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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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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)
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
P Travascio et al.
Biotechnology progress, 18(5), 975-985 (2002-10-05)
The effect of methanol on the kinetically controlled synthesis of cephalexin by free and immobilized penicillin G acylase (PGA) was investigated. Catalytic and hydrophobic membranes were obtained by chemical grafting, activation, and PGA immobilization on hydrophobic nylon supports. Butyl methacrylate
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