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. 2010 Feb 5;12(3):492-5.
doi: 10.1021/ol902660p.

Novel peptoid building blocks: synthesis of functionalized aromatic helix-inducing submonomers

Jiwon Seo  1 , Annelise E Barron, Ronald N Zuckermann
Affiliations

Novel peptoid building blocks: synthesis of functionalized aromatic helix-inducing submonomers

Jiwon Seo et al. Org Lett. .

Abstract

Peptoids, oligo-N-substituted glycines, can fold into well-defined helical secondary structures. The design and synthesis of new peptoid building blocks that are capable of both (a) inducing a helical secondary structure and (b) decorating the helices with chemical functionalities are reported. Peptoid heptamers containing carboxamide, carboxylic acid or thiol functionalities were synthesized, and the resulting peptoids were shown to form stable helices. A thiol-containing peptoid readily formed the homodisulfide, providing a convenient route to prepare peptoid helix homodimers.

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Figures

Figure 1
Figure 1
Peptoid submonomer design.
Figure 2
Figure 2
Synthesis of functionalized peptoid heptamers.
Figure 3
Figure 3
CD spectra of peptoids in acetonitrile (13, 14, 15, 16, and 19: 50 μM; 20 and 21: 46 μM) were recorded as per-residue molar ellipticity (deg cm2/dmol). Data were aquired at room temperature. (A) Comparison of amide functionalized peptoids 14 – 16 and control peptoid 13. (B) Comparison of amide peptoid 15 and acid peptoid 19. Also the effect of peptoid homodimerization via disulfide (20 and 21).
Scheme 1
Scheme 1
Synthesis of 6 (Nspe-thiol).
Scheme 2
Scheme 2
Synthesis of 11 (Nspe-acid) and 12 (Nspe-amide).
See this image and copyright information in PMC

References

    1. Branden C, Tooze J. Introduction to Protein Structure. 2nd. Garland Publishing Inc.; New York, NY: 1999.
    1. Barron AE, Zuckermann RN. Curr Opin Chem Biol. 1999;3:681–687. - PubMed
    1. Simons RJ, Kania RS, Zuckermann RN, Huebner VD, Jewell DA, Banville S, Ng S, Wang L, Rosenberg S, Marlowe CK, Spellmeyer DC, Tan R, Frankel AD, Santi DV, Cohen FE, Bartlett PA. Proc Natl Acad Sci USA. 1992;89:9367–9371. - PMC - PubMed
    2. Fowler SA, Blackwell HE. Org Biomol Chem. 2009;7:1508–1524. - PMC - PubMed
    1. Murphy JE, Uno T, Hamer JD, Cohen FE, Dwarki V, Zuckermann RN. Proc Natl Acad Sci USA. 1998;95:1517–1522. - PMC - PubMed
    1. Zuckermann RN, Kerr JM, Kent SBH, Moos WH. J Am Chem Soc. 1992;114:10646–10647.

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