Cephalosporin C
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| Category | Antibiotics |
| Catalog number | BBF-00758 |
| CAS | 61-24-5 |
| Molecular Weight | 415.42 |
| Molecular Formula | C16H21N3O8S |
| Purity | 95% |
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Description
It is produced by the strain of Cephalosporium aceemonium C.M.I 49137. Cephalosporin C has weak resistance to gram-positive and negative bacteria, is stable to penicillinase, and can be broken down by cephalosporin enzyme. Hydrolysis and removal of side chains to obtain 7-amino-cefenoic acid (7-ACA) is an important raw material for the preparation of semi-synthetic cephalosporin.
Specification
| Related CAS | 51762-04-0 (sodium salt) 57847-70-8 (potassium salt) 59143-60-1 (mono-zinc salt) |
| Synonyms | 7-(5-Amino-5-carboxyvaleramido)cephalosporanic acid; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-7-((5-amino-5-carboxy-1-oxopentyl)amino)-8-oxo-, (6R-(6alpha,7beta(R*)))-; Centpropazine; Cephalosporin; Cephalosporn C |
| IUPAC Name | (6R,7R)-3-(acetyloxymethyl)-7-[[(5R)-5-amino-5-carboxypentanoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Canonical SMILES | CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CCCC(C(=O)O)N)SC1)C(=O)O |
| InChI | InChI=1S/C16H21N3O8S/c1-7(20)27-5-8-6-28-14-11(13(22)19(14)12(8)16(25)26)18-10(21)4-2-3-9(17)15(23)24/h9,11,14H,2-6,17H2,1H3,(H,18,21)(H,23,24)(H,25,26)/t9-,11-,14-/m1/s1 |
| InChI Key | HOKIDJSKDBPKTQ-GLXFQSAKSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 814.7±65.0 °C (Predicted) |
| Density | 1.55±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Water; Hardly soluble in organic solvents |
Reference Reading
1.Unveiling the Atomic-Level Determinants of Acylase-Ligand Complexes: An Experimental and Computational Study.
Mollica L1, Conti G2, Pollegioni L2,3, Cavalli A1,4, Rosini E2,3. J Chem Inf Model. 2015 Oct 26;55(10):2227-41. doi: 10.1021/acs.jcim.5b00535. Epub 2015 Sep 30.
The industrial production of higher-generation semisynthetic cephalosporins starts from 7-aminocephalosporanic acid (7-ACA), which is obtained by deacylation of the naturally occurring antibiotic cephalosporin C (CephC). The enzymatic process in which CephC is directly converted into 7-ACA by a cephalosporin C acylase has attracted industrial interest because of the prospects of simplifying the process and reducing costs. We recently enhanced the catalytic efficiency on CephC of a glutaryl acylase from Pseudomonas N176 (named VAC) by a protein engineering approach and solved the crystal structures of wild-type VAC and the H57βS-H70βS VAC double variant. In the present work, experimental measurements on several CephC derivatives and six VAC variants were carried out, and the binding of ligands into the VAC active site was investigated at an atomistic level by means of molecular docking and molecular dynamics simulations and analyzed on the basis of the molecular geometry of encounter complex formation and protein-ligand potential of mean force profiles.
2.Feasibility study of recycling cephalosporin C fermentation dregs using co-composting process with activated sludge as co-substrate.
Chen Z1, Wang Y1, Wen Q1, Zhang S1, Yang L1. Environ Technol. 2016 Mar 7:1-9. [Epub ahead of print]
Composting is a potential alternative for cephalosporin C fermentation dregs (CCFDs) compared with incineration process or landfill because of its advantage of recovering nutrients. In this research, CCFDs and activated sludge (AS) were co-composted to analyze the feasibility of recycling the nutrients in CCFDs. A pilot-scale aerobic composting system with an auto-control system was used in this research, and the maturity and security of the compost product were evaluated. The temperature of the composting mixtures was maintained above 55°C for more than 3 days during the composting, indicating that co-composting of CCFDs and AS could reach the compost maturity standard, and the seeds germination index (GI) increased from 17.61% to 68.93% by the end of the composting process (28 days). However, the degradation rate of cephalosporin C (CPC) was only 6.58% during the composting process. Monitoring the quality of antibiotic resistance genes (ARGs) in the composts showed that the log copy of blaTEM in the composts increased from 2.
3.Comparative expression profiling of genes involved in primary metabolism in high-yield and wild-type strains of Acremonium chrysogenum.
Han S1,2, Liu Y2, Xie L2, Zhu B1, Hu Y3. Antonie Van Leeuwenhoek. 2016 Mar;109(3):357-69. doi: 10.1007/s10482-015-0638-5. Epub 2015 Dec 28.
Cephalosporin C (CPC) productivity of Acremonium chrysogenum has been improved significantly through classical strain improvement programs. Here, we used transcription and metabolite profiling to address mechanisms underlying CPC production in a high yield (HY) strain. Transcription and metabolite profiling indicated that enzymes involved in amino acid production are higher in abundance in the HY strain. Moreover, results indicate a higher flow of precursors from the glycolysis and gluconeogenesis pathways to serine synthesis at the late stage of fermentation in the HY strain. In addition, less pyruvate would enter the TCA cycle thus favoring valine synthesis. Amino acid production would also benefit from a more active pentose phosphate pathway and γ-amino butyric acid shunt both generating NADPH. Moreover the glyoxylate pathway seems to be more active in the HY strain. These results may provide new leads for CPC strain improvement in industry.
4.[Recombinant cephalosporin-acid synthesase: optimisation of expression in E.coli cells, immobilisation and application for biocatalytic cefazolin synthesis].
Eldarov MA1, Sklyarenko AV2, Dumina MV1, Medvedeva NV2, Jgoun AA1, Satarova JE2, Sidorenko AI2, Emperian AS3, Yarotsky SV2. Biomed Khim. 2015 Sep-Oct;61(5):646-51. doi: 10.18097/PBMC20156105646.
in
English, RussianSintetaza tsefalosporinov-kislot (cephalosporin-acid synthetase, CASA) spetsifichna k sintezu tsefalosporinov-kislot; produktsiia étogo fermenta v kletkakh Escherichia coli soprovozhdaetsia nakopleniem neprotsessirovannogo nerastvorimogo predshestvennika. Dlia optimizatsii usloviĭ produktsii rekombinantnoĭ CASA izuchali éffekty takikh parametrov kul'tivirovaniia shtamma-produtsenta kak sostav pitatel'noĭ sredy, posevnaia doza, temperatura kul'tivirovaniia. Dlia sovershenstvovaniia vektora ékspressii CASA byli sozdany dopolnitel'nye konstruktsii dlia produktsii varianta CASA s signal'noĭ posledovatel'nost'iu L-asparaginazy Erwinia carotovora (ansCASA) i “bezlidernogo” varianta CASA. Udalenie N-kontsevoĭ signal'noĭ posledovatel'nosti na poriadok snizhalo uroven' produktsii funktsional'no aktivnoĭ CASA i podavlialo rost shtamma. Vvedenie signal'noĭ posledovatel'nosti L-asparaginazy povyshalo udel'nuiu aktivnost' fermenta v poluchennom shtamme.
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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
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
