Novel water-soluble aminophosphinothiol for traceless Staudinger ligation

ORGN 477

Annie Tam1, Matthew B. Soellner1, and Ronald T Raines, raines@biochem.wisc.edu2. (1) Department of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, WI 53706, (2) Departments of Biochemistry and Chemistry, University of Wisonsin-Madison, 433 Babcock Drive, Madison, WI 53706
The Staudinger ligation is recognized as an effective strategy for the synthesis of amide bonds between a C-terminal thioester and an N-terminal azide in a peptide. Existing reagents for manifesting a traceless Staudinger ligation are not soluble in aqueous environments. Due to the organic solvent incompatibility of most polypeptides and proteins, we aim to extend the scope of the Staudinger ligation to water. Here, we report a novel class of water-soluble phosphinothiols that exploit the use of charge to effect traceless Staudinger ligation in moderate yields in an all-aqueous environment.

 

New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006