Altemicidin

Altemicidin

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Altemicidin
Category Antibiotics
Catalog number BBF-00424
CAS 125399-82-8
Molecular Weight 376.38
Molecular Formula C13H20N4O7S
Purity 99%

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Description

It is produced by the strain of Streptomyces sioyaensis. It has acaricidal and anti-tumor activity. The inhibition IC50 of L1210 and IMC cancer cells was 0.84 and 0.82 ㎍/mL.

Specification

Synonyms CTK4B4358; DTXSID20925120; 1H-Cyclopenta[c]pyridine-7-carboxylicacid,4-(aminocarbonyl)-7-[[2-(aminosulfonyl)acetyl]amino]-2,4a,5,6,7,7a-hexahydro-6-hydroxy-2-methyl-,(4aR,6S,7R,7aS)-; LS-136376; Q15410226; 6-Hydroxy-7-({[(1-hydroxy-2-sulfamoylethylidene)amino]oxy}carbonyl)-2-methyl-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridine-4-carboximidic acid
IUPAC Name [(2-sulfamoylacetyl)amino] (4aR,6S,7R,7aS)-4-carbamoyl-6-hydroxy-2-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyridine-7-carboxylate
Canonical SMILES CN1CC2C(CC(C2C(=O)ONC(=O)CS(=O)(=O)N)O)C(=C1)C(=O)N
InChI InChI=1S/C13H20N4O7S/c1-17-3-7-6(8(4-17)12(14)20)2-9(18)11(7)13(21)24-16-10(19)5-25(15,22)23/h4,6-7,9,11,18H,2-3,5H2,1H3,(H2,14,20)(H,16,19)(H2,15,22,23)/t6-,7+,9+,11-/m1/s1
InChI Key FIVJGKCWTLGNQR-VFYMIVFZSA-N

Properties

Appearance White Powder
Antibiotic Activity Spectrum neoplastics (Tumor)
Melting Point 195-199 °C (dec.)
Density 1.547 g/cm3
Solubility Soluble in Water, Hydrochloric acid, Sodium hydroxide

Reference Reading

1. Toward the Synthesis of SB-203207: Construction of Four Contiguous Nitrogen-Containing Stereogenic Centers
Ichiro Hayakawa, Anna Nagayasu, Akira Sakakura J Org Chem. 2019 Dec 6;84(23):15614-15623. doi: 10.1021/acs.joc.9b02627. Epub 2019 Nov 20.
SB-203207 is an altemicidin-type alkaloid that potently inhibits isoleucyl tRNA synthetase activity. Its main structural feature is a hexahydro-6-azaindene framework containing a unique β-hydroxy α,α-disubstituted α-amino acid moiety on the cyclopentane portion. Herein we have established a method for constructing the four contiguous nitrogen-containing stereogenic centers of SB-203207 by using as key steps the stereoselective alkylation of bowl-shaped tricyclic lactone to construct a quaternary carbon at C1, the stereoselective hydroboration-oxidation reaction to install the C2 hydroxy group, and the Curtius rearrangement to introduce a nitrogen atom onto the C1 quaternary carbon.
2. Dearomative Synthetic Entry into the Altemicidin Alkaloids
Claire S Harmange Magnani, Thomas J Maimone J Am Chem Soc. 2021 Jun 2;143(21):7935-7939. doi: 10.1021/jacs.1c04147. Epub 2021 May 21.
Altemicidin and related Streptomyces-derived monoterpene alkaloids possess dense, highly polar azaindane cores as well as potent cytotoxic and tRNA synthetase inhibitory properties. The congested α-amino acid motif decorating their presumed iridoid-like core structure has proven to be both a synthetic challenge and a biosynthetic mystery to date. Herein, we report a distinct, abiotic strategy to these alkaloids resulting in a concise synthesis of altemicidin from simple chemical feedstocks. Key chemical findings include the exploitation of a dearomative pyridinium addition and dipolar cycloaddition sequence to stereospecifically install the quaternary amine moiety, and a chemoselective molybdenum-mediated double reduction to establish the fully functionalized azaindane nucleus with minimal redox manipulations.
3. Aminoacyl sulfonamide assembly in SB-203208 biosynthesis
Zhijuan Hu, Takayoshi Awakawa, Zhongjun Ma, Ikuro Abe Nat Commun. 2019 Jan 14;10(1):184. doi: 10.1038/s41467-018-08093-x.
Sulfonamide is present in many important drugs, due to its unique chemical and biological properties. In contrast, naturally occurring sulfonamides are rare, and their biosynthetic knowledge are scarce. Here we identify the biosynthetic gene cluster of sulfonamide antibiotics, altemicidin, SB-203207, and SB-203208, from Streptomyces sp. NCIMB40513. The heterologous gene expression and biochemical analyses reveal unique aminoacyl transfer reactions, including the tRNA synthetase-like enzyme SbzA-catalyzed L-isoleucine transfer and the GNAT enzyme SbzC-catalyzed β-methylphenylalanine transfer. Furthermore, we elucidate the biogenesis of 2-sulfamoylacetic acid from L-cysteine, by the collaboration of the cupin dioxygenase SbzM and the aldehyde dehydrogenase SbzJ. Remarkably, SbzM catalyzes the two-step oxidation and decarboxylation of L-cysteine, and the subsequent intramolecular amino group rearrangement leads to N-S bond formation. This detailed analysis of the aminoacyl sulfonamide antibiotics biosynthetic machineries paves the way toward investigations of sulfonamide biosynthesis and its engineering.

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