Biomaterial Database

Synthesis of tritium-labelled isopenicillin N, penicillin N and 6-aminopenicillanic acid. 1975

J J Usher, and B Loder, and E P Abraham

1. Phenoxymethylpenicillin sulphoxide 4-methoxybenzyl ester was labelled with 3H in its 2-beta-methyl group. Its specific radioactivity was 362 mCi/mmol. 2. Removal of the side chain of this compound yielded the corresponding ester of 6-aminopenicillanic acid sulphoxide and coupling of the latter with the appropriate protected alpha-aminoadipic acid gave 4-methoxybenzyloxycarbonylisopenicillin N sulphoxide di-4-methoxybenzyl ester or the corresponding derivative of penicillin N. 3. Removal of the protective groups by hydrogenolysis and reduction of the sulphoxide group yielded 3H-labelled isopenicillin N or penicillin N. 4. 3H-labelled phenoxymethylpenicillin sulphoxide was obtained by hydrogenolysis from its 4-methoxybenzyl ester. Reduction of its sulphoxide group and subsequent removal of the side chain gave 3H-labelled 6-aminopenicillanic acid.

UI	MeSH Term	Description	Entries
D007553	Isotope Labeling	Techniques for labeling a substance with a stable or radioactive isotope. It is not used for articles involving labeled substances unless the methods of labeling are substantively discussed. Tracers that may be labeled include chemical substances, cells, or microorganisms.	Isotope Labeling, Stable,Isotope-Coded Affinity Tagging,Isotopically-Coded Affinity Tagging,Affinity Tagging, Isotope-Coded,Affinity Tagging, Isotopically-Coded,Isotope Coded Affinity Tagging,Labeling, Isotope,Labeling, Stable Isotope,Stable Isotope Labeling,Tagging, Isotope-Coded Affinity,Tagging, Isotopically-Coded Affinity
D010397	Penicillanic Acid	A building block of penicillin, devoid of significant antibacterial activity. (From Merck Index, 11th ed)	Acid, Penicillanic
D010404	Penicillin V	A broad-spectrum penicillin antibiotic used orally in the treatment of mild to moderate infections by susceptible gram-positive organisms.	Penicillin, Phenoxymethyl,Apocillin,Beromycin,Beromycin, Penicillin,Berromycin, Penicillin,Betapen,Fenoxymethylpenicillin,Pen VK,Penicillin V Potassium,Penicillin V Sodium,Penicillin VK,Phenoxymethylpenicillin,V-Cillin K,Vegacillin,Penicillin Beromycin,Penicillin Berromycin,Phenoxymethyl Penicillin,Potassium, Penicillin V,Sodium, Penicillin V,V Cillin K,V Sodium, Penicillin,VCillin K
D010406	Penicillins	A group of antibiotics that contain 6-aminopenicillanic acid with a side chain attached to the 6-amino group. The penicillin nucleus is the chief structural requirement for biological activity. The side-chain structure determines many of the antibacterial and pharmacological characteristics. (Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p1065)	Antibiotics, Penicillin,Penicillin,Penicillin Antibiotics
D002854	Chromatography, Paper	An analytical technique for resolution of a chemical mixture into its component compounds. Compounds are separated on an adsorbent paper (stationary phase) by their varied degree of solubility/mobility in the eluting solvent (mobile phase).	Paper Chromatography,Chromatographies, Paper,Paper Chromatographies
D002855	Chromatography, Thin Layer	Chromatography on thin layers of adsorbents rather than in columns. The adsorbent can be alumina, silica gel, silicates, charcoals, or cellulose. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	Chromatography, Thin-Layer,Thin Layer Chromatography,Chromatographies, Thin Layer,Chromatographies, Thin-Layer,Thin Layer Chromatographies,Thin-Layer Chromatographies,Thin-Layer Chromatography
D004586	Electrophoresis	An electrochemical process in which macromolecules or colloidal particles with a net electric charge migrate in a solution under the influence of an electric current.	Electrophoreses
D012588	Scintillation Counting	Detection and counting of scintillations produced in a fluorescent material by ionizing radiation.	Scintillation Counters,Counter, Scintillation,Counters, Scintillation,Counting, Scintillation,Scintillation Counter
D014316	Tritium	The radioactive isotope of hydrogen also known as hydrogen-3. It contains two NEUTRONS and one PROTON in its nucleus and decays to produce low energy BETA PARTICLES.	Hydrogen-3,Hydrogen 3
D015074	2-Aminoadipic Acid	A metabolite in the principal biochemical pathway of lysine. It antagonizes neuroexcitatory activity modulated by the glutamate receptor, N-METHYL-D-ASPARTATE; (NMDA).	alpha-Aminoadipic Acid,2 Aminoadipic Acid,2-Aminohexanedioic Acid,2 Aminohexanedioic Acid,Acid, 2 Aminoadipic,Acid, 2-Aminoadipic,Acid, 2-Aminohexanedioic,Acid, alpha-Aminoadipic,Aminoadipic Acid, 2,alpha Aminoadipic Acid