HOW DOES THE STERIC EFFECT DRIVE THE SUGAR CONFORMATION IN THE 3'-C-BRANCHED NUCLEOSIDES

被引：43

作者：

PLAVEC, J ^{[1
]}

GARG, N ^{[1
]}

CHATTOPADHYAYA, J ^{[1
]}

机构：

[1] UNIV UPPSALA,CTR BIOMED,DEPT BIOORGAN CHEM,BOX 581,S-75123 UPPSALA,SWEDEN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 12期

关键词：

D O I：

10.1039/c39930001011

中图分类号：

O6 [化学];

学科分类号：

0703 [化学];

摘要：

The steric effect of 3'-CH2OH group drives the North reversible South pseudorotational equilibrium of the sugar moiety in the isomeric 1-(2',3'-dideoxy-3'-hydroxymethyl-beta-D-erythro-pentofuranosyl)cytosine 1 (80% North at 298 K; DELTAH-degrees = +5.9 kJ mol-1, DELTAS-degrees = +7.4 J K-1 mol-1), and 1-(2',3'-dideoxy-3'-hydroxymethyl-beta-D-threo-pentofuranosyl)cytosine 2 (82% South at 293 K; DELTAH-degrees = -0.9 kJ mol-1, DELTAS-degrees = +9.5 J K-1 mol-1) and it is found to be three times stronger in 2 (DELTAH-degrees = -5.9 kJ mol-1) in comparison with that of 1 (DELTAH-degrees = -2.1 kJ mol-1).

引用

页码：1011 / 1014

页数：4

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