Absolute structure of prunustatin A, a novel GRP78 molecular chaperone down-regulator.
In the course of our screening program for regulators of a molecular chaperone GRP78 expression, we isolated a novel inhibitor of GRP78 expression, designated as prunustatin A, from Streptomyces violaceoniger 4521-SVS3. The planar structure of prunustatin A was determined to be an oxidized type of the neoantimycin family. Its absolute stereochemistry was established to be 2R, 4S, 6S, 7R, 9S, and 29S by analyzing chemically degraded components obtained from the derivative of prunustatin A.
Umeda
Yukiko
Y
Graduate School of Agricultural and Life Sciences, The University of Tokyo, Tokyo 113-8657, Japan.
Furihata
Kazuo
K
Sakuda
Shohei
S
Nagasawa
Hiromichi
H
Ishigami
Ken
K
Watanabe
Hidenori
H
Izumikawa
Miho
M
Takagi
Motoki
M
Doi
Takayuki
T
Nakao
Yoichi
Y
Shin-ya
Kazuo
K
D000091342:Endoplasmic Reticulum Chaperone BiP; D005947:Glucose / Q000378:metabolism; D006360:Heat-Shock Proteins / Q000187:drug effects* / Q000378:metabolism; D006801:Humans; D018942:Macrolides / Q000737:chemistry* / Q000494:pharmacology*; D018832:Molecular Chaperones / Q000187:drug effects* / Q000378:metabolism; D015394:Molecular Structure; D009930:Organic Chemicals / Q000737:chemistry; D010456:Peptides, Cyclic / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry*; D014407:Tumor Cells, Cultured
D000091342:Endoplasmic Reticulum Chaperone BiP; C000717247:HSPA5 protein, human; D006360:Heat-Shock Proteins; D018942:Macrolides; D018832:Molecular Chaperones; D009930:Organic Chemicals; D010456:Peptides, Cyclic; C447401:SW-163A; C501241:prunustatin A; C002699:neoantimycin; D005947:Glucose