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A8398

Sigma-Aldrich

7-Aminodesacetoxycephalosporanic acid

Synonym(s):

7-ADCA

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About This Item

Empirical Formula (Hill Notation):
C8H10N2O3S
CAS Number:
22252-43-3
Molecular Weight:
214.24
EC Number:
244-870-1
MDL number:
MFCD09750368
UNSPSC Code:
51102829
PubChem Substance ID:
24891339
NACRES:
NA.85

form

powder or crystals

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

H412

Precautionary Statements

P273 - P501

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

Certificates of Analysis (COA)

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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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