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SW-163A

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Category Bioactive by-products
Catalog number BBF-02486
CAS
Molecular Weight 670.7
Molecular Formula C34H42N2O12

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

SW-163A is an immunosuppressant isolated from the culture broth of Streptomyces sp. SNA15896. It showed immunosuppressive and antimicrobial activities in vitro.

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Synonyms SW-163 A
IUPAC Name N-(15-benzyl-10-butan-2-yl-14-hydroxy-3,7,13,13-tetramethyl-2,5,9,12-tetraoxo-1,4,8,11-tetraoxacyclopentadec-6-yl)-3-formamido-2-hydroxybenzamide
Canonical SMILES CCC(C)C1C(=O)OC(C(C(=O)OC(C(=O)OC(C(C(C(=O)O1)(C)C)O)CC2=CC=CC=C2)C)NC(=O)C3=C(C(=CC=C3)NC=O)O)C
InChI InChI=1S/C34H42N2O12/c1-7-18(2)27-32(43)45-19(3)25(36-29(40)22-14-11-15-23(26(22)38)35-17-37)31(42)46-20(4)30(41)47-24(16-21-12-9-8-10-13-21)28(39)34(5,6)33(44)48-27/h8-15,17-20,24-25,27-28,38-39H,7,16H2,1-6H3,(H,35,37)(H,36,40)
InChI Key AOOVQQYJUKCBCN-UHFFFAOYSA-N
Appearance White Powder
1. Total Synthesis of the GRP78-Downregulatory Macrolide (+)-Prunustatin A, the Immunosuppressant (+)-SW-163A, and a JBIR-04 Diastereoisomer That Confirms JBIR-04 Has Nonidentical Stereochemistry to (+)-Prunustatin A
Soraya Manaviazar, Peter Nockemann, Karl J Hale Org Lett. 2016 Jun 17;18(12):2902-5. doi: 10.1021/acs.orglett.6b01235. Epub 2016 May 27.
A unified total synthesis of the GRP78-downregulator (+)-prunustatin A and the immunosuppressant (+)-SW-163A based upon [1 + 1 + 1 + 1]-fragment condensation and macrolactonization between O(4) and C(5) is herein described. Sharpless asymmetric dihydroxylation was used to set the C(2) stereocenter present in both targets. In like fashion, coupling of the (+)-prunustatin A macrolide amine with benzoic acid furnished a JBIR-04 diastereoisomer whose NMR spectra did not match those of JBIR-04, thus confirming that it has different stereochemistry than (+)-prunustatin A.
2. 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 Org Lett. 2007 Oct 11;9(21):4239-42. doi: 10.1021/ol7017856. Epub 2007 Sep 21.
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.
3. Novel GRP78 molecular chaperone expression down-regulators JBIR-04 and -05 isolated from Streptomyces violaceoniger
Miho Izumikawa, Jun-ya Ueda, Shuhei Chijiwa, Motoki Takagi, Kazuo Shin-ya J Antibiot (Tokyo). 2007 Oct;60(10):640-4. doi: 10.1038/ja.2007.82.
In the course of our screening program for regulators of the expression of GRP78 molecular chaperone, JBIR-04 (1) and -05 (2) were isolated from Streptomyces violaceoniger 4541-SVS3 as congeners of prunustatin A (3). The structures of 1 and 2 were determined by the analyses of the spectroscopic data. These compounds mainly consist of an amino acid and amino acid derived alpha-hydroxy acid residues. 1 and 2 inhibited the expression of GRP78 induced by 2-deoxyglucose in human fibrosarcoma HT1080 cells, but their activities were highly reduced compared with those of 3 and SW-163A.

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