7-Aminocephalosporanic acid
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| Category | Antibiotics |
| Catalog number | BBF-00674 |
| CAS | 957-68-6 |
| Molecular Weight | 272.28 |
| Molecular Formula | C10H12N2O5S |
| Purity | >98% |
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Description
It is the starting material for the semisynthesis of cephalosporin and can be prepared by mild acid hydrolysis or enzymatic hydrolysis of cephalosporin C.
Specification
| Synonyms | 7-ACA |
| Storage | 2-8°C |
| IUPAC Name | (6R,7R)-3-(acetyloxymethyl)-7-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)N)SC1)C(=O)O |
| InChI | InChI=1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)/t6-,9-/m1/s1 |
| InChI Key | HSHGZXNAXBPPDL-HZGVNTEJSA-N |
Properties
| Appearance | Colorless Crystal |
| Boiling Point | 560.6±50.0 °C (Predicted) |
| Melting Point | > 300 °C |
| Density | 1.467 g/cm3 (Predicted) |
Reference Reading
1.Process design and evaluation of production of bioethanol and β-lactam antibiotic from lignocellulosic biomass.
Kim SB1, Park C2, Kim SW3. Bioresour Technol. 2014 Nov;172:194-200. doi: 10.1016/j.biortech.2014.09.031. Epub 2014 Sep 16.
To design biorefinery processes producing bioethanol from lignocellulosic biomass with dilute acid pretreatment, biorefinery processes were simulated using the SuperPro Designer program. To improve the efficiency of biomass use and the economics of biorefinery, additional pretreatment processes were designed and evaluated, in which a combined process of dilute acid and aqueous ammonia pretreatments, and a process of waste media containing xylose were used, for the production of 7-aminocephalosporanic acid. Finally, the productivity and economics of the designed processes were compared.
2.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.
3.Immobilization and stabilization of cephalosporin C acylase on aminated support by crosslinking with glutaraldehyde and further modifying with aminated macromolecules.
He H1, Wei Y, Luo H, Li X, Wang X, Liang C, Chang Y, Yu H, Shen Z. Biotechnol Prog. 2015 Mar-Apr;31(2):387-95. doi: 10.1002/btpr.2044. Epub 2015 Feb 2.
In this work, cephalosporin C acylase (CA), a heterodimeric enzyme of industrial potential in direct hydrolysis of cephalosporin C (CPC) to 7-aminocephalosporanic acid (7-ACA), was covalently immobilized on the aminated support LX1000-HA (HA) with two different protocols. The stability of CA adsorbed onto the HA support followed by crosslinking with glutaraldehyde (HA-CA-glut) was better than that of the CA covalently immobilized on the glutaraldehyde preactivated HA support (HA-glut-CA). The thermostabilization factors (compared with the free enzyme) of these two immobilized enzymes were 11.2-fold and 2.2-fold, respectively. In order to improve the stability of HA-CA-glut, a novel strategy based on postimmobilization modifying with aminated molecules was developed to take advantage of the glutaraldehyde moieties left on the enzyme and support. The macromolecules, such as polyethyleneimine (PEI) and chitosan, had larger effects than small molecules on the thermal stability of the immobilized enzyme perhaps due to crosslinking of the enzymes and support with each other.
4.Characterization of cross-linked immobilized arylesterase from Gluconobacter oxydans 621H with activity toward cephalosporin C and 7-aminocephalosporanic acid.
Inmaculada NG1, Francisco GC1. Biotechnol Prog. 2016 Jan;32(1):36-42. doi: 10.1002/btpr.2178. Epub 2015 Oct 15.
Cross-linked enzyme aggregates (CLEAs) were prepared from several precipitant agents using glutaraldehyde as a cross-linking agent with and without BSA, finally choosing a 40% saturation of ammonium sulfate and 25 mM of glutaraldehyde. The CLEAs obtained under optimum conditions were biochemically characterized. The immobilized enzyme showed higher thermal activity and a broader range of pH and organic solvent tolerance than the free enzyme. Arylesterase from Gluconobacter oxydans showed activity toward cephalosporin C and 7-aminocephalosporanic acid. The CLEAs had a Kcat/KM of 0.9 M(-1) /S(-1) for 7-ACA (7-aminocephalosporanic acid) and 0.1 M(-1) /S(-1) for CPC (cephalosporin c), whereas free enzyme did not show a typical Michaelis-Menten kinetics. © 2015 American Institute of Chemical Engineers Biotechnol. Prog., 32:36-42, 2016.
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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 ╳
