19379-33-0

Basic information

• Product Name: L-Ampicillin
• Synonyms: 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-, L- (8CI);4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, [2S-[2α,5α,6β(R*)]]-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2S)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-;L-(+)-Ampicillin;L-Ampicillin
• CAS NO: 19379-33-0
• Molecular Formula: C₁₆H₁₉N₃O₄S
• Molecular Weight: 349.40476
• Mol File: 19379-33-0.mol

Chemical Properties

• Boiling Point: 683.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.45±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Aqueous Acid (Slightly), Aqueous Base (Slightly), DMSO (Slightly, Heated, Sonica
• PKA: 2.44±0.50(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: L-Ampicillin(CAS DataBase Reference)
• NIST Chemistry Reference: L-Ampicillin(19379-33-0)
• EPA Substance Registry System: L-Ampicillin(19379-33-0)

Safety Data

• Hazardous Substances Data: 19379-33-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-Ampicillin is used as an antibiotic for treating bacterial infections. It interferes with cell wall synthesis in bacteria, effectively inhibiting their growth and proliferation. This application is particularly useful in combating a wide range of bacterial infections, making it a valuable asset in the healthcare sector.
Used in Research and Development:
L-Ampicillin is also used as a research tool in the development of new antibiotics and understanding the mechanisms of bacterial resistance. Its unique properties and interactions with biopolymers and macromolecules make it an important compound for studying the effects of β-lactam antibiotics on bacterial cell wall synthesis and the potential for developing new treatments to combat antibiotic-resistant strains.

Upstream product

• 3511-16-8 6-epi-hetacillin 
• 40439-01-8 hetacillin 
• 551-16-6 6-Aminopenicillanic Acid 
• 15028-40-7 DL-2-phenylglycine methyl ester hydrochloride 
• 15028-39-4 L-2-phenylglycine methyl ester hydrochloride 
• 2935-35-5 (S)-2-phenylglycine 
• 5491-18-9 (S)-N-(benzyloxycarbonyl)phenylglycine 
• 6591-61-3 D-(-)-α-aminophenylacetic acid methyl ester 
• 65587-54-4 2',2'-Dibrompropoxycarbonyl-ampicillin-ONa 

Downstream Products

• 94595-14-9 2-(3,6-dioxo-5-phenylpiperazine-2-yl)-5,5-dimethylthiazolidine-4-carboxylic acid 
• 82922-25-6 (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[2-phenyl-2-(2-phenyl-isoureido)-acetylamino]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 82922-24-5 C₃₀H₂₈N₅O₆S^(1-)*Na⁽¹⁺⁾ 
• 82922-26-7 (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[2-phenyl-2-(2-o-tolyl-isoureido)-acetylamino]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 82934-39-2 C₃₂H₃₂N₅O₆S^(1-)*Na⁽¹⁺⁾ 
• 96661-43-7 p-bromophenacyl-6-β-<(4-methyl-3-(4,4-dimethyloxazolin-2-yl)-1,4-dihydropyridylmethylcarbonylaminophenylacetyl)amino>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 96661-44-8 p-bromophenacyl-6-β-<(4-n-butyl-3-(4,4-dimethyloxazolin-2-yl)-1,4-dihydropyridylmethylcarbonylaminophenylacetyl)amino>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 96661-42-6 p-bromophenacyl-6-β-<(4-phenyl-3-(4,4-dimethyloxazolin-2-yl)-1,4-dihydropyridylmethylcarbonylaminophenylacetyl)amino>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 96661-46-0 6-β-<(4-methyl-3-(4,4-dimethyloxazolin-2-yl)-1,4-dihydropyridylmethylcarbonylaminophenylacetyl)amino>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid potassium salt 
• 96661-47-1 6-β-<(4-n-butyl-3-(4,4-dimethyloxazolin-2-yl)-1,4-dihydropyridylmethylcarbonylaminophenylacetyl)amino>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid potassium salt 
• 96661-45-9 6-β-<(4-phenyl-3-(4,4-dimethyloxazolin-2-yl)-1,4-dihydropyridylmethylcarbonylaminophenylacetyl)amino>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid potassium salt 
• 145236-53-9 (5R,6R)-3,3-Dimethyl-7-oxo-6-(3-oxo-4-phenyl-3H-[1,2,5]thiadiazol-2-yl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 51727-23-2 p-bromophenacyl-6-β-<(aminophenylacetyl)amino>-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 78570-12-4 2-hydroxy-3-phenyl-6-ethylpyrazine 

