The synthesis and biological testing of bacilysin analogues | Zendy

Keith Robertson | Zendy; Cormac D. Murphy | Zendy; Francesca Paradisi | Zendy

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The synthesis and biological testing of bacilysin analogues

Author(s) -

Keith Robertson,

Cormac D. Murphy,

Francesca Paradisi

Publication year - 2013

Publication title -

amino acids

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.894

H-Index - 118

eISSN - 1438-2199

pISSN - 0939-4451

DOI - 10.1007/s00726-013-1571-4

Subject(s) - ketone , chemistry , yield (engineering) , ether , selectivity , dipeptide , iodide , antibacterial activity , scaffold , diketopiperazines , organic chemistry , coupling reaction , combinatorial chemistry , bacteria , catalysis , peptide , biochemistry , materials science , biology , medicine , biomedical engineering , metallurgy , genetics

A series of compounds based on the structure of bacilysin were synthesised and tested for antibacterial activity. The key steps in the syntheses are the coupling of an iodide to a diketopiperazine (DKP) and mono-lactim ether scaffold, respectively. The diastereoselectivity of the coupling reactions was dependant on the scaffold, with selectivity for DKP of about 4:1 and mono-lactim ether exceeding 98:2. Subsequent elaboration of the compounds to give open chain dipeptides and DKPs that mimic the structure of bacilysin but substitute the epoxy ketone for a saturated or unsaturated ketone is described. Overall yield from coupling to final product was between 5 and 21 %, with the yield of the saturated products notably higher. The open chain dipeptides demonstrated moderate antibacterial and antifungal activity.

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