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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Abdelmoty, I., Albericio, F., Carpino, L.A. et al. Structural studies of reagents for peptide bond formation: Crystal and molecular structures of HBTU and HATU. Lett Pept Sci 1, 57–67 (1994). https://doi.org/10.1007/BF00126274
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DOI: https://doi.org/10.1007/BF00126274