Traceless chemical ligations from O-acyl serine sites

Mirna El Khatib; Mohamed Elagawany; Farukh Jabeen; Ekaterina Todadze; Oleg Bol'shakov; Alexander Oliferenko; Levan Khelashvili; Said A. El-Feky; Abdullah Asiri; Alan R. Katritzky

doi:10.1039/C2OB07050B

Traceless chemical ligations from O-acyl serine sites†

Mirna El Khatib,^a Mohamed Elagawany,^abc Farukh Jabeen,^ad Ekaterina Todadze,^a Oleg Bol'shakov,^a Alexander Oliferenko,^a Levan Khelashvili,^a Said A. El-Feky,^b Abdullah Asiri^e and Alan R. Katritzky*^ae

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^a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
E-mail: katritzky@chem.ufl.edu

^b Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig-44519, Egypt

^c Department of Organic Chemistry, College of Pharmacy, Misr University for Science and Technology, Al-Motamayez District, 6th of October, P.O. Box: 77, Egypt

^d Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan

^e Department of Chemistry, King Abdulaziz University, Jeddah, Saudi Arabia

Abstract

Chemical ligation via O- to N-acyl transfer of O-acylated serine containing peptides affords serine containing native peptides via 8- and 11-membered cyclic transition states opening the door to a wide variety of potential applications to peptide elaboration. The feasibility of these traceless chemical ligations is feasible as supported by computation.

Organic & Biomolecular Chemistry

Traceless chemical ligations from O-acyl serine sites†

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