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 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.
Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China.
Qianjiao
Q
Yang
Dan
D
Liu
Deyang
D
Sun
Sen
S
Yang
Guodong
G
Hu
Zuti
Z
Wu
Linxiang
L
Zhao
D000818:Animals; D018360:Crystallography, X-Ray; D004220:Disulfides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D004220:Disulfides; C475724:bromotyrosine; C556444:psammaplin F; C098378:psammaplin A; D014443:Tyrosine