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. 2012 Dec 21;14(24):6162-5.
doi: 10.1021/ol302850n. Epub 2012 Dec 4.

Substituted imidazo[1,2-a]pyridines as β-strand peptidomimetics

Chang Won Kang  1 , Yongmao Sun, Juan R Del Valle
Affiliations

Substituted imidazo[1,2-a]pyridines as β-strand peptidomimetics

Chang Won Kang et al. Org Lett. .

Abstract

New conformationally extended dipeptide surrogates based on an imidazo[1,2-a]pyridine scaffold are described. Efficient synthesis and incorporation into host peptides affords structures with native side-chain functionality and hydrogen bonding elements on one face of the backbone. Structural analysis by NMR suggests that model peptidomimetics adopt a β-strand-like conformation in solution.

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Figures

Figure 1
Figure 1
Design of IP-based β-strand mimics.
Figure 2
Figure 2
ROESY spectrum of 8 (500 MHz in CDCl3) highlighting key Overhauser correlations.
Figure 3
Figure 3
Structures of possible turn conformations of 8.
Scheme 1
Scheme 1
Synthesis of orthogonally-protected IP-based extended dipeptide surrogates.
Scheme 2
Scheme 2
Synthesis and selected ROESY correlations (in red) of tetrapeptide mimic 6.
Scheme 3
Scheme 3
Synthesis of heptapeptide mimic 8 and conformational analysis by 1H NMR.
See this image and copyright information in PMC

References

    1. Dou Y, Baisnée P-F, Pollastri G, Pécout Y, Nowick J, Baldi P. Bioinformatics. 2004;20:2767. - PubMed
    2. Somers WS, Phillips SEV. Nature. 1992;359:387. - PubMed
    3. Puglisi JD, Chen L, Blanchard S, Frankel AD. Science. 1995;270:1200. - PubMed
    4. Derrick JP, Wigley DB. Nature. 1992;359:752. - PubMed
    5. Colon W, Kelly JW. Biochemistry. 1992;31:8654. - PubMed
    1. Yang J, Cron P, Good VM, Thompson V, Hemmings BA, Barford D. Nat. Struct. Mol. Biol. 2002;9:940. - PubMed
    1. Nassar N, Horn G, Herrmann C, Block C, Janknecht R, Wittinghofer A. Nat. Struct. Biol. 1996;3:723. - PubMed
    1. Strickland CL, Windsor WT, Syto R, Wang L, Bond R, Wu Z, Schwartz J, Le HV, Beese LS, Weber PC. Biochemistry. 1998;37:16601. - PubMed
    2. Long SB, Casey PJ, Beese LS. Structure. 2000;8:209. - PubMed
    1. Tyndall JDA, Fairlie DP. J. Mol. Recog. 1999;12:363. - PubMed
    2. Fairlie DP, Tyndall JDA, Reid RC, Wong AK, Abbenante G, Scanlon MJ, March DR, Bergman DA, Chai CLL, Burkett BA. J. Med. Chem. 2000;43:1271. - PubMed

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