Solid-Phase Synthesis of N-Substituted Glycine Oligomers (α‑Peptoids) and Derivatives

doi:10.3390/molecules15085282

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Molecules 2010, 15(8), 5282-5335; doi:10.3390/molecules15085282

Review

Solid-Phase Synthesis of N-Substituted Glycine Oligomers (α‑Peptoids) and Derivatives

Adrian S. Culf^1,2,* and Rodney J. Ouellette¹

¹ Atlantic Cancer Research Institute, 35 Providence Street, Moncton, NB. EIC 8X3, Canada ² Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, NB. E4L 1G8, Canada

* Author to whom correspondence should be addressed.

Received: 4 June 2010; in revised form: 14 July 2010 / Accepted: 2 August 2010 / Published: 4 August 2010

(This article belongs to the Special Issue Solid Phase Synthesis)

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Abstract: Peptoids (N-substituted polyglycines and extended peptoids with variant backbone amino-acid monomer units) are oligomeric synthetic polymers that are becoming a valuable molecular tool in the biosciences. Of particular interest are their applications to the exploration of peptoid secondary structures and drug design. Major advantages of peptoids as research and pharmaceutical tools include the ease and economy of synthesis, highly variable backbone and side-chain chemistry possibilities. At the same time, peptoids have been demonstrated as highly active in biological systems while resistant to proteolytic decay. This review with 227 references considers the solid-phase synthetic aspects of peptoid preparation and utilization up to 2010 from the instigation, by R. N. Zuckermann et al., of peptoid chemistry in 1992.

Keywords: N-substituted polyglycine oligomer; peptoid; solid phase synthesis; synthetic methods

Supplementary Files

Supplementary File 1:
Table 1S. Homo α-peptoid oligomer synthetic parameters (XLS, 42 KB)

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Cite This Article

MDPI and ACS Style

Culf, A.S.; Ouellette, R.J. Solid-Phase Synthesis of N-Substituted Glycine Oligomers (α‑Peptoids) and Derivatives. Molecules 2010, 15, 5282-5335.

AMA Style

Culf AS, Ouellette RJ. Solid-Phase Synthesis of N-Substituted Glycine Oligomers (α‑Peptoids) and Derivatives. Molecules. 2010; 15(8):5282-5335.

Chicago/Turabian Style

Culf, Adrian S.; Ouellette, Rodney J. 2010. "Solid-Phase Synthesis of N-Substituted Glycine Oligomers (α‑Peptoids) and Derivatives." Molecules 15, no. 8: 5282-5335.

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