Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue

Psammaplin F, an unsymmetrical disulfide bromotyrosine, was isolated from the sponge Pseudoceratina purpurea in 2003. We reported here the first total synthesis of psammaplin F in 12% overall yield by employing Cleland’s reagent reduction as key step. The longest linear synthetic sequence starting f...

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Detalles Bibliográficos
Autores principales: Yang, Qianjiao, Liu, Dan, Sun, Deyang, Yang, Sen, Hu, Guodong, Wu, Zuti, Zhao, Linxiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6259465/
https://www.ncbi.nlm.nih.gov/pubmed/21127464
http://dx.doi.org/10.3390/molecules15128784
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author Yang, Qianjiao
Liu, Dan
Sun, Deyang
Yang, Sen
Hu, Guodong
Wu, Zuti
Zhao, Linxiang
author_facet Yang, Qianjiao
Liu, Dan
Sun, Deyang
Yang, Sen
Hu, Guodong
Wu, Zuti
Zhao, Linxiang
author_sort Yang, Qianjiao
collection PubMed
description Psammaplin F, an unsymmetrical disulfide bromotyrosine, was isolated from the sponge Pseudoceratina purpurea in 2003. We reported here the first total synthesis of psammaplin F in 12% overall yield by employing Cleland’s reagent reduction as key step. The longest linear synthetic sequence starting from 3-bromo-4-hydroxybenzaldehyde and hydantoin was seven steps. In addition, a detailed X-ray crystal structure analysis of psammaplin A analogue 8b is given for the first time.
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spelling pubmed-62594652018-12-06 Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue Yang, Qianjiao Liu, Dan Sun, Deyang Yang, Sen Hu, Guodong Wu, Zuti Zhao, Linxiang Molecules Article Psammaplin F, an unsymmetrical disulfide bromotyrosine, was isolated from the sponge Pseudoceratina purpurea in 2003. We reported here the first total synthesis of psammaplin F in 12% overall yield by employing Cleland’s reagent reduction as key step. The longest linear synthetic sequence starting from 3-bromo-4-hydroxybenzaldehyde and hydantoin was seven steps. In addition, a detailed X-ray crystal structure analysis of psammaplin A analogue 8b is given for the first time. MDPI 2010-12-02 /pmc/articles/PMC6259465/ /pubmed/21127464 http://dx.doi.org/10.3390/molecules15128784 Text en © 2010 by the authors; http://creativecommons.org/licenses/by/3.0/ 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
Yang, Qianjiao
Liu, Dan
Sun, Deyang
Yang, Sen
Hu, Guodong
Wu, Zuti
Zhao, Linxiang
Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue
title Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue
title_full Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue
title_fullStr Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue
title_full_unstemmed Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue
title_short Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue
title_sort synthesis of the marine bromotyrosine psammaplin f and crystal structure of a psammaplin a analogue
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6259465/
https://www.ncbi.nlm.nih.gov/pubmed/21127464
http://dx.doi.org/10.3390/molecules15128784
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