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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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
F Cui et al.
Wei sheng wu xue bao = Acta microbiologica Sinica, 38(4), 300-303 (2003-01-29)
Cephradine was synthesized by gamma-alumina-immobilized form of the penicillin G acylase of Bacillus megaterium with D-phenyglycine methylester hydrochloride (CH DGME.HCl) as acyl donor and 7-aminodeacetoxycephalosporanic acid (7-ADCA) as acyl acceptor. 0.1 g of 7-ADCA was dissolved by adding 2.5 ml
Maxim I Youshko et al.
Biotechnology and bioengineering, 85(3), 323-329 (2004-01-30)
Advantages of performing penicillin acylase-catalyzed synthesis of new penicillins and cephalosporins by enzymatic acyl transfer to the beta-lactam antibiotic nuclei in the supersaturated solutions of substrates have been demonstrated. It has been shown that the effective nucleophile reactivity of 6-aminopenicillanic
Ye-Wang Zhang et al.
Preparative biochemistry & biotechnology, 38(2), 129-138 (2008-03-06)
Enzymatic syntheses of cefaclor by immobilized penicillin acylase under kinetic control were carried out. According to the initial reaction rate ratio of synthesis to hydrolysis (Vs/Vh), penicillin acylase from Alcaligenes faecalis was chosen as the suitable catalyst for the synthesis
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