Solid Phase versus Solution Phase Synthesis of  Heterocyclic Macrocycles

doi:10.3390/molecules18011111

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

Article

Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles

Seong Jong Kim and Shelli R. McAlpine*

School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia

* Author to whom correspondence should be addressed.

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)

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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

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Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles

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Cite This Article

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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