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Molecules 2013, 18(1), 1111-1121; doi:10.3390/molecules18011111
Article

Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles

 and *
Received: 11 November 2012; in revised form: 10 January 2013 / Accepted: 10 January 2013 / Published: 16 January 2013
(This article belongs to the Special Issue Chemical Protein and Peptide Synthesis)
Download PDF [371 KB, updated 18 June 2014; original version uploaded 18 June 2014]
Abstract: Comparing a solution phase route to a solid phase route in the synthesis of the cytotoxic natural product urukthapelstatin A (Ustat A) confirmed that a solid phase method is superior. The solution phase approach was tedious and involved cyclization of a ridged heterocyclic precursor, while solid phase allowed the rapid generation of a flexible linear peptide. Cyclization of the linear peptide was facile and subsequent generation of three oxazoles located within the structure of Ustat A proved relatively straightforward. Given the ease with which the oxazole Ustat A precursor is formed via our solid phase approach, this route is amenable to rapid analog synthesis.
Keywords: urukthapelstatin A; cytotoxic; macrocycle; peptides; heterocycle; thiazole; oxazole; telomestatin; solid phase peptide synthesis urukthapelstatin A; cytotoxic; macrocycle; peptides; heterocycle; thiazole; oxazole; telomestatin; solid phase peptide synthesis
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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    Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles

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MDPI and ACS Style

Kim, S.J.; McAlpine, S.R. Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles. Molecules 2013, 18, 1111-1121.

AMA Style

Kim SJ, McAlpine SR. Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles. Molecules. 2013; 18(1):1111-1121.

Chicago/Turabian Style

Kim, Seong J.; McAlpine, Shelli R. 2013. "Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles." Molecules 18, no. 1: 1111-1121.


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