A8398
7-Aminodesacetoxycephalosporanic acid
Synonym(s):
7-ADCA
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About This Item
Empirical Formula (Hill Notation):
C8H10N2O3S
CAS Number:
Molecular Weight:
214.24
EC Number:
MDL number:
UNSPSC Code:
51102829
PubChem Substance ID:
NACRES:
NA.85
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form
powder or crystals
Quality Level
antibiotic activity spectrum
Gram-positive bacteria
Mode of action
cell wall synthesis | interferes
storage temp.
2-8°C
SMILES string
CC1=C(N2[C@H](SC1)[C@H](N)C2=O)C(O)=O
InChI
1S/C8H10N2O3S/c1-3-2-14-7-4(9)6(11)10(7)5(3)8(12)13/h4,7H,2,9H2,1H3,(H,12,13)/t4-,7-/m1/s1
InChI key
NVIAYEIXYQCDAN-CLZZGJSISA-N
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General description
Chemical structure: ß-lactam
Application
7-Aminodesacetoxycephalosporanic acid is used in the synthesis of cephalosporins and for bioconversion studies .
Biochem/physiol Actions
7-ADCA is produced from penicillin G made by Penicillium chrysogenum involving several polluting chemical steps followed by enzymatic deacylation using penicillin acylase .
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Other Notes
Keep container tightly closed in a dry and well-ventilated place.
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Chronic 3
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Mutational analysis of a key residue in the substrate specificity of a cephalosporin acylase.
Linda G. Otten, Charles F. Sio, et al.
Chembiochem, 6, 820-825 (2004)
Linda G Otten et al.
The Journal of biological chemistry, 277(44), 42121-42127 (2002-08-29)
Using directed evolution, we have selected an adipyl acylase enzyme that can be used for a one-step bioconversion of adipyl-7-aminodesacetoxycephalosporanic acid (adipyl-7-ADCA) to 7-ADCA, an important compound for the synthesis of semisynthetic cephalosporins. The starting point for the directed evolution
A N Ivankin et al.
Prikladnaia biokhimiia i mikrobiologiia, 36(3), 303-306 (2000-06-27)
The use of peptide hydrolase (EC 3.4.13.1) from Xanthomonas rubrilineans for synthesis of the antibiotic cephalexin from 7-aminodesacetoxycephalosporanic acid was studied. The optimum conditions for production of cephalexin were determined, and the yield exceeded 80%. A method for monitoring the
C G P H Schroën et al.
Biotechnology and bioengineering, 80(2), 144-155 (2002-09-05)
Integrated process concepts for enzymatic cephalexin synthesis were investigated by our group, and this article focuses on the integration of reactions and product removal during the reactions. The last step in cephalexin production is the enzymatic kinetic coupling of activated
C G Schroën et al.
Biotechnology and bioengineering, 70(6), 654-661 (2000-11-07)
One of the building blocks of cephalosporin antibiotics is 7-amino-deacetoxycephalosporanic acid (7-ADCA). It is currently produced from penicillin G using an elaborate chemical ring-expansion step followed by an enzyme-catalyzed hydrolysis. However, 7-ADCA-like components can also be produced by direct fermentation.
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