Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 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.

PubMed Disclaimer

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

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

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.

Publication types