Isosulfazecin
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| Category | Antibiotics |
| Catalog number | BBF-01514 |
| CAS | 77900-75-5 |
| Molecular Weight | 396.38 |
| Molecular Formula | C12H20N4O9S |
| Purity | >98% |
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Description
Isosulfazecin is a beta-lactam antibiotic produced by the strain of Pseudomonas mesoacidophila sp. nov. Its anti-gram-positive bacteria effect is similar to SZ (Sulfazecin), but its anti-gram-negative bacteria activity is weaker than SZ.
Specification
| Synonyms | (R)-D-gamma-Glutamyl-N-(3-methoxy-2-oxo-1-sulfo-3-azetidinyl)-L-alaninamide; (3R)-2-Oxo-3-methoxy-3beta-[[N-[(4R)-4-amino-4-carboxybutyryl]alanyl]amino]azetidine-1-sulfonic acid |
| IUPAC Name | (2R)-2-amino-5-[[(2S)-1-[[(3R)-3-methoxy-2-oxo-1-sulfoazetidin-3-yl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid |
| Canonical SMILES | CC(C(=O)NC1(CN(C1=O)S(=O)(=O)O)OC)NC(=O)CCC(C(=O)O)N |
| InChI | InChI=1S/C12H20N4O9S/c1-6(14-8(17)4-3-7(13)10(19)20)9(18)15-12(25-2)5-16(11(12)21)26(22,23)24/h6-7H,3-5,13H2,1-2H3,(H,14,17)(H,15,18)(H,19,20)(H,22,23,24)/t6-,7+,12+/m0/s1 |
| InChI Key | MOBOUQJWGBVNCR-QRPMWFLTSA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Density | 1.62 g/cm3 |
Reference Reading
1. Whole-Genome Shotgun Sequencing of Two β-Proteobacterial Species in Search of the Bulgecin Biosynthetic Cluster
Mark E Horsman, Daniel R Marous, Rongfeng Li, Ryan A Oliver, Byungjin Byun, Scott J Emrich, Bill Boggess, Craig A Townsend, Shahriar Mobashery ACS Chem Biol. 2017 Oct 20;12(10):2552-2557. doi: 10.1021/acschembio.7b00687. Epub 2017 Sep 26.
We have produced draft whole-genome sequences for two bacterial strains reported to produce the bulgecins as well as NRPS-derived monobactam β-lactam antibiotics. We propose classification of ATCC 31363 as Paraburkholderia acidophila. We further reaffirm that ATCC 31433 (Burkholderia ubonensis subsp. mesacidophila) is a taxonomically distinct producer of bulgecins with notable gene regions shared with Paraburkholderia acidophila. We use RAST multiple-gene comparison and MASH distancing with published genomes to order the draft contigs and identify unique gene regions for characterization. Forty-eight natural-product gene clusters are presented from PATRIC (RASTtk) and antiSMASH annotations. We present evidence that the 10 genes that follow the sulfazecin and isosulfazecin pathways in both species are likely involved in bulgecin A biosynthesis.
2. Reclassification of the Specialized Metabolite Producer Pseudomonas mesoacidophila ATCC 31433 as a Member of the Burkholderia cepacia Complex
E Joel Loveridge, Cerith Jones, Matthew J Bull, Suzy C Moody, Małgorzata W Kahl, Zainab Khan, Louis Neilson, Marina Tomeva, Sarah E Adams, Andrew C Wood, Daniel Rodriguez-Martin, Ingrid Pinel, Julian Parkhill, Eshwar Mahenthiralingam, John Crosby J Bacteriol. 2017 Jun 13;199(13):e00125-17. doi: 10.1128/JB.00125-17. Print 2017 Jul 1.
Pseudomonas mesoacidophila ATCC 31433 is a Gram-negative bacterium, first isolated from Japanese soil samples, that produces the monobactam isosulfazecin and the β-lactam-potentiating bulgecins. To characterize the biosynthetic potential of P. mesoacidophila ATCC 31433, its complete genome was determined using single-molecule real-time DNA sequence analysis. The 7.8-Mb genome comprised four replicons, three chromosomal (each encoding rRNA) and one plasmid. Phylogenetic analysis demonstrated that P. mesoacidophila ATCC 31433 was misclassified at the time of its deposition and is a member of the Burkholderia cepacia complex, most closely related to Burkholderia ubonensis The sequenced genome shows considerable additional biosynthetic potential; known gene clusters for malleilactone, ornibactin, isosulfazecin, alkylhydroxyquinoline, and pyrrolnitrin biosynthesis and several uncharacterized biosynthetic gene clusters for polyketides, nonribosomal peptides, and other metabolites were identified. Furthermore, P. mesoacidophila ATCC 31433 harbors many genes associated with environmental resilience and antibiotic resistance and was resistant to a range of antibiotics and metal ions. In summary, this bioactive strain should be designated B. cepacia complex strain ATCC 31433, pending further detailed taxonomic characterization.IMPORTANCE This work reports the complete genome sequence of Pseudomonas mesoacidophila ATCC 31433, a known producer of bioactive compounds. Large numbers of both known and novel biosynthetic gene clusters were identified, indicating that P. mesoacidophila ATCC 31433 is an untapped resource for discovery of novel bioactive compounds. Phylogenetic analysis demonstrated that P. mesoacidophila ATCC 31433 is in fact a member of the Burkholderia cepacia complex, most closely related to the species Burkholderia ubonensis Further investigation of the classification and biosynthetic potential of P. mesoacidophila ATCC 31433 is warranted.
3. Monobactam formation in sulfazecin by a nonribosomal peptide synthetase thioesterase
Ryan A Oliver, Rongfeng Li, Craig A Townsend Nat Chem Biol. 2018 Jan;14(1):5-7. doi: 10.1038/nchembio.2526. Epub 2017 Nov 20.
The N-sulfonated monocyclic β-lactam ring characteristic of the monobactams confers resistance to zinc metallo-β-lactamases and affords the most effective class to combat carbapenem-resistant enterobacteria (CRE). Here we report unprecedented nonribosomal peptide synthetase activities, wherein an assembled tripeptide is N-sulfonated in trans before direct synthesis of the β-lactam ring in a noncanonical, cysteine-containing thioesterase domain. This means of azetidinone synthesis is distinct from the three others known in nature.
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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 ╳