Relevant articles and documents

THERAPEUTIC USE OF LEVOROTATORY ?-LACTAMS IN HEMATOPOIESIS, IMMUNO-ONCOLOGY THERAPY, AND REGULATION OF LIPOPROTEIN AND APOLIPOPROTEIN LEVELS

A method for increasing the number of CD4+ T-lymphocytes in the serum of a subject in need of such treatment comprising administering to the subject a pharmaceutical composition comprising an amount of an L-isomer of β-lactam effective to increase the number of CD4+ T-lymphocytes in said patient's serum.

Amino ester hydrolase from Xanthomonas campestris pv. campestris, ATCC 33913 for enzymatic synthesis of ampicillin

α-Amino ester hydrolases (AEH) are a small class of proteins, which are highly specific for hydrolysis or synthesis of α-amino containing amides and esters including β-lactam antibiotics such as ampicillin, amoxicillin, and cephalexin. A BLAST search revealed the sequence of a putative glutaryl 7-aminocephalosporanic acid (GL-7-ACA) acylase 93% identical to a known AEH from Xanthomonas citri. The gene, termed gaa, was cloned from the genomic DNA of Xanthomonas campestris pv. campestris sp. strain ATCC 33913 and the corresponding protein was expressed into Escherichia coli. The purified protein was able to perform both hydrolysis and synthesis of a variety of α-amino β-lactam antibiotics including (R)-ampicillin and cephalexin, with optimal ampicillin hydrolytic activity at 25 °C and pH 6.8, with kinetic parameters of kcat of 72.5 s-1 and KM of 1.1 mM. The synthesis parameters α, βo, and γ for ampicillin, determined here first for this class of proteins, are α = 0.25, βo = 42.8 M-1, and γ = 0.23, and demonstrate the excellent synthetic potential of these enzymes. An extensive study of site-directed mutations around the binding pocket of X. campestris pv. campestris AEH strongly suggests that mutation of almost any first-shell amino acid residues around the active site leads to inactive enzyme, including Y82, Y175, D207, D208, W209, Y222, and E309, in addition to those residues forming the catalytic triad, S174, H340, and D307.

Chemical reactivity of penicillins and cephalosporins. Intramolecular involvement of the acyl-amido side chain

The rate of degradation of 6-epi-ampicillin in acidic, neutral, and alkaline aqueous solutions was followed at 35 °C and an ionic strength of 0.5 mol dm-3 (KCl) by high-performance liquid chromatography (HPLC) and spectrophotometric assays. Pseudo-first-order rate constants were determined in a variety of buffer solutions, and the overall pH-rate profile was obtained by extrapolation to zero buffer concentration. The hydrolysis of 6- epi-ampicillin is subject to acid and hydroxide-ion catalysis and, for a penicillin, an unusual pH-independent reaction. Intramolecular general base- catalyzed hydrolysis by the side chain amido group is proposed to explain the enhanced rate of neutral hydrolysis of 6-epi-ampicillin and cephalosporins. The β-lactam of 6-epi-ampicillin also undergoes intramolecular aminolysis by nucleophilic attack of the 6-α side chain amino group to give a stable piperazine-2,5-dione derivative. The low effective molarity for intramolecular aminolysis of only 40 M is partly attributed to the unfavorable trans to cis isomerization about the 6-amide side chain required for ring closure. Theoretical calculations show that the intramolecular aminolysis of 6-epi-ampicillin nucleophilic attack occurs from the α-face of the β-lactam ring with an activation energy of 14.4 kcal/mol.

Extremely Selective and Mild Cleavage of β-Haloalkyl Groups by Cobalt(I)phthalocyanine Anion in Semisyntheses of β-Lactam Antibiotics

Cleavage of β-haloalkyl groups can be performed extremely selectively by cobalt(I)phthalocyanine anion under very mild conditions, qualifying it best in the chemistry of highly sensitive β-lactam antibiotics.This is demonstrated in penicillin and cephalosporin semisyntheses.