NK30424B

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Category Bioactive by-products
Catalog number BBF-03299
CAS
Molecular Weight 626.8
Molecular Formula C30H46N2O10S

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Description

NK30424B is an inhibitor of lipopolysaccharide-induced tumour necrosis factor alpha production with IC50 value of 0.9 µmol/L. It is produced by Streptomyces sp. NA30424.

Specification

IUPAC Name 2-amino-3-[[(7Z)-12-[(Z)-8-(2,6-dioxopiperidin-4-yl)-7-hydroxy-4-methyl-5-oxooct-2-en-2-yl]-10-hydroxy-9-methoxy-11-methyl-2-oxo-1-oxacyclododec-7-en-4-yl]sulfanyl]propanoic acid

Properties

Appearance White Powder
Antibiotic Activity Spectrum neoplastics (Tumor)
Melting Point 129-133°C

Reference Reading

1. Iso-migrastatin congeners from Streptomyces platensis and generation of a glutarimide polyketide library featuring the dorrigocin, lactimidomycin, migrastatin, and NK30424 scaffolds
Jianhua Ju, Si-Kyu Lim, Hui Jiang, Jeong-Woo Seo, Ben Shen J Am Chem Soc. 2005 Aug 31;127(34):11930-1. doi: 10.1021/ja053118u.
Iso-Migrastatin (10) has been shown to be the main natural product of Streptomyces platensis, which undergoes a facile, H2O-mediated rearrangement into dorrigocin A (2), 13-epi-dorrigocin A (11), dorrigocin B (3), and migrastatin (1). Eight new congeners (12-19) of 10 were characterized. They can undergo the same H2O-mediated rearrangement into the corresponding 1, 2, 3, and 11 analogues (20-43) or 1,4-Michael addition with cysteine to afford the corresponding analogues (44-51) of NK30424 A and B (5, 6). This study generated a 47-member library of glutarimide polyketides, setting the stage to investigate the SAR for this family of natural products. These results also established the absolute stereochemistry of 5 and 6 and shed new light into the post-polyketide synthase steps for 10 biosynthesis.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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