Structure and Total Synthesis of HF-7, a Neuroactive Glyconucleoside Disulfate from the Funnel-Web Spider Hololena curta

Autor:	Kevin D. McCormick, Anke K. van Engen, Gijs A. van der Marel, and Jacques H. van Boom, Bruce Ganem, Howard I. Duynstee, Yingbo Li, Jinping McCormick, Jerrold Meinwald
Rok vydání:	1999
Předmět:	Natural product Stereochemistry Total synthesis Guanosine Venom Kainate receptor General Chemistry Biochemistry Catalysis Fucose chemistry.chemical_compound Colloid and Surface Chemistry Hololena curta chemistry Ribose
Zdroj:	Journal of the American Chemical Society. 121:5661-5665
ISSN:	1520-5126 0002-7863
Popis:	Spider venom toxins have attracted considerable attention for their ability to block the action of excitatory amino acids such as glutamate and aspartate. A new neuroactive compound designated HF-7 was isolated in 1993 from the venom of a funnel-web spider, Hololena curta. HF-7 was shown to block kainate receptors and, albeit weakly, L-type calcium channels. Spectroscopic analysis established the structure of HF-7 as an unusual acetylated, disulfated fucopyranosyl guanosine, with the acetate ester attached at the 4-position of an α-linked fucose ring and two sulfates attached to the ribose ring. Because insufficient quantities of natural HF-7 were available for chemical degradation or X-ray diffraction analysis, total synthesis of three candidate structures was used to establish the identity of HF-7. Once HF-7 was fully characterized as 3‘-O-(4‘ ‘-O-acetyl-α-l-fucopyranosyl)guanosine-2‘,5‘-disulfate, an improved, targeted synthesis of the natural product was developed.
Databáze:	OpenAIRE
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