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68186

Sigma-Aldrich

Benzylpenicilloic acid disodium salt, mixture of epimeres

≥95% (HPLC)

Synonym(s):

4-Carboxy-5,5-dimethyl-α-[(2-phenylacetyl)amino]-2-thiazolidineacetic acid disodium salt, Penicilloic acid disodium salt

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About This Item

Empirical Formula (Hill Notation):
C16H18N2Na2O5S
CAS Number:
13057-98-2
Molecular Weight:
396.37
UNSPSC Code:
12352106
NACRES:
NA.85

Quality Level

100

Assay

≥95% (HPLC)

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

color

white

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

format

neat

Mode of action

cell wall synthesis | interferes
enzyme | inhibits

storage temp.

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)

InChI key

HCYWNSXLUZRKJX-UHFFFAOYSA-N

General description

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.

Application

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

Other Notes

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCBM4914V
BCBM4914

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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
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
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
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)

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