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Nucleic Acids Research, 1994, Vol. 22, No. 23 5128-5134
© 1994

STRUCTURAL BIOLOGY

Conformation, hydrogen bonding and aggregate formation of guanosine 5'-monophosphate and guanosine in dimethylsulfoxide

R. Ted West, Leoncio A. Garza, II, William R. Winchester+ and Judith A. Walmsely*

Division of Earth and Physical Sciences, The University of Texas at San Antonio San Antonio, TX 78249, USA +Department of chemistry, Trinity University San Antonio, TX 78212, USA

*To whom correspondence shoul be addressed

Received December 13, 1993. Revised June 24, 1994. Accepted June 24, 1994.

The tetrabutylammonium salt of guanosine 5'-monophosphate (5'-GMP) dissolves in DMSO-d6 forming aggregated species which exhibit some properties of reverse micelles. 1H NOESY experiments show that the 5'-GMP adopts the syn conformation about the glycosidic bond. Molecular mechanics calculations reveal a stable structure with this conformation in which the phosphate group and the amino group of the base are in close enough proximity to hydrogen bond. In contrast inosine 5'-monophosphate in DMSO-d6, which has no NH2 group for hydrogen bond stabilization of the syn conformation, is shown by NMR to have the anti structure. Guanosine in DMSO-d6 behaves differently from 5'-GMP. Guanosine adopts the anti conformation and forms a symmetric dimer via hydrogen bonding between the N3 and NH2 of the bases.


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