Solid-phase synthesis and antibiotic activities of cyclodecapeptides on the scaffold of naturally occurring Laterocidin

Bioorganic & Medicinal Chemistry Letters
Chunlan XuXiaoya Shang

Abstract

The development of new antibacterial therapeutic agents capable of halting microbial resistance is a chief pursuit in clinical medicine. Laterocidin and its analogues were synthesized for the first time by solid-phase synthesis method via linking of the carboxyl group on side chain of Aspartate to Rink resin with the protection of side chain alpha-carboxyl group of Aspartate by Dmab as a temporary alpha-COOH protecting group for the on-resin cyclization. Different configuration of N- and C-terminal was benefit to peptide cyclization. Laterocidin analogue 3 (Asp(1)-->Asn(1), Phe(4)-->Tyr(4) and d-Tyr(6)-->d-Phe(6)) demonstrated potent and broad antimicrobial properties, especially exhibited activity against clinical Methicillin-resistant Staphylococcus aureus (L-MRSA) and the gram-negative extended-spectrum beta-lactamases-producing Escherichia coli (ESBLs E. coli) and L-E.coli. This finding has important significance to exploit new antibiotic medicine.

References

Jan 25, 2002·Nature·Michael Zasloff
Aug 9, 2002·Nature·Rahul M KohliMichael D Burkart
Oct 11, 2002·The New England Journal of Medicine·Michael Zasloff
Aug 26, 2004·Antimicrobial Agents and Chemotherapy·V FrecerJ L Ding
Jul 26, 2006·Pharmacotherapy·Warren E Rose, Michael J Rybak

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Citations

Mar 30, 2018·World Journal of Microbiology & Biotechnology·Xu Yang, Ahmed E Yousef
Jul 5, 2017·Clinical and Experimental Pharmacology & Physiology·Haibo XingDa Li

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