Stereochemical characterization of cyclotides from Cerrado species using Raman optical activity

• Grant number: 14/50304-9
• Support Opportunities: Regular Research Grants
• Start date: March 01, 2015
• End date: February 28, 2017
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Agreement: University of Manchester
• Principal Investigator: Vanderlan da Silva Bolzani
• Grantee: Vanderlan da Silva Bolzani
• Principal researcher abroad: Ewan William Blanch
• Institution abroad: University of Manchester, England
• Host Institution: Instituto de Química (IQ). Universidade Estadual Paulista (UNESP). Campus de Araraquara. Araraquara , SP, Brazil
• Associated research grant: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery, AP.CEPID

Abstract

This application is based on an ongoing scientific collaboration formalized in December 2012 between Prof. Vanderlan Bolzani (UNESP) and Dr. Ewan Blanch (University of Manchester). This collaboration was establised by two FAPESP-sponsored one-year post-doctoral fellowships awarded to Drs João M. Batista Jr and Andrea N. L. Batista from NuBBE group in Brazil (grant numbers BEPE 2012/13739-1 and BEPE 2012/16484-4, respectively). Their projects aimed to develop conformational and configurational Raman optical activity (ROA) studies on proteins and natural products at the University of Manchester, an approach not used by any other Brazilian natural product group. Over the past 15 years the group called NuBBE coordinated by Prof. Bolzani has been devoted to studying different aspects of secondary metabolites from the Brazilian biodiversity. More recently, this group has been focused on the study of plant cyclic peptides and circular proteins called cyclotides. These compounds, especially the latter, are highly biologically active and very interesting from a structural and biosynthetic point of view. However, their full strucutural characterization including secondary structure and chirality may be very challenging. From our previous collaborative results, ROA has proven to be a very powerful technique to study solution-state conformation of cyclic peptides and proteins resulting in one paper published in PhyChemChemPhys (PCCP 2013,15,20147) and two submitted to Chirality and Phytochemistry journals. This project consolidates the above-mentioned international collaboration and is an important step forward to generate novel ROA spectral libraries for cyclotides and other plant proteins, which have never been investigated using vibrational optical activity before. (AU)

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

BATISTA, JR., JOAO M.; BLANCH, EWAN W.; BOLZANI, VANDERLAN DA SILVA. Recent advances in the use of vibrational chiroptical spectroscopic methods for stereochemical characterization of natural products. NATURAL PRODUCT REPORTS, v. 32, n. 9, p. 1280-1302, 2015. (11/22339-4, 13/07600-3, 14/25222-9, 14/50304-9)

MONTEIRO, AFIF F.; BATISTA, JR., JOAO M.; MACHADO, MICHELLE A.; SEVERINO, RICHELE P.; BLANCH, EWAN W.; BOLZANI, VANDERLAN S.; VIEIRA, PAULO C.; SEVERINO, VANESSA G. P.. Structure and Absolute Configuration of Diterpenoids from Hymenaea stigonocarpa. Journal of Natural Products, v. 78, n. 6, p. 1451-1455, JUN 2015. (13/07600-3, 14/50304-9)

BERNARDINO, K.; PINTO, M. E. F.; BOLZANI, V. S.; DE MOURA, A. F.; BATISTA JUNIOR, J. M.. Pinpointing disulfide connectivities in cysteine-rich proteins. CHEMICAL COMMUNICATIONS, v. 53, n. 53, p. 7337-7340, JUL 7 2017. (15/07089-2, 13/07600-3, 14/25222-9, 14/50304-9, 13/07296-2, 12/15147-4)