synthesis of the marine bromotyrosine psammaplin f and crystal structure of a psammaplin a analogue合成海洋bromotyrosine psammaplin psammaplin f和晶体结构的模拟.pdfVIP

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synthesis of the marine bromotyrosine psammaplin f and crystal structure of a psammaplin a analogue合成海洋bromotyrosine psammaplin psammaplin f和晶体结构的模拟.pdf

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synthesis of the marine bromotyrosine psammaplin f and crystal structure of a psammaplin a analogue合成海洋bromotyrosine psammaplin psammaplin f和晶体结构的模拟

Molecules 2010, 15, 8784-8795; doi: 10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue Qianjiao Yang, Dan Liu, Deyang Sun, Sen Yang, Guodong Hu, Zuti Wu and Linxiang Zhao * Key Laboratory of Structure-Based Drug Design Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China * Author to whom correspondence should be addressed; E-Mail: zhaolinxiang@; Tel.: +86-24-2398-6420; Fax: +86-24-2398-6420. Received: 4 November 2010; in revised form: 25 November 2010 / Accepted: 29 November 2010 / Published: 2 December 2010 Abstract: 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. Keywords: psammaplin F; marine bromotyrosine; Cleland’s reagent; total synthesis; X-ray crystal structure 1. Introduction The psammaplin disulfide bromotyrosine derivatives exhibit wide-ranging biological activities including anticancer activity [1,2], anti methicillin-resistant Staphylococcus aureus (MRSA) a