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A8398

Sigma-Aldrich

7-Aminodesacetoxycephalosporanic acid

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Synonym(s):
7-ADCA
Empirical Formula (Hill Notation):
C8H10N2O3S
CAS Number:
22252-43-3
Molecular Weight:
214.24
EC Number:
244-870-1
MDL number:
MFCD09750368
UNSPSC Code:
51101500
PubChem Substance ID:
24891339
NACRES:
NA.85

form

powder or crystals

Quality Level

200

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

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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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
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.
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
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
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
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