Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H12N2O5S |
| Molecular Weight | 272.278 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2N)C(O)=O
InChI
InChIKey=HSHGZXNAXBPPDL-HZGVNTEJSA-N
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
7-aminocephalosporanicacid (7-ACA) is convenient starting material for the industrial production of various kinds of semisynthetic cephalosporin antibiotics. In many cases, chemical modifications at the C-7 position is required. Industrially, 7-ACA is derived by chemical or enzymatic deacylation from cephalosporin C, which is fermentatively produced by Acremonium chrysogenum. 7-ACA is a stable only at neutral pHs, enzymatic manipulations are desirable for chemical modifications in the production of cephalosporin related compounds.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Thoughts on explaining cigarette smoking]. | 1987 Feb |
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| Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity. | 1992 |
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| A rapid and specific method to screen environmental microorganisms for cephalosporin acylase activity. | 2003 Jul |
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| Multivariate analysis and classification of the chemical quality of 7-aminocephalosporanic acid using near-infrared reflectance spectroscopy. | 2003 Jul 15 |
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| The kinetic properties of the carboxy terminal domain of the Bacillus licheniformis 749/I BlaR penicillin-receptor shed a new light on the derepression of beta-lactamase synthesis. | 2003 Jun |
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| An alternative procedure for preparation of cefdinir. | 2003 Jun |
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| An improved method for preparation of cefpodoxime proxetil. | 2003 May |
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| Deacylation activity of cephalosporin acylase to cephalosporin C is improved by changing the side-chain conformations of active-site residues. | 2003 Oct 10 |
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| Industrial enzymatic production of cephalosporin-based beta-lactams. | 2004 |
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| Synthesis and preliminary antimicrobial evaluation of new 7-(N-pyrrolyl) derivatives of cephalosporins. | 2004 |
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| Occupational asthma and IgE sensitization to 7-aminocephalosporanic acid. | 2004 Apr |
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| Batch production of deacetyl 7-aminocephalosporanic acid by immobilized cephalosporin-C deacetylase. | 2004 Aug |
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| Affinity labeled glutaryl-7-amino cephalosporanic acid acylase C130 can hydrolyze the inhibitor during crystallization. | 2004 Jan 16 |
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| [Compared D-amino acid oxidase expression in different Pichia pastoris host strains]. | 2004 Jul |
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| Construction and application of fusion proteins of D-amino acid oxidase and glutaryl-7-aminocephalosporanic acid acylase for direct bioconversion of cephalosporin C to 7-aminocephalosporanic acid. | 2004 Jun |
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| Modifying the substrate specificity of penicillin G acylase to cephalosporin acylase by mutating active-site residues. | 2004 Jun 25 |
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| Catalytic properties of D-amino acid oxidase in cephalosporin C bioconversion: a comparison between proteins from different sources. | 2004 Mar-Apr |
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| Toward the development of a cephalosporin-based dual-release prodrug for use in ADEPT. | 2004 Nov 12 |
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| Evolution of an acylase active on cephalosporin C. | 2005 Dec |
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| D-Amino acid oxidase: structure, catalytic mechanism, and practical application. | 2005 Jan |
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| Single-step conversion of cephalosporin-C to 7-aminocephalosporanic acid by free and immobilized cells of Pseudomonas diminuta. | 2005 Jul |
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| Reactions of pyrazolylborate-zinc-hydroxide complexes related to beta-lactamase activity. | 2005 Jun 13 |
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| 1H and 13 C spectral assignments of 7beta-(cinnamoyl-substituted)amino-3-acetoxymethyl-cephalosporins. | 2005 Mar |
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| Purification and characterization of a novel aminoacylase from Streptomyces mobaraensis. | 2005 Oct |
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| Enzymatic modifications of cephalosporins by cephalosporin acylase and other enzymes. | 2006 Apr-Jun |
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| Thermal inactivation of D-amino acid oxidase from Trigonopsis variabilis occurs via three parallel paths of irreversible denaturation. | 2006 Jul 5 |
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| Spectrophotometric assay for quantitative determination of 7-aminocephalosporanic acid from direct hydrolysis of cephalosporin C. | 2006 Mar 15 |
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| [Microspeciation of amphoteric molecules of unusual acid-base properties]. | 2007 |
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| Microbial production of 7-amino-cephalosporanic acid and new generation cephalosporins (cephalothin) by different processing strategies. | 2007 |
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| Reusability of entrapped cells of Pseudomonas diminuta for production of 7-aminocephalosporanic acid. | 2007 Apr |
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| Enzymatic synthesis of cephalosporins. The immobilized acylase from Arthrobacter viscosus: a new useful biocatalyst. | 2007 Dec |
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| Construction of recombinant Escherichia coli D11/pMSTO and its use in enzymatic preparation of 7-aminocephalosporanic acid in one pot. | 2007 May 1 |
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| [7-aminocephalosporanic acid induced bronchial asthma in two patients]. | 2007 Oct |
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| A colorimetric assay for the determination of acetyl xylan esterase or cephalosporin C acetyl esterase activities using 7-amino cephalosporanic acid, cephalosporin C, or acetylated xylan as substrate. | 2007 Oct 15 |
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| Site-specific protonation microequilibria of penicillin and cephalosporin beta-lactam core molecules. | 2007 Sep |
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| New active site oriented glyoxyl-agarose derivatives of Escherichia coli penicillin G acylase. | 2007 Sep 10 |
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| YesT: a new rhamnogalacturonan acetyl esterase from Bacillus subtilis. | 2008 Apr |
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| Properties and applications of microbial D-amino acid oxidases: current state and perspectives. | 2008 Feb |
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| Development of the semi-synthetic penicillins and cephalosporins. | 2008 Mar |
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| Optimization of glutaryl-7-aminocephalosporanic acid acylase expression in E. coli. | 2008 Oct |
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| The stabilizing effects of immobilization in D-amino acid oxidase from Trigonopsis variabilis. | 2008 Sep 17 |
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| Stepwise engineering of a Pichia pastoris D-amino acid oxidase whole cell catalyst. | 2010 Apr 26 |
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| Enhancement of glutaryl-7-aminocephalosporanic acid acylase activity of gamma-glutamyltranspeptidase of Bacillus subtilis. | 2010 Aug |
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| Occupational asthma in Korea. | 2010 Dec |
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| Environmentally safe production of 7-ACA by recombinant Acremonium chrysogenum. | 2010 Dec |
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| A single Phe54Tyr substitution improves the catalytic activity and thermostability of Trigonopsis variabilis D-amino acid oxidase. | 2010 Feb 28 |
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| Improved cross-linked enzyme aggregates for the production of desacetyl beta-lactam antibiotics intermediates. | 2010 Jan |
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| Protein engineering of penicillin acylase. | 2010 Jul |
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| Biosynthesis of cephalosporin-C acylase enzyme: optimal media design, purification, and characterization. | 2010 Oct |
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| Gene expressions changes in bronchial epithelial cells: markers for respiratory sensitizers and exploration of the NRF2 pathway. | 2014 Mar |
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9XI67897RG
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213-485-0
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2255
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m1699
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441328
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957-68-6
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C030735
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7-ACA
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DTXSID9045342
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SUBSTANCE RECORD
