.O(1'') bonds in opposite ways and the conformation of the ribose via the dihedral angle .chi. about the glycosidic bond. This can be rationalized in simple MO schemes using the concepts of "through-bond" and "through-space" interaction which result in an electron transfer from O(1'') to X. EH and MINDO/3 calculations suggest that the ribosyl moiety acts as a variable donor whose strength depends on .chi. and X. The favored .chi. values of C(2'')-endo- and C(3'')-endo-uridine predicted by MINDO/3 are in line with the experimental data.
