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Is maleic hydrazide a pyrimidine or purine analogue?

Abstract

MALEIC hydrazide (structure I, R1=R2=H) is well known in agriculture as a growth inhibitor, but its mechanism of action is uncertain. Its close structural resemblance to the pyrimidine base uracil (structure II, R1=R2=H) has led to the suggestion that it replaces uracil in the RNA molecule1,2, and although this theory is not universally accepted3, maleic hydrazide is known to be incorporated into RNA2. The crystal structure of maleic hydrazide has now been elucidated (a full report will be published elsewhere) and a model of the molecular structure as found in the crystal has been used in attempts to form base pairs with the nucleic acid bases. The geometrical criteria of hydrogen bond formation suggests that maleic hydrazide can be regarded as either a pyrimidine or a purine analogue.

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CRADWICK, P. Is maleic hydrazide a pyrimidine or purine analogue?. Nature 258, 774 (1975). https://doi.org/10.1038/258774a0

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