Structural studies of reagents for peptide bond formation: Crystal and molecular structures of HBTU and HATU |
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| Authors: | Iman Abdelmoty Fernando Albericio Louis A. Carpino Bruce M. Foxman Steven A. Kates |
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| Affiliation: | (1) Department of Chemistry, Brandeis University, 02254 Waltham, MA, U.S.A.;(2) Department of Organic Chemistry, University of Barcelona, E-08028 Barcelona, Spain;(3) Department of Chemistry, University of Massachusetts, 01003 Amherst, MA, U.S.A.;(4) Biosearch Corporation, 75A Wiggins Avenue, 01730 Bedford, MA, U.S.A. |
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| Abstract: | ![]()
Summary X-ray structure determinations of HBTU and HATU, well-known reagents for peptide bond formation, show that the solid-state structures of these compounds differ markedly from those commonly presented in the literature. The solid-state structures are isomers of the N,N,N',N'-tetramethyluronium salt formulation commonly written for HBTU and HATU. HBTU and HATU, obtained either directly from synthesis or from CH3CN solution, crystallize as the guanidinium N-oxide isomers. Both compounds crystallize in nearly identical conformations, despite marked differences in crystal packing. |
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| Keywords: | X-ray structure Guanidinium Coupling reagents |
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