Zwitterions

organic compound containing both amino and acidic functional groups, important in biology

Tetrodotoxin (TTX) is a potent neurotoxin. Its name derives from Tetraodontiformes, an order that includes pufferfish, porcupinefish, ocean sunfish, and triggerfish; several of these species carry the toxin. Although tetrodotoxin was discovered in these fish, it is found in several other animals (e.g., in blue-ringed octopuses, rough-skinned newts, and moon snails). It is also produced by certain infectious or symbiotic bacteria like Pseudoalteromonas, Pseudomonas, and Vibrio as well as other species found in symbiotic relationships with animals and plants.

In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion is a molecule that contains an equal number of positively and negatively charged functional groups. (1,2-dipolar compounds, such as ylides, are sometimes excluded from the definition.)

Ceftazidime, sold under the brand name Fortaz among others, is a third-generation cephalosporin antibiotic useful for the treatment of a number of bacterial infections. Specifically it is used for joint infections, meningitis, pneumonia, sepsis, urinary tract infections, malignant otitis externa, Pseudomonas aeruginosa infection, and vibrio infection. It is given by injection into a vein, muscle, or eye.

Trimethylglycine is an amino acid derivative with the formula . A colorless, water-soluble solid, it occurs in plants. Trimethylglycine is a zwitterion: the molecule contains both a quaternary ammonium group and a carboxylate group. Trimethylglycine was the first betaine discovered; originally it was simply called betaine because it was discovered in sugar beets (Beta vulgaris subsp. vulgaris). Several other betaines are now known.

thumb|400x400px|Cocamidopropyl betaine is an example of a betaine

Trigonelline is an alkaloid with chemical formula . It is a zwitterion formed by the methylation of the nitrogen atom of niacin (vitamin B3). Trigonelline is a product of niacin metabolism that is excreted in the urine of mammals.

chemical compound

Dimethylsulfoniopropionate (DMSP), is an organosulfur compound with the formula (CH3)2S+CH2CH2COO−. This zwitterionic metabolite can be found in marine phytoplankton, seaweeds, and some species of terrestrial and aquatic vascular plants. It functions as an osmolyte as well as several other physiological and environmental roles have also been identified. DMSP was first identified in the marine red alga Polysiphonia fastigiata.

Baeocystin, also known as norpsilocybin or '4-phosphoryloxy-N-methyltryptamine (4-PO-NMT'), is a zwitterionic alkaloid of the tryptamine family and an analogue of psilocybin (4-PO-DMT). It is found as a minor compound in most psilocybin mushrooms together with psilocybin, psilocin (4-HO-DMT), norbaeocystin (4-PO-T), and aeruginascin (4-PO-TMT). The compound is the N-demethylated derivative of psilocybin and the 4-phosphorylated derivative of norpsilocin (4-HO-NMT).

Tricine is an organic compound that is used in buffer solutions. The name tricine comes from tris and glycine, from which it was derived. It is a white crystalline powder that is moderately soluble in water. It is a zwitterionic amino acid that has a pKa1 value of 2.3 at 25 °C, while its pKa2 at 20 °C is 8.15. Its useful buffering range of pH is 7.4-8.8. Along with bicine, it is one of Good's buffering agents. Good first prepared tricine to buffer chloroplast reactions.

Arsenobetaine is an organoarsenic compound found in fish. It is the arsenic analog of trimethylglycine, commonly known as betaine. The biochemistry and biosynthesis of this molecule are similar to those of choline and glycine betaine.

Bicine is an organic compound used as a buffering agent. It is one of Good's buffers and has a pKa of 8.35 at 20 °C. It is prepared by the reaction of glycine with ethylene oxide, followed by hydrolysis of the resultant lactone.

chemical compound

Cephaloridine (or cefaloridine) is a first-generation semisynthetic derivative of antibiotic cephalosporin C. It is a Beta lactam antibiotic, like penicillin. Its chemical structure contains cephems,carboxyl groups and a pyridinium ring.

Diphthamide is a post-translationally modified histidine amino acid found in archaeal and eukaryotic elongation factor 2 (eEF-2).

Phosphocholine is an intermediate in the synthesis of phosphatidylcholine in tissues. Phosphocholine is made in a reaction, catalyzed by choline kinase, that converts ATP and choline into phosphocholine and ADP. Phosphocholine is a molecule found, for example, in lecithin.

Gaboxadol, also known as 4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3-ol (THIP) and by its former developmental code names Lu-2-030, MK-0928, and OV101, is a GABAA receptor agonist related to muscimol which was investigated for the treatment of insomnia and other conditions like Angelman syndrome but was never marketed. At lower doses, the drug has sedative and hypnotic effects, and at higher doses, it produces hallucinogenic effects. It is taken orally.

Cylindrospermopsin (abbreviated to CYN, or CYL) is a cyanotoxin produced by a variety of freshwater cyanobacteria. CYN is a polycyclic uracil derivative containing guanidino and sulfate groups. It is also zwitterionic, making it highly water soluble. CYN is toxic to liver and kidney tissue and is thought to inhibit protein synthesis and to covalently modify DNA and/or RNA. It is not known whether cylindrospermopsin is a carcinogen, but it appears to have no tumour-initiating activity in mice.

Perifosine (also KRX-0401) is a former drug candidate that was under development for a variety of cancer indications. It is an alkyl-phospholipid structurally related to miltefosine. Perifosine interrupts the PI3K/AKT/mTOR pathway by acting as an allosteric AKT inhibitor targeting the pleckstrin homology domain of AKT. It was being developed by Keryx Biopharmaceuticals who had licensed it from Æterna Zentaris Inc.

Bufothionine is a sulfur-containing compound which is present in the bufotoxins secreted by the parotoid gland of certain toads of the genera Bufo and Chaunus. The structure has been shown by X-ray crystallography to be (1,3,4,5-tetrahydro-5,5-dimethylpyrrolo-[4,3,2-de]quinolinio)-6-sulfate. This specific compound can be found in the skin of certain species of toad such as the Asiatic Toad, Chaunus arunco, Chaunus crucifer, Chaunus spinulosus, and Chaunus arenarum.

class of compounds

chemical compound

Edelfosine (ET-18-O-CH3; 1-octadecyl-2-O-methyl-glycero-3-phosphocholine) is a synthetic alkyl-lysophospholipid (ALP). It has antineoplastic (anti-cancer) effects.

class of chemical compounds

3-Dehydrocarnitine is an aliphatic quaternary ammonium betaine that is part of the carnitine family. At physiological pH of 7.3, the major species of 3-dehydrocarnitine is its zwitterionic form, the conjugate base of 3-dehydrocarnitinium. 3-Dehydrocarnitine is classified as a short-chain keto acid, as it has a carbon chain containing less than six carbon atoms. It is an intermediate in carnitine degradation and is formed from D- or L-carnitine. The enzymes responsible for the degradation of carnitine to 3-dehydrocarnitine are carnitine-3-dehydrogenase or (S)-carnitine-3-dehydrogenase.