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
NACRES:
NA.85
PubChem Substance ID:
UNSPSC Code:
51102829
EC Number:
244-870-1
MDL number:
InChI key
NVIAYEIXYQCDAN-CLZZGJSISA-N
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
SMILES string
CC1=C(N2[C@H](SC1)[C@H](N)C2=O)C(O)=O
form
powder or crystals
antibiotic activity spectrum
Gram-positive bacteria
mode of action
cell wall synthesis | interferes
storage temp.
2-8°C
Quality Level
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Related Categories
General description
Chemical structure: β-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.
hcodes
pcodes
Hazard Classifications
Aquatic Chronic 3
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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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
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)
R Saravanane et al.
Environmental technology, 30(10), 1016-1022 (2009-11-06)
The viability of treating high-concentration antibiotic wastewater by an anaerobic membrane bioreactor was studied using submerged flat sheet membrane. The objective of the study was to determine the effect of organic loading rate and hydraulic retention time on the removal
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.
Wynand B L Alkema et al.
European journal of biochemistry, 270(18), 3675-3683 (2003-09-03)
Penicillin acylase catalyses the hydrolysis and synthesis of semisynthetic beta-lactam antibiotics via formation of a covalent acyl-enzyme intermediate. The kinetic and mechanistic aspects of these reactions were studied. Stopped-flow experiments with the penicillin and ampicillin analogues 2-nitro-5-phenylacetoxy-benzoic acid (NIPAOB) and
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