Absolute structure of prunustatin A, a novel GRP78 molecular chaperone down-regulator

Yukiko Umeda; Kazuo Furihata; Shohei Sakuda; Hiromichi Nagasawa; Ken Ishigami; Hidenori Watanabe; Miho Izumikawa; Motoki Takagi; Takayuki Doi; Yoichi Nakao; Kazuo Shin-ya

doi:10.1021/ol7017856

Absolute structure of prunustatin A, a novel GRP78 molecular chaperone down-regulator

Yukiko Umeda, Kazuo Furihata, Shohei Sakuda, Hiromichi Nagasawa, Ken Ishigami, Hidenori Watanabe, Miho Izumikawa, Motoki Takagi, Takayuki Doi, Yoichi Nakao, Kazuo Shin-ya^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

27 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	4239-4242
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	21
DOIs	https://doi.org/10.1021/ol7017856
Publication status	Published - 2007 Oct 11

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol7017856

Cite this

@article{e8771bc97d3f4a428a4cb07c4dc0ab40,

title = "Absolute structure of prunustatin A, a novel GRP78 molecular chaperone down-regulator",

abstract = "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.",

author = "Yukiko Umeda and Kazuo Furihata and Shohei Sakuda and Hiromichi Nagasawa and Ken Ishigami and Hidenori Watanabe and Miho Izumikawa and Motoki Takagi and Takayuki Doi and Yoichi Nakao and Kazuo Shin-ya",

year = "2007",

month = oct,

day = "11",

doi = "10.1021/ol7017856",

language = "English",

volume = "9",

pages = "4239--4242",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Absolute structure of prunustatin A, a novel GRP78 molecular chaperone down-regulator

AU - Umeda, Yukiko

AU - Furihata, Kazuo

AU - Sakuda, Shohei

AU - Nagasawa, Hiromichi

AU - Ishigami, Ken

AU - Watanabe, Hidenori

AU - Izumikawa, Miho

AU - Takagi, Motoki

AU - Doi, Takayuki

AU - Nakao, Yoichi

AU - Shin-ya, Kazuo

PY - 2007/10/11

Y1 - 2007/10/11

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=35548994250&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=35548994250&partnerID=8YFLogxK

U2 - 10.1021/ol7017856

DO - 10.1021/ol7017856

M3 - Article

C2 - 17887691

AN - SCOPUS:35548994250

SN - 1523-7060

VL - 9

SP - 4239

EP - 4242

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Absolute structure of prunustatin A, a novel GRP78 molecular chaperone down-regulator

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this