Professor Felix M. Rivas Rivera synthesized antibacterial peptides called cicadapeptins. Cicadapeptins are isolated from a fungus that infects cicadas and have a unique amino acid composition. They have demonstrated antibacterial activity against Bacillus cereus, B. subtilis, and Escherichia coli. Rivas synthesized fragments of cicadapeptin using solid phase peptide synthesis and plans to couple the fragments together to fully synthesize cicadapeptins I and II to further study their antibacterial properties. A career in research and academia is possible through education and with help from mentors.

1. Antibacterial Agents: Synthesis of Cicadapeptins
Professor Felix M. Rivas Rivera
November 6, 2014
CayeyP.R.

2. My StoryGraduated from UPR‐Cayeyin 1996How did I get here?

3. Education
High School: Maestro Ladi, Vega Alta, Puerto Rico
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Participated in Science Competitions
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Took Extra Science and Math Courses
Bachelor of Science in Chemistry: Universidad de Puerto Rico –Cayey
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Participated in Undergraduate Research
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Honors College
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Undergraduate Thesis
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President of Chemistry Club

4. Education (continued)
Doctor of Philosophy in Chemistry: University of Buffalo –SUNY
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Synthesis of Organic Molecules for use as Catalysts
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Ford Foundation Pre‐Doctoral Fellowship
Post‐Doctoral Studies in Medicinal Chemistry: University of Wisconsin –Milwaukee
Synthesis of Organic Molecules for use as Anti‐Seizure AgentsNN

5. Real World (Education Continued!)
Instructor of Organic Chemistry –Chicago State University 2006
Assistant Professor of Chemistry –Chicago State University 2006
Assistant Professor of Chemistry Tenured–Chicago State University 2012
Associate Professor of Chemistry –Chicago State University 2013
Department of Chemistry, Physics and Engineering Studies

6. Research Interests
OClAnthocyanin(flavyliumion) OHHORR'
Synthesis of Dyes for
Dye Sensitized Solar Cells
Synthesis of Antibacterial Agents
NHHNNHHNNHHN NNONH2OOOOOOOR1R2HOHONH2O1:R1=CH3,R2=HCicadapeptinI2:R1=H,R2=CH3CicadapeptinII
Synthesis of New Ligandsfor Organometallic
Chemistry Catalyzed Organic Reactions

7. Example of Antibacterial Agents
quinolone
tetracycline
penicillin
Erythromycin

8. Antibacterial Agents: Synthesis of Cicadapeptins
Abstract
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Cicadapeptinsare short sequences of seven amino acidsisolated from the EntomopathogenicFungusCordycepsheteropoda.Among the unique amino acidspresent in Cicadapeptins are two aminoisobutyricacids and two hydroxyprolineamino acids.Preliminary studies showed that Cicadapeptins act as good antibacterial agentsagainstBacillus cereus,B. subtilis, andEscherichia coli.In agar disk/diffusion assays using 100 mg/disk, Cicadapeptins I and II produced clear kill zones againstBacillus cereus(12‐13 mm),B. subtilis(11‐13 mm), and Escherichia coli(16 mm).To further explore their antibacterial properties their synthesis was startedusing solid‐supported organic synthesis. A polystyrene‐based resin with 2‐chlorotrityl chloride as linker was used. Two fragments of three amino acids each were synthesized. The synthetic approach, experimental procedure and results will be presented.

9. Take home messages
Synthesis of antibacterial peptide with unique amino acids
A career as a researcher
and/or professoris possible for

10. Cicadapeptins from Fungus that infects Cicadas

11. Cicadapeptins
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isolated from fungus on Cicadas
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short peptide
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α‐Helical structure
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unique amino acids
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antibacterial properties
310‐helix side view
310‐helix top view

12. Building!

13. Synthesis of Cicadapeptins
NHHNNHHNNHHN NNONH2OOOOOOOR1R2HOHONH2OH2NHN NH H2NNH HN NNONH2OOOOOOOR1R2HOHONH2OOHOHFragmentAFragmentBFragmentC

14. Peptide Bond Formation
HN OHFmocOH2NORO+ HN OROHN FmocONewBondMade+H2O
HOMEWORK
How does this reaction occur?
How does your body performs this reaction a million times?

