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Synthesis

Chemical ligation reaction creates permanent thiol links

February 27, 2006 | A version of this story appeared in Volume 84, Issue 9

A chemical ligation process has been devised for permanently adding organic functional groups and compounds to cysteine and other thiols (J. Am. Chem. Soc. 2006, 128, 2544). The selenosulfide-based ligation and subsequent rearrangement with loss of the selenium (shown) was developed by David Crich and coworkers at the University of Illinois, Chicago. Benjamin G. Davis of the University of Oxford, who helped develop a similar but impermanent disulfide-based chemical ligation method, comments that separate selenosulfide-based ligations and rearrangements were known before but that Crich's technique "nicely combines them. As it stands, it will be a useful conjugation method for free thiols." If the reaction can be demonstrated to extend to protein-based thiols, as the paper suggests should be possible, it could be broadly useful for chemical protein ligation, Davis says. Crich and coworkers note that "applications in combinatorial chemistry and for the attachment of a wide variety of groups, including poly(ethylene glycol) and fluorous chains and oligosaccharide units to thiols of biological interest, are currently under development."

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