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Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue
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.
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
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MDPI and ACS Style
Yang, Q.; Liu, D.; Sun, D.; Yang, S.; Hu, G.; Wu, Z.; Zhao, L. Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue. Molecules 2010, 15, 8784-8795.
Yang Q, Liu D, Sun D, Yang S, Hu G, Wu Z, Zhao L. Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue. Molecules. 2010; 15(12):8784-8795.
Yang, Qianjiao; Liu, Dan; Sun, Deyang; Yang, Sen; Hu, Guodong; Wu, Zuti; Zhao, Linxiang. 2010. "Synthesis of the Marine Bromotyrosine Psammaplin F and Crystal Structure of a Psammaplin A Analogue." Molecules 15, no. 12: 8784-8795.