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:
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: 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 .
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
P Travascio et al.
Biotechnology and bioengineering, 79(3), 334-346 (2002-07-13)
A new hydrophobic and catalytic membrane was prepared by immobilizing Penicillin G acylase (PGA, EC.3.5.1.11) from E. coli on a nylon membrane, chemically grafted with butylmethacrylate (BMA). Hexamethylenediamine (HMDA) and glutaraldehyde (Glu) were used as a spacer and coupling agent
C G Schroën et al.
Biotechnology and bioengineering, 73(3), 171-178 (2001-03-21)
During enzymatic kinetic synthesis of cephalexin, an activated phenylglycine derivative (phenylglycine amide or phenylglycine methyl ester) is coupled to the nucleus 7-aminodeacetoxycephalosporanic acid (7-ADCA). Simultaneously, hydrolysis of phenylglycine amide and hydrolysis of cephalexin take place. This results in a temporary
J Robin et al.
Biotechnology and bioengineering, 83(3), 361-368 (2003-06-05)
The growth stoichiometry of a Penicillium chrysogenum strain expressing the expandase gene from Streptomyces clavuligerus was determined in glucose-limited chemostat cultivations using a chemically defined medium. This strain produces adipoyl-7-aminodeacetoxycephalosporanic acid (ad-7-ADCA) when it is fed with adipic acid. The
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| A8398-5G | 04061833391549 |
| A8398-1G | 04061833391525 |
| A8398-250MG | 04061833391532 |
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