Synthesis and characterization of diamino analog of dithiothreitol

ORGN 652

Nicole M. McElfresh, Department of Biochemistry, University of Wisconsin at Madison, 433 Babcock Drive, Madison, WI 53706-1544 and Ronald T. Raines, raines@biochem.wisc.edu, Departments of Chemistry and Biochemistry, University of Wisconsin-Madison, 433 Babcock Drive, Madison, WI 53706.
Dithiothreitol (Cleland's reagent, DTT) is used extensively for the reduction of disulfide bonds. DTT is a very strong reducing agent, but is slow to act at pH 7 due to the low acidity of its thiol groups (pK1 = 9.2). Several synthetic reducing agents are known to act faster than DTT, but none have been able to match its reduction potential. The diamino analog of DTT, in which the two hydroxyl groups are replaced with amino groups, was designed to increase the rate of its reaction without affecting its reduction potential. The synthesis of this DTT analog will be presented, along with a comparison of its reduction potential and rate of reaction to authentic DTT.
 

Asymmetric Reactions, Combinatorial Chemistry, Molecular Recognition and Self-Assembly, Proteins, Peptides, Amino Acids and Enzyme Inhibitors
8:00 PM-10:00 PM, Wednesday, March 28, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007