SB-203208
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03400 |
| CAS | |
| Molecular Weight | 650.7 |
| Molecular Formula | C29H42N6O9S |
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Description
SB-203208 is a tRNA synthetase inhibitor produced by Streptomyces sp. NCIMB 40513.
Specification
| Synonyms | SB 203208; SB203208 |
| IUPAC Name | (4aR,6S,7R,7aS)-7-[[2-[[(2S,3S)-2-amino-3-methylpentanoyl]sulfamoyl]acetyl]amino]-6-[(2S,3S)-2-amino-3-phenylbutanoyl]oxy-4-carbamoyl-2-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyridine-7-carboxylic acid |
| Canonical SMILES | CCC(C)C(C(=O)NS(=O)(=O)CC(=O)NC1(C(CC2C1CN(C=C2C(=O)N)C)OC(=O)C(C(C)C3=CC=CC=C3)N)C(=O)O)N |
| InChI | InChI=1S/C29H42N6O9S/c1-5-15(2)23(30)26(38)34-45(42,43)14-22(36)33-29(28(40)41)20-13-35(4)12-19(25(32)37)18(20)11-21(29)44-27(39)24(31)16(3)17-9-7-6-8-10-17/h6-10,12,15-16,18,20-21,23-24H,5,11,13-14,30-31H2,1-4H3,(H2,32,37)(H,33,36)(H,34,38)(H,40,41)/t15-,16-,18-,20+,21-,23-,24-,29+/m0/s1 |
| InChI Key | UEPCEXDSBHEBAB-DLKTYGRBSA-N |
Properties
| Appearance | Colorless Powder |
Reference Reading
1. Engineered Biosynthesis of Pharmaceutically Important Compounds
Takayoshi Awakawa Chem Pharm Bull (Tokyo). 2021;69(5):415-420. doi: 10.1248/cpb.c21-00032.
Natural products are an important source of medicinal seeds. The discovery of novel biosynthetic enzymes from nature is important for their use as biocatalysts for the enzymatic synthesis of useful natural products. In addition, genetics and structural biology developments have enabled the engineering of enzymes for the production of unnatural analogs of bioactive natural products. In this review, I describe the recent research on these two topics, the exploitation of a novel secondary metabolite enzyme involved in the biosynthesis of the sulfonamide natural product antibiotic SB-203208, and the production of unnatural bioactive depsipeptides by reconstruction of the modular enzyme assembly lines in the microbial host.
2. Biosynthesis of sulfonamide and sulfamate antibiotics in actinomycete
Takayoshi Awakawa, Lena Barra, Ikuro Abe J Ind Microbiol Biotechnol. 2021 Jun 4;48(3-4):kuab001. doi: 10.1093/jimb/kuab001.
Sulfonamides and sulfamates are a group of organosulfur compounds that contain the signature sulfamoyl structural motif. These compounds were initially only known as synthetic antibacterial drugs but were later also discovered as natural products. Eight highly potent examples have been isolated from actinomycetes to date, illustrating the large biosynthetic repertoire of this bacterial genus. For the biosynthesis of these compounds, several distinct and unique biosynthetic machineries have been discovered, capable to generate the unique S-N bond. For the creation of novel, second generation natural products by biosynthetic engineering efforts, a detailed understanding of the underlying enzyme machinery toward potent structural motifs is crucial. In this review, we aim to summarize the current state of knowledge on sulfonamide and sulfamate biosynthesis. A detailed discussion for the secondary sulfamate ascamycin, the tertiary sulfonamide sulfadixiamycin A, and the secondary sulfonamide SB-203208 is provided and their bioactivities and mode of actions are discussed.
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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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
