Sulfazecin
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| Category | Others |
| Catalog number | BBF-03087 |
| CAS | 77912-79-9 |
| Molecular Weight | 396.38 |
| Molecular Formula | C12H20N4O9S |
| Purity | >98% |
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Description
Sulfazecin is a water-soluble acidic substance produced by Pseudomonas acidophila G 6302. It has anti-Gram-negative bacteria activity and weak anti-Gram-positive bacteria activity.
Specification
| Storage | Store at -20°C |
| IUPAC Name | (2R)-2-amino-5-[[(2R)-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-/m1/s1 |
| InChI Key | MOBOUQJWGBVNCR-NQYJQULFSA-N |
Properties
| Appearance | Colorless Needle Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Melting Point | 168-170°C(dec.) |
| Density | 1.628 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. 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.
2. Identification and Characterization of the Sulfazecin Monobactam Biosynthetic Gene Cluster
Rongfeng Li, Ryan A Oliver, Craig A Townsend Cell Chem Biol. 2017 Jan 19;24(1):24-34. doi: 10.1016/j.chembiol.2016.11.010. Epub 2016 Dec 22.
The monobactams, exemplified by the natural product sulfazecin, are the only class of β-lactam antibiotics not inactivated by metallo-β-lactamases, which confer bacteria with extended-spectrum β-lactam resistance. We screened a transposon mutagenesis library from Pseudomonas acidophila ATCC 31363 and isolated a sulfazecin-deficient mutant that revealed a gene cluster encoding two non-ribosomal peptide synthetases (NRPSs), a methyltransferase, a sulfotransferase, and a dioxygenase. Three modules and an aberrant C-terminal thioesterase (TE) domain are distributed across the two NRPSs. Biochemical examination of the adenylation (A) domains provided evidence that L-2,3-diaminopropionate, not L-serine as previously thought, is the direct source of the β-lactam ring of sulfazecin. ATP/PPi exchange assay also revealed an unusual substrate selectivity shift of one A domain when expressed with or without the immediately upstream condensation domain. Gene inactivation analysis defined a cluster of 13 open reading frames sufficient for sulfazecin production, precursor synthesis, self-resistance, and regulation. The identification of a key intermediate supported a proposed NRPS-mediated mechanism of sulfazecin biosynthesis and β-lactam ring formation distinct from the nocardicins, another NRPS-derived subclass of monocyclic β-lactam. These findings will serve as the basis for further biosynthetic research and potential engineering of these important antibiotics.
3. One Ring to Fight Them All: The Sulfazecin Story
Daniel Braga, Gerald Lackner Cell Chem Biol. 2017 Jan 19;24(1):1-2. doi: 10.1016/j.chembiol.2017.01.001.
In this issue of Cell Chemical Biology, Li et al. (2017) report on the biosynthesis of the monobactam sulfazecin by Pseudomonas acidophila and hypothesize a novel mechanism of β-lactam ring formation. As monobactam antibiotics are unaffected by some emerging resistance mechanisms (particularly metallo-β-lactamases), this discovery opens prospects to engineer β-lactam antibiotics against multi-drug resistant pathogens.
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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 ╳
