The Mitsunobu reaction: A novel method for the synthesis of bifunctional maleimide linkers

✍ Scribed by Michael A. Walker

• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 276 KB
• Volume: 35
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)75785-6

✦ Synopsis

Compounds l-7 were synthesized from maleimicfe and the corresponding alcohols using a novel application of the Mitsunobu reaction. This procedure allows the direct formation of a variety of bifunctional linker compounds. Bifunctional linkers, with a maleimido group attached to one end and a connectable functionality (eg. -OH, -NH2, -COzH) on the opposite end, are useful for modifying proteins and peptides. 1 The maleimido group is one of a number of functionalities that are reactive with thiol nucleophiles.2 thus allowing coupling of the linker to cysteine or -SH containing molecules (cf. scheme). The other molecule can be attached to the opposite end (2) by means of an amide, ester, ether or other type of bond. These linkers are useful for synthesizing: peptide-conjugate haptens, immobilized antibodies or enzymes4, antibody-antibody conjugates5, immuno-conjugates or -toxins,6 enzyme inhibitors and enzyme probes.7