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Cited by 953

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Peptoids: a modular approach to drug discovery.

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Simon, R J, Kania, R S, Zuckermann, R N, Huebner, V D, Jewell, D A, Banville, S, Ng, S, Wang, L, Rosenberg, S, Marlowe, C K·1992·Proceedings of the National Academy of Sciences

Abstract

Peptoids, oligomers of N-substituted glycines, are described as a motif for the generation of chemically diverse libraries of novel molecules. Ramachandran-type plots were calculated and indicate a greater diversity of conformational states available for peptoids than for peptides. The monomers incorporate t-butyl-based side-chain and 9-fluorenylmethoxy-carbonyl alpha-amine protection. The controlled oligomerization of the peptoid monomers was performed manually and robotically with in situ activation by either benzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate or bromotris(pyrrolidino)phosphonium hexaflurophosphate. Other steps were identical to peptide synthesis using alpha-(9-fluorenylmethoxycarbonyl)amino acids. A total of 15 monomers and 10 oligomers (peptoids) are described. Preliminary data are presented on the stability of a representative oligopeptoid to enzymatic hydrolysis. Peptoid versions of peptide ligands of three biological systems (bovine pancreatic alpha-amylase, hepatitis A virus 3C proteinase, and human immunodeficiency virus transactivator-responsive element RNA) were found with affinities comparable to those of the corresponding peptides. The potential use of libraries of these compounds in receptor- or enzyme-based assays is discussed.

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Metadata

Authors
Simon, R. J., Kania, R. S., Zuckermann, R. N., Huebner, V. D., Jewell, D. A., Banville, S., Ng, S., Wang, L., Rosenberg, S., & Marlowe, C. K.
Venue
Proceedings of the National Academy of Sciences
Published
1992-10-15
Volume
89
Issue
20
Pages
9367-9371
ISSN
  • 0027-8424 (ISSN-L)
  • 1091-6490
OpenAlex
W2142759234
Cited by
953
References
0
FWCI
8.40
Type
journal article
Language
en
Open access
green

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CoChat. (2026). Citation check: Peptoids: a modular approach to drug discovery. https://app.cochat.ai/papers/10.1073/pnas.89.20.9367
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Simon, R. J., Kania, R. S., Zuckermann, R. N., Huebner, V. D., Jewell, D. A., Banville, S., Ng, S., Wang, L., Rosenberg, S., & Marlowe, C. K. (1992). Peptoids: a modular approach to drug discovery. Proceedings of the National Academy of Sciences. https://doi.org/10.1073/pnas.89.20.9367

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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).

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