A Pair of New Enantiomeric Amides with DNA-cleaving Function

Abstract

Abstract: A number of small molecules have been shown to hydrolyze RNA as probes in RNA structure studies but very few reports have been found that small molecules can hydrolyze DNA. Previously we found that ser-his dipeptide could cut DNA probably via a hydrolytic mechanism,and also showed protein-cleaving activity. We have focused on developing additional small molecules with DNA cleavage activity and studying their mechanism in the cleavage. In the present study,we designed a pair of new enantiomeric serine/histamine amides,L-Ser-Hism and D-Ser-Hism. These two amides were synthesized by coupling of L- and D-serine with histamine,respectively,using the common DCC peptide synthesis method. Their function was assessed by the electrophoresis of DNA products,which were produced from the incubation of the amides with DNA. It was found that both of the amides were capable of cleaving DNA significantly at optimal pH=6.0——6.5,and that the isomer L-Ser-Hism showed a stronger cleavage function than the other isomer D-Ser-Hism. However,they could not cleave the protein BSA when the amides were tested in the protein cleavage experiment. These findings suggest the preferential DNA cleavage function of the amides.

Key words: Serine-histamine amide, DNA, Cleavage

CLC Number:

O61.29

TrendMD:

ZHU Chang-Jin, LU Yang, DU Hai-Lian, JIANG Yu-Yang, ZHAO Yu-Fen. A Pair of New Enantiomeric Amides with DNA-cleaving Function[J]. Chem. J. Chinese Universities, 2004, 25(6): 1065.

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