Synthesis and Characterization of Retro-Inverso Peptides (VVRRVV and vvrrvv) and Their Derivatives towards Antimicrobial Applications

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dc.contributor.advisor Xu, Bing
dc.contributor.author Jiang, Yujie
dc.date.accessioned 2017-06-13T18:31:02Z
dc.date.available 2017-06-13T18:31:02Z
dc.date.issued 2017 en
dc.identifier.uri http://hdl.handle.net/10192/33992
dc.description.abstract This study investigates the antibacterial activities of hexapeptides and derivatives. The use of solid phase and liquid phase synthesis produces a pair of enantiomeric hexapeptides (VVRRVV and vvrrvv) and the relevant derivatives (Ac-vvrrvv and Ac-vvrrvv-C12) in moderate yields. VVRRVV and vvrrvv form heterogeneous aggregates in PBS buffer at pH 7.4 and show little toxicity on the mammalian cells tested. Both VVRRVV and vvrrvv inhibit 55% of E. coli growth at 16 h and 35% of growth at 24 h at the concentrations ranging from 20 μM to 100 μM. N-terminal acylation (e.g., Ac-VVRRVV and Ac-vvrrvv) results in decreased inhibition activities. C-terminal modification via addition of a long hydrocarbon chain leads to slight increase of the inhibition activity. The co-incubation with Ac-vvrrvv-C12 and vancomycin decreases the activity of vancomycin against E. coli. These results suggest that Ac-vvrrvv-C12 likely leads to cell death by embedding itself in the lipid bilayer, altering the composition and properties of the bacterial membrane, and disrupting homeostasis. It is also possible that Ac-vvrrvv-C12 forms aggregates around the outer membrane and prohibits ion exchange, an assumption that agrees with declined inhibition by vancomycin in the presence of Ac-vvrrvv-C12. en
dc.language.iso en en
dc.rights Copyright by Yujie Jiang 2017. en
dc.title Synthesis and Characterization of Retro-Inverso Peptides (VVRRVV and vvrrvv) and Their Derivatives towards Antimicrobial Applications en
dc.type Thesis
dc.contributor.department Department of Chemistry en


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