Relative and absolute configuration of versipelostatin, a down-regulator of molecular chaperone GRP78 expression.
[structure: see text] Versipelostatin is the first compound which specifically inhibits the expression of GRP78 and the resultant robust cell death under stress conditions, in contrast to the weak cytotoxicity under normal conditions. Versipelostatin consists of a macrocyclic aglycone with an alpha-acyltetronic acid and three sugar moieties. The relative and absolute configuration of the aglycone moiety was established to be 4S, 5S, 6R, 9S, 10S, 13S, 16R, 18R, 19R, 20R, 24R, 27R, and 29S utilizing NMR techniques.
Park
Hae-Ryong
HR
Institute of Molecular and Cellular Biosciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-0032, Japan.
Chijiwa
Shuhei
S
Furihata
Kazuo
K
Hayakawa
Yoichi
Y
Shin-Ya
Kazuo
K
D003510:Cyclohexanes / Q000737:chemistry; D015536:Down-Regulation / Q000187:drug effects*; D000091342:Endoplasmic Reticulum Chaperone BiP; D006360:Heat-Shock Proteins / Q000096:biosynthesis* / Q000235:genetics; D018942:Macrolides / Q000737:chemistry* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D018832:Molecular Chaperones / Q000096:biosynthesis* / Q000235:genetics; D015394:Molecular Structure; D009844:Oligosaccharides / Q000737:chemistry* / Q000494:pharmacology*
D003510:Cyclohexanes; D000091342:Endoplasmic Reticulum Chaperone BiP; D006360:Heat-Shock Proteins; D018942:Macrolides; D018832:Molecular Chaperones; D009844:Oligosaccharides; C490154:versipelostatin; C506365:Cyclohexane