Formation of pyrazine derivatives from D-glucosamine and their deoxyribonucleic acid(DNA) strand breakage activity.

Abstract

Two pyrazine derivatives [fructosazine (3) and deoxyfructosazine (6)] were simultaneously formed in a solution of D-glucosamine hydrochloride under various conditions. They showed deoxyribonucleic acid (DNA) strand breakage activity in plasmid pBR322 comparable to that of D-glucosamine. The DNA strand breakage by fructosazine (3) was stimulated by Cu2+.

Reduction Mechanism of Tetrazolium Salt XTT by a Glucosamine Derivative

“…These data coincide with those of deoxyfructosazine (Fig. 5) described by Sumoto et al, 10) except for the assignment of H-2? and H-2!.…”

“…Although the formation of glucosamine derivative has already been reported, 5,9,10) no systematic investigation on the formation mechanism has previously been made. To clarify the relationship between fraction D and other intermediate products, fraction D was again incubated at 379 C, and the XTT reducibility and HPLC pattern of the incubated solution were examined (Fig.…”

“…It has been reported that dihydrofructosazine showed DNA-breaking activity by the generation of active oxygen and a carbon-centered radical. 5,7,10) Therefore, the XTT assay, which can detect dihydrofructosazine, can be employed for evaluating the DNA-breaking activity of glucosamine. Since amino sugars such as mannosamine and galactosamine, apart from glucosamine described here, have shown DNA-breaking activity in the same manner and the XTT reducibility, 8,[10][11][12] the dihydrofructosazine type of compound could also be involved in the reduction of XTT with those amino sugars.…”

Synthesis, chemistry and applications of 5-hydroxymethyl-furfural and its derivatives

“…The reaction was carried out in benzene for 8 hours at 80 °C and led to HMF in 92% yield. The reaction of 2-amino-D-2-deoxyglucose hydrochloride 61 was carried out in mixed solvents with a tellurium buffer at 130°C for 4½ hours and led to 5-hydroxymethylfurfural. Grin et al 62 studied the conversion of fructose without a solvent leading to HMF.…”

Synthesis and DNA Strand Breakage Activity of Some 1,4-Diazepines.

“…Recently, we reported [2][3][4][5] that some pyrazine-related derivatives and other heterocyclic compounds derived from the reaction of 2,3-butanedione with ethylenediamine derivatives show significant DNA strand breakage activities.…”