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Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles
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 pha...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6269862/ https://www.ncbi.nlm.nih.gov/pubmed/23325099 http://dx.doi.org/10.3390/molecules18011111 |
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author | Kim, Seong Jong McAlpine, Shelli R. |
author_facet | Kim, Seong Jong McAlpine, Shelli R. |
author_sort | Kim, Seong Jong |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-6269862 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62698622018-12-14 Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles Kim, Seong Jong McAlpine, Shelli R. Molecules Article 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. MDPI 2013-01-16 /pmc/articles/PMC6269862/ /pubmed/23325099 http://dx.doi.org/10.3390/molecules18011111 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Kim, Seong Jong McAlpine, Shelli R. Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles |
title | Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles |
title_full | Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles |
title_fullStr | Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles |
title_full_unstemmed | Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles |
title_short | Solid Phase versus Solution Phase Synthesis of Heterocyclic Macrocycles |
title_sort | solid phase versus solution phase synthesis of heterocyclic macrocycles |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6269862/ https://www.ncbi.nlm.nih.gov/pubmed/23325099 http://dx.doi.org/10.3390/molecules18011111 |
work_keys_str_mv | AT kimseongjong solidphaseversussolutionphasesynthesisofheterocyclicmacrocycles AT mcalpineshellir solidphaseversussolutionphasesynthesisofheterocyclicmacrocycles |