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A8398

7-Aminodesacetoxycephalosporanic acid

Name: 7-Aminodesacetoxycephalosporanic acid
Brand: SIGMA

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

NACRES:

NA.85

PubChem Substance ID:

24891339

UNSPSC Code:

51102829

EC Number:

244-870-1

MDL number:

MFCD09750368

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Properties

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

Description

General description

Chemical structure: β-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 .

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Hazard Classifications

Aquatic Chronic 3

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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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)

Altering the substrate specificity of cephalosporin acylase by directed evolution of the Beta -subunit.

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

[Hydrolase from Xanthomonas rubrilineans for synthesis of cefalexin].

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

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Global Trade Item Number

SKU	GTIN
A8398-5G	04061833391549
A8398-1G	04061833391525
A8398-250MG	04061833391532