Solid-phase synthesis and in vitro biological activity of a Thr4→Ser4 analog of daptomycin

Bioorganic and Medicinal Chemistry Letters

Volumn 25, Issue 23, 2015, Pages 5490-5494

  Lohani, Chuda Raj ^a   Taylor, Robert ^a   Palmer, Michael ^a   Taylor, Scott D ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

Antibiotics; Cyclic peptide; Daptomycin; Peptide synthesis

Indexed keywords

AMINO ACID DERIVATIVE; CALCIUM; DAPTOMYCIN; DAPTOMYCIN DERIVATIVE; GLUTAMIC ACID; KYNURENIC ACID; SERINE; THREONINE; TRYPTOPHAN; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT;

AMINO ACID SUBSTITUTION; ARTICLE; BIOLOGICAL ACTIVITY; CALCIUM BINDING; CHEMICAL BOND; CYCLIZATION; DRUG STRUCTURE; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; SOLID PHASE SYNTHESIS; ANALOGS AND DERIVATIVES; BACILLACEAE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; METABOLISM; MICROBIAL SENSITIVITY TEST; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BACILLACEAE; CALCIUM; DAPTOMYCIN; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; SERINE; SOLID-PHASE SYNTHESIS TECHNIQUES; THREONINE;

EID: 84946750351     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2015.10.072     Document Type: Article

References (19)

1. For recent reviews see: (a) N. Bionda, J.P. Pitteloud, and P. Cudic Future Med. Chem. 5 2013 1311
2. L. Robbel, and M.A. Marahiel J. Biol. Chem. 285 2010 27501
3. R.H. Baltz Curr. Opin. Chem. Biol. 13 2009 144
4. R.D. Arbeit, D. Maki, F.P. Tally, E. Campanaro, and B.I. Eisenstein Clin. Infect. Dis. 38 2004 1673
5. V.G. Fowler, H.W. Boucher, G.R. Corey, E. Abrutyn, A.W. Karchmer, M.E. Rupp, D.P. Levine, H.F. Chambers, F.P. Tally, G.A. Vigliani, C.H. Cabell, A.S. Link, I. DeMeyer, S.G. Filler, M. Zervos, P. Cook, J. Parsonnet, J.M. Bernstein, C.S. Price, G.N. Forrest, Fätkenheuer, G.M. Gareca, S.J. Rehm, H.R. Brodt, A. Tice, and S.E. Cosgrove N. Eng. J. Med. 355 2006 653
6. For recent reviews on cyclic lipodepsipeptides see: (a) N. Bionda, and P. Cudic Croat. Chem. Acta 84 2011 315
7. I.W. Hamley Chem. Commun. 2015 8574
8. J.A. Silverman, N.G. Perlmutter, and H.M. Shapiro Antimicrob. Agents Chemother. 47 2003 2538
9. T. Zhang, J.K. Muraih, N. Tishbi, J. Herskowitz, R.L. Victor, J. Silverman, S. Uwumarenogie, S.D. Taylor, M. Palmer, and E. Mintzer J. Biol. Chem. 289 2014 11584
10. A.S. Bayer, T. Schneider, and H.-G. Sahl Ann. N.Y. Acad. Sci. 1277 2013 139
11. J.A. Silverman, L.I. Mortin, A.D.G. VanPraagh, T. Li, and J. Alder J. Infect. Dis. 191 2005 2149
12. C.R. Lohani, R. Taylor, M. Palmer, and S.D. Taylor Org. Lett. 17 2015 748
13. Lam et al. also reported difficulties in forming the ester bond in the solid phase. See: H.Y. Lam, Y. Zhang, H. Liu, J. Xu, C.T.T. Wong, C. Xu, and X. Li J. Am. Chem. Soc. 135 2013 6272
14. Although the synthesis of Dap-DAPA4-E12 and Dap-DAPA4-E12-W13 were not performed entirely in the solid-phase, the amide linkage between DAPA4 and W13 or Kyn13 was readily accomplished in the solid-phase. See: P. Hart, L.H.J. Kleijn, G. de Bruin, S.F. Oppedijk, J. Kemminka, and N.I. Martin Org. Biomol. Chem. 12 2014 913
15. A.M. Ali, and S.D. Taylor Angew. Chem., Int. Ed. Engl. 48 2009 2024
16. Angew. Chem. 121 2009 2058
17. F. Albericio, M. Cases, J. Alsina, S.A. Triolo, L.A. Carpino, and S.A. Kates Tetrahedron Lett. 38 1997 4853
18. R. Krishnamoorthy, L.D. Vazquez-Serrano, J.A. Turk, J.A. Kowalski, A.G. Benson, N.T. Breaux, and M.A. Lipton J. Am. Chem. Soc. 128 2006 15392
19. J. Grunewald, S.A. Sieber, C. Mahlert, U. Linne, and M.A. Marahiel J. Am. Chem. Soc. 126 2004 17025