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Hydrogen bond catalysis of mononucleotide ethylation supports non-random DNA alkylations by N-ethyl, N-nitrosourea

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Summary

The axial (ax.) and equatorial (eq.) diastereomeric forms of phosphate triesters resulting from reactions of N-ethyl, N-nitrosourea with 3 cyclic mononucleotides were analyzed by column liquid chromatography (CLC). Evidence is presented that the 2′OH group of 3′, 5′cAMP essentially contributes to the stereoselective eq. alkyl substitution, most probably by hydrogen bonding catalysis. The neighboring group direction of ethylation gives substantial support to non-random DNA alkylations by NEU.

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Authors and Affiliations

  1. Zentrum Biochemie, Hannover School of Medicine, D-3000, Hannover 61, Germany

    K. -W. Stahl & F. E. Köster

Authors
  1. K. -W. Stahl
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  2. F. E. Köster
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Additional information

We acknowledge the helpful cooperation of Dr Fritz Eckstein, M.P.I. for Exp. Medicine, Göttingen, who determined the31P-N.M.R. spectra of the diastereomeric forms of the neutral ethylester of 3′, 5′ cAMP. This work has been supported by a personal grant to one of us (Sta 131/6 PAN) from the Deutsche Forschungsgemeinschaft. Reprint requests to K.-W. Stahl.

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Stahl, K.W., Köster, F.E. Hydrogen bond catalysis of mononucleotide ethylation supports non-random DNA alkylations by N-ethyl, N-nitrosourea. Experientia 40, 734–736 (1984). https://doi.org/10.1007/BF01949749

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  • DOI: https://doi.org/10.1007/BF01949749

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