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Molecules 2010, 15(7), 4961-4983; doi:10.3390/molecules15074961
Article

Solid-Phase Synthetic Route to Multiple Derivatives of a Fundamental Peptide Unit

1,* , 1, 2, 2 and 1,*
1 Department of Chemistry and Chemical Biology, Indiana University-Purdue University, Indianapolis, 402 N. Blackford Street, Indianapolis, IN 46202, USA 2 Department of Medicinal Chemistry, Jagiellonian University Medical College, 9 Medyczna Street, 30-688 Kraków, Poland
* Authors to whom correspondence should be addressed.
Received: 7 June 2010 / Revised: 23 June 2010 / Accepted: 12 July 2010 / Published: 20 July 2010
(This article belongs to the Special Issue Solid Phase Synthesis)
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Abstract

Amino acids are Nature’s combinatorial building blocks. When substituted on both the amino and carboxyl sides they become the basic scaffold present in all peptides and proteins. We report a solid-phase synthetic route to large combinatorial variations of this fundamental scaffold, extending the variety of substituted biomimetic molecules available to successfully implement the Distributed Drug Discovery (D3) project. In a single solid-phase sequence, compatible with basic amine substituents, three-point variation is performed at the amino acid a-carbon and the amino and carboxyl functionalities.
Keywords: Distributed Drug Discovery (D3); fundamental peptide scaffold; biomimetics; solid-phase organic synthesis; combinatorial chemistry Distributed Drug Discovery (D3); fundamental peptide scaffold; biomimetics; solid-phase organic synthesis; combinatorial chemistry
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Scott, W.L.; Zhou, Z.; Zajdel, P.; Pawłowski, M.; O’Donnell, M.J. Solid-Phase Synthetic Route to Multiple Derivatives of a Fundamental Peptide Unit. Molecules 2010, 15, 4961-4983.

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