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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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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
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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