SYNTHESIS OF FUNCTIONALIZED MACROCYCLIC PEPTIDES
-
1
Auburn University, United States
Macrocyclic peptides have been extensively used as chemical tools or probes for the understanding and interrogating of biological systems. These macrocyclic peptides are known to have high receptor binding activity, cell permeability, lower toxicity, specificity and metabolic stability due to enhanced resistance to proteolytic degradation as opposed to linear peptides. There are two conventional methods for macrocyclization of peptides. The first produces head to tail cyclic peptides in which a ring is formed by amide bond formation between the N-terminal amine and the C-terminal carboxylic acid while the other is side-chain-to-side-chain cyclisation. There are scanty reports of the incorporation of fluorescent probes which could help in visualization of the interactions mediated by these macrocyclic peptides. It is known that macrocyclic peptides have the capacity for functional fine-tuning. Based on this unique property of macrocyclic peptides, we report a general method for the synthesis of functionalized macrocyclic peptides. Our method is chemo-selective and site-selective in nature. Such functionalized macrocyclic peptides would be important for protein-protein interaction (PPI), post translational modification and cell-imaging studies.
References
Cardote, T. A. F. and Ciulli, A. Chem. Med. Chem. 2016, 11, 787-794
Giordanetto, F. and Kihlberg, J. J. Med. Chem. 2014, 57 (2), 278-295
White, C. J. and Yudin, A. K. Nat. Chem, 2011, 2, 509-523
Keywords:
Macrocyclic Peptides,
protein-protein interaction (PPI),
post translation modification,
Flourescent probe,
Cell-imaging
Conference:
National Organization for the Professional Advancement of Black Chemists and Chemical Engineers (NOBCChE) 45th Annual Conference , Orlando, Florida, United States, 17 Sep - 20 Sep, 2018.
Presentation Type:
Oral Presentation
Topic:
Biochemistry
Citation:
Nwajiobi
O and
Raj
M
(2019). SYNTHESIS OF FUNCTIONALIZED MACROCYCLIC PEPTIDES.
Front. Chem.
Conference Abstract:
National Organization for the Professional Advancement of Black Chemists and Chemical Engineers (NOBCChE) 45th Annual Conference .
doi: 10.3389/conf.fchem.2018.01.00051
Copyright:
The abstracts in this collection have not been subject to any Frontiers peer review or checks, and are not endorsed by Frontiers.
They are made available through the Frontiers publishing platform as a service to conference organizers and presenters.
The copyright in the individual abstracts is owned by the author of each abstract or his/her employer unless otherwise stated.
Each abstract, as well as the collection of abstracts, are published under a Creative Commons CC-BY 4.0 (attribution) licence (https://creativecommons.org/licenses/by/4.0/) and may thus be reproduced, translated, adapted and be the subject of derivative works provided the authors and Frontiers are attributed.
For Frontiers’ terms and conditions please see https://www.frontiersin.org/legal/terms-and-conditions.
Received:
19 Oct 2018;
Published Online:
17 Jan 2019.
*
Correspondence:
Dr. Monika Raj, Auburn University, Auburn, United States, mzr0068@auburn.edu