S. S. Panda, A. A. Oliferenko, H. M. Marwani, A. R. Katritzky, “Effects of preorganization and hydrogen bonding on intramolecular chemical ligation of (N)-and (O)-acyl isopeptides”, Mendeleev Commun., 2014, Volume 24, Issue 2,Pages 75

This article is cited in 4 papers

Communications

Effects of preorganization and hydrogen bonding on intramolecular chemical ligation of (N)-and (O)-acyl isopeptides

S. S. Panda^a, A. A. Oliferenko^a, H. M. Marwani^b, A. R. Katritzky^ab

^a Department of Chemistry, University of Florida, Gainesville, USA
^b Chemistry Department, King Abdulaziz University, Jeddah, Saudi Arabia

Abstract: The ease of intramolecular N-to N-and O-to N-acyl transfers in (N)-acyl isopeptides and (O)-acyl isopeptides was found to be governed by preorganization rationalized in terms of geometrical and energetic characteristics of the linear isopeptide backbone, which depends on the chain length. Intramolecular hydrogen bonding was found another important factor of reactivity able to stabilize the chemical ligation transition state.

Language: English

DOI: 10.1016/j.mencom.2014.03.002