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Merck

68186

Sigma-Aldrich

Benzyl-penicilloinsäure Dinatriumsalz, Epimerenmischung

≥95% (HPLC)

Synonym(e):

4-Carboxy-5,5-dimethyl-α-[(2-phenylacetyl)-amino]-2-thiazolidinessigsäure Dinatriumsalz, Penicilloic acid Dinatriumsalz

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About This Item

Empirische Formel (Hill-System):
C16H18N2Na2O5S
CAS-Nummer:
Molekulargewicht:
396.37
UNSPSC-Code:
12352106
NACRES:
NA.85

Qualitätsniveau

Assay

≥95% (HPLC)

Methode(n)

HPLC: suitable
gas chromatography (GC): suitable

Farbe

white

Wirkungsspektrum von Antibiotika

Gram-negative bacteria
Gram-positive bacteria

Format

neat

Wirkungsweise

cell wall synthesis | interferes
enzyme | inhibits

Lagertemp.

2-8°C

InChI

1S/C16H20N2O5S/c1-16(2)12(15(22)23)18-13(24-16)11(14(20)21)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-13,18H,8H2,1-2H3,(H,17,19)(H,20,21)(H,22,23)

InChIKey

HCYWNSXLUZRKJX-UHFFFAOYSA-N

Allgemeine Beschreibung

This product is a penicilloic acid with the N-acyl group phenylacetyl as side-chain. In alkaline medium, 5R,6R-Benzylpenicilloic acid epimerizes slowly to 5S,6R-benzylpenicilloic acid until equilibrium.

Anwendung

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Sonstige Hinweise

Keep container tightly closed in a dry and well-ventilated place. Store under inert gas. Keep in a dry place.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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In der Dokumentenbibliothek finden Sie die Dokumentation zu den Produkten, die Sie kürzlich erworben haben.

Die Dokumentenbibliothek aufrufen

Chuangji Liu et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 879(7-8), 533-540 (2011-02-09)
A rapid, sensitive, and specific method for the determination of amoxicillin (AMO), amoxicilloic acid (AMA), amoxicillin diketopiperazine-2',5'-dione (DIKETO), penicillin G (PEN G), benzylpenicilloic acid (BPA-1), benzylpenilloic acid (BPA-2), and benzylpenillic acid (BPA-3) in bovine milk using ultra-high-performance liquid chromatography-tandem mass
I Ghebre-Sellassie et al.
Journal of pharmaceutical sciences, 73(1), 125-128 (1984-01-01)
5R,6R-Benzylpenicilloic acid was found to epimerize slowly in alkaline media to 5S,6R-benzylpenicilloic acid until equilibrium was established. Epimerization proceeded via the imine tautomer of penamaldic acid rather than the enamine form and was found to favor the 5S,6R-epimer at equilibrium.
Degradation of benzylpenicillin at pH 7.5 to D-benzylpenicilloic acid.
B B LEVINE
Nature, 187, 939-940 (1960-09-10)
Reza M Seifar et al.
Journal of chromatography. A, 1187(1-2), 103-110 (2008-02-26)
A rapid, sensitive and selective ion-pair reversed-phase liquid chromatography-electrospray ionization isotope dilution tandem mass spectrometry (IP-LC-ESI-ID-MS/MS) was developed for quantitative analysis of free intracellular metabolites in cell cultures. As an application a group of compounds involved in penicillin biosynthesis pathway
Sander S van Berkel et al.
ACS chemical biology, 8(10), 2112-2116 (2013-08-01)
β-Lactam antibiotics react with penicillin binding proteins (PBPs) to form relatively stable acyl-enzyme complexes. We describe structures derived from the reaction of piperacillin with PBP3 (Pseudomonas aeruginosa) including not only the anticipated acyl-enzyme complex but also an unprecedented complex with

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