Nicholas M. Leonard, Jarmila Bruncková
Jan 1, 2012
Citations
0
Influential Citations
3
Citations
Journal
Organic Preparations and Procedures International
Abstract
Succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate (2, SMCC) has found utility in numerous areas of chemistry and biotechnology. The well-established chemoselective reactivity of SMCC has promoted its use as a heterobifunctional linker in immumoassays,1 radio-labeling for tumor imaging,2–4 therapeutic agent delivery,5,6 the immobilization of oligonucleotides on glass surfaces,7 and more recently, in boron neutron capture therapy.8 The high demand for SMCC has resulted in numerous methods for its preparation, although to date, a concise, high-yielding synthesis has not been reported. SMCC was first synthesized by Yoshitake and co-workers in a three-step process that hinged on an acetic acid/sodium acetate promoted cyclization, and provided the desired product in 21% overall yield from trans-4-(aminomethyl)cyclohexane carboxylic acid (1).9 In 1991, Nielsen and Buchardt reported the formation of SMCC through the one-pot, DCC promoted esterification/cyclization of trans-4-(aminomethyl)cyclohexane carboxylic acid (1) in 75% yield.10