DOI: 10.1073/pnas.95.8.4309. NMR determination of the major solution conformation of a peptoid pentamer with chiral side chains

NMR determination of the major solution conformation of a peptoid pentamer with chiral side chains

10.1073/pnas.95.8.4309

Crossref journal-article

Proceedings of the National Academy of Sciences

Proceedings of the National Academy of Sciences (341)

Abstract

Polymers of N-substituted glycines (“peptoids”) containing chiral centers at the α position of their side chains can form stable structures in solution. We studied a prototypical peptoid, consisting of five para -substituted ( S )- N -(1-phenylethyl)glycine residues, by NMR spectroscopy. Multiple configurational isomers were observed, but because of extensive signal overlap, only the major isomer containing all cis -amide bonds was examined in detail. The NMR data for this molecule, in conjunction with previous CD spectroscopic results, indicate that the major species in methanol is a right-handed helix with cis -amide bonds. The periodicity of the helix is three residues per turn, with a pitch of ≈6 Å. This conformation is similar to that anticipated by computational studies of a chiral peptoid octamer. The helical repeat orients the amide bond chromophores in a manner consistent with the intensity of the CD signal exhibited by this molecule. Many other chiral polypeptoids have similar CD spectra, suggesting that a whole family of peptoids containing chiral side chains is capable of adopting this secondary structure motif. Taken together, our experimental and theoretical studies of the structural properties of chiral peptoids lay the groundwork for the rational design of more complex polypeptoid molecules, with a variety of applications, ranging from nanostructures to nonviral gene delivery systems.

Bibliography

Armand, P., Kirshenbaum, K., Goldsmith, R. A., Farr-Jones, S., Barron, A. E., Truong, K. T. V., Dill, K. A., Mierke, D. F., Cohen, F. E., Zuckermann, R. N., & Bradley, E. K. (1998). NMR determination of the major solution conformation of a peptoid pentamer with chiral side chains. Proceedings of the National Academy of Sciences, 95(8), 4309â4314.

Authors 11

Philippe Armand (first)
Kent Kirshenbaum (additional)
Richard A. Goldsmith (additional)
Shauna Farr-Jones (additional)
Annelise E. Barron (additional)
Kiet T. V. Truong (additional)
Ken A. Dill (additional)
Dale F. Mierke (additional)
Fred E. Cohen (additional)
Ronald N. Zuckermann (additional)
Erin K. Bradley (additional)

References 26 Referenced 282

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M Day, D Kneller, I D Kuntz NMR Pack (Univ. of California, San Francisco, 1993). / NMR Pack by Day M (1993)
T G Goddard, D G Kneller sparky 3: NMR Assignment and Integration Software (Univ. of California, San Francisco, 1977). / sparky 3: NMR Assignment and Integration Software by Goddard T G (1977)
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10.1021/ja9617193

Dates

Type	When
Created	23 years, 1 month ago (July 26, 2002, 10:40 a.m.)
Deposited	3 years, 4 months ago (April 13, 2022, 3:44 p.m.)
Indexed	1 month, 1 week ago (July 23, 2025, 9:01 a.m.)
Issued	27 years, 4 months ago (April 14, 1998)
Published	27 years, 4 months ago (April 14, 1998)
Published Online	27 years, 4 months ago (April 14, 1998)
Published Print	27 years, 4 months ago (April 14, 1998)

Funders 0

None

BibTeX

@article{Armand_1998, title={NMR determination of the major solution conformation of a peptoid pentamer with chiral side chains}, volume={95}, ISSN={1091-6490}, url={http://dx.doi.org/10.1073/pnas.95.8.4309}, DOI={10.1073/pnas.95.8.4309}, number={8}, journal={Proceedings of the National Academy of Sciences}, publisher={Proceedings of the National Academy of Sciences}, author={Armand, Philippe and Kirshenbaum, Kent and Goldsmith, Richard A. and Farr-Jones, Shauna and Barron, Annelise E. and Truong, Kiet T. V. and Dill, Ken A. and Mierke, Dale F. and Cohen, Fred E. and Zuckermann, Ronald N. and Bradley, Erin K.}, year={1998}, month=apr, pages={4309–4314} }

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