Studies on heterobifunctional cross-linking reagents, 6-maleimidohexanoic acid active esters.

Shinya Kida, Mitsuko Maeda, Keiko Hojo, Yusuke Eto, Shinsaku Nakagawa, Koichi Kawasaki

Index: Chem. Pharm. Bull. 55 , 685-687, (2007)

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Abstract

6-maleimidohexanoic acid N-hydroxysuccinimide ester has been used widely for preparation of enzyme immunoconjugates as a unique heterobifunctional cross-linking reagent. Its heterobifunctional reactivity is good, but its ester portion hydrolyzes easily in the presence of water. Several 6-maleimidohexanoic acid active esters (6-maleimidohexanoic acid 4-nitrophenyl ester, 6-maleimidohexanoic acid N-hydroxy-5-norbornene-endo-2,3-dicarboximide ester, and 6-maleimidohexanoic acid pentafluorophenyl ester) were prepared and their reactivity and stability in an aqueous media were tested. Of the synthetic esters, the pentafluorophenyl ester exhibited the highest reactivity and stability in aqueous media.