15. Synthesis of Fragment A
HN OOH NH OOH HNOHDIPEA, CH2Cl2 HNNHHN OOFragmentA14HOBt,DIC,DMFFmocFmocHOBt,DIC,DMFFmocOresinFmocO HN OFmocOpiperidineH2NOOHN OONH OFmocpiperidineHN OOH2NOO

16. Synthesis of Fragment B
NH OOHi) iii) 4,HOBt,DICDMF5Fmoc NHHNNH OOOO HN OFmocC(Ph)3ii)Piperidine(50%) NH OHO HNOH2NOO HN O2C(Ph)3FmocC(Ph)3DIPEA, CH2Cl2iiiPiperidine(50%) resinFragmentB

17. Experimental Procedure
Solid Phase Synthesis
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Solid Support
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Solvents
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Amino Acids
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Coupling Reagents
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Glassware
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Reaction Monitoring
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Purification Techniques
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Instrumentation for Characterization

18. Future Work
H2N HNNHHNNHHNNH OOOOOR1R2NH2OFragmentANNOOOFragmentBi)HOBt,DIC,DMF+NH HN NH OHOOONH2OFragmentA'' (WesternHemisphere) FmocHN NH HN OOR1R2FragmentA' (EasternHemisphere) FmocNH i)HOBt,DIC,DMFii)Piperidine(50%) OHOOii)removalfromsolidsupportandremovalofprotectinggroups(PG) PGPG
CicadapeptinsI and II

19. Summary and take home messages
Synthesis of antibacterial peptide with unique amino acids
A career as a researcher
and/or professoris possible for

20. Acknowledgements
Department of Chemistry
Physics and Engineering Studies
Undergraduate Students
ZandraFloyd
George Howell

21. Alumni from Rivas Lab
ValentinTorresB.S. Biology; Teacher at Chicago Public Schools
ZandraFloydB.S. Chemistry; MS‐Chemistry IIT; Nuclear Chemist
George HowellB.S. Chemistry; Working for Cargill
Samuel NtrakwaB.S. Chemistry; MS‐Public Health Australia
Laurence QuinnB.S. Chemistry; Chemist, Applying to Graduate Schools
Charity BurgosB.S. Chemistry, Graduate student at Atlanta University
Chirag ThakarB.S. Biology; Pharm. D. Ohio State Univ., Pharmacist at Ohio, US
Kiel WashH.S. Morgan Academy High School, Engineering Major IIT
Rachel HawkinsB.S. Chemistry; Working for Cargill
Isabel AnayaB.S. Biology; Chicago State University, Senior Class 2015
Horace JamesB.S. Chemistry; Chicago State University, Senior Class 2014
Valencia KeysB.S. Psychology; Chicago State University, Senior Class 2015
BriticeGoinsPre‐Pharm.; Pharmacy School at Chicago State University
Veronica SmartB.S. Chemistry; Chicago State University, Senior Class 2016
Patrick AdampteyB.S. Chemistry; Chicago State University, Senior Class 2016
Alan ToledoB.S. Chemistry; Chicago State University, Senior Class 2015
Ylse BenitezB.S. Biology; Chicago State University, Senior Class 2016

22. Other Students
Bonnie GumkoskiM.S.; University of Illinois Dietetics Program
Agnes KisaiApplying to Medical School
SitatianRushM.S.; Rush University, Chicago
Pablo GuzmanPh.D.; Emory University
Tameka BarlettSummer Pre‐Dentistry Program
Tabatha WilliamsMedical School Wisconsin Madison
Luis RiveraMedical School
Ruth OsborneUniversity of Illinois at Chicago PREP
Katie StanislowskiPharmacy School Chicago State University

23. How to get whereI am now? Answer: A Lot of People Helped Me!

24. At Cayeythe Academic Side
Dr. Robert Ross
Ms. Rosita Baez
Dr. MirthaTrujillo
Dr. Luz E. Torres
Dr. WilfredoResto
Dr. MercedesRivera
Dr. GenaroOrtiz
Dr. JairoPardo
Dr. Juan Estevez
Dr. Edgar Llera
Dr. Nestor Carballeira(UPR‐RP)
Dr. Alba Reyes (Graduate Student)
Dr. Mayra Pagan (Graduate Student)
Dr. Carmen Umpierre
All other Professors in the Sciences
UPR‐CayeyHonors Program
Dr. Angel Lopez (student)
How to get whereI am now? Answer: A Lot of People Helped Me!
At Cayeythe Non‐Academic Side
MBRS Office Staff
Dr. GlamarieBurgos (student)
Students from Chemistry Club
Students and faculty from BBB
UPR‐CayeyHonors Program Staff

25. At SUNY Buffalo:
Dr. Luis A Colon
Dr. Steven T. Diver
Dr. John Richard
Ford Foundation Pre‐Doctoral
Dr. GlamarieBurgos (student)
Students at Steven T. Diver Lab
At University of Wisconsin:
Dr. James Cook
Dr. Luis A. Colon
Dr. GlamarieBurgos
Students at James Cook Lab
At Chicago State University:
Dr. LeRoyJonesDr. Mel Sabella
Dr. Luis A. ColonDr. Mike Mimnaugh
Dr. David KanisDr. Mark E. Duban
Dr. GlamarieBurgos Mr. IsmaelReyna
Mr. Fernando DiazMs. Leticia Carillo
Dr. Pablo Guzman Ford Foundation Senior Fellows
I still need HELP!

26. It is OK to ask and accept HELP,
you will need it!
Take Home MessagePart II

27. Questions!
Felix M. Rivas
Email: frivas@csu.edu
Text: 773‐977‐5012

28. Chicago