New Hydrogen-Bonded Materials : Catalysts for Peptide Synthesis

This work involves studies of hydrogen-bonded materials that serve as catalysts and/or additives for the solid-phase synthesis of peptides; we obtained large quantities of these materials from a collaborator at PerSeptive Biosystems, Dr. Steve Kates. This work may be viewed as an important "spin-off" from our studies of hydrogen-bonded cocrystals. The most surprising result has been the discovery that the most-used additives for solid-phase peptide synthesis, HATU and HBTU do not have the uronium salt structures 1,2 proposed in the literature for over two decades but rather ar guanidinium N-oxides 3,4 !

This result has created quite a stir among workers in solid-phase peptide synthesis. Note below the structures of the guanidinium cations for 3 and 4. Despite the fact that these two materials have quite different crystal structures, the molecular structures of the guanidinium N-oxide cations are virtually identical!

This material is based upon work supported by the National Science Foundation under Grant No. DMR-0089257. Any opinions, findings and conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of the National Science Foundation (NSF).


Send content and research comments to Bruce Foxman ( foxman1@brandeis.edu)

Bruce Foxman ( foxman1@brandeis.edu)