Amino acid derivatives

Aspartame is an artificial, non-saccharide sweetener commonly used as a sugar substitute in foods and beverages. It is 200 times sweeter than sucrose, and is a methyl ester of the aspartic acid/phenylalanine dipeptide with brand names NutraSweet, Equal, and Canderel. Discovered in 1965, aspartame was approved by the US Food and Drug Administration (FDA) in 1974 and re-approved in 1981 after its initial approval was briefly revoked.

Acetylcysteine or '''N-acetylcysteine (NAC'; not to be confused with N''-acetylcarnosine, which is also abbreviated NAC) is a mucolytic that is used to treat paracetamol (acetaminophen) overdose and to loosen thick mucus in individuals with chronic bronchopulmonary disorders, such as pneumonia and bronchitis. It has been used to treat lactobezoar in infants. It can be taken intravenously, orally (swallowed by mouth), or inhaled as a mist by use of a nebulizer. It is also sometimes used as a dietary supplement.

Lisinopril is a medication belonging to the drug class of angiotensin-converting enzyme (ACE) inhibitors and is used to treat hypertension (high blood pressure), heart failure, and heart attacks. For high blood pressure it is usually a first-line treatment. It is also used to prevent kidney problems in people with diabetes mellitus. Lisinopril is taken orally (swallowed by mouth). Full effect may take up to four weeks to occur.

Valaciclovir, also spelled valacyclovir, is an antiviral medication used to treat outbreaks of herpes simplex or herpes zoster (shingles). It is also used to prevent cytomegalovirus following a kidney transplant in high risk cases. It is taken by mouth.

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.

Valganciclovir, sold under the brand name Valcyte among others, is an antiviral medication used to treat cytomegalovirus (CMV) infection in those with HIV/AIDS or following organ transplant. It is often used long term as it only suppresses rather than cures the infection. Valganciclovir is taken by mouth.

Prilocaine () is a local anesthetic of the amino amide type first prepared by Claes Tegner and Nils Löfgren. In its injectable form (trade name Citanest), it is often used in dentistry. It is also often combined with lidocaine as a topical preparation for dermal anesthesia (lidocaine/prilocaine or EMLA), for treatment of conditions like paresthesia. As it has low cardiac toxicity, it is commonly used for intravenous regional anaesthesia (IVRA).

an amino acid derivative that acts as a specific agonist at the NMDA receptor mimicking the action of glutamate

Carbocisteine, also called carbocysteine, is a mucolytic that reduces the viscosity of sputum and so can be used to help relieve the symptoms of chronic obstructive pulmonary disorder (COPD) and bronchiectasis by allowing the sufferer to bring up sputum more easily. Carbocisteine should not be used with antitussives (cough suppressants) or medicines that dry up bronchial secretions.

'''N-Formylmethionine''' (fMet, HCO-Met, For-Met) is a derivative of the amino acid methionine in which a formyl group has been added to the amino group. It is specifically used for initiation of protein synthesis from bacterial and organellar genes, and may be removed post-translationally.

'''S-Adenosyl-L-homocysteine (SAH') is the biosynthetic precursor to homocysteine. SAH is formed by the demethylation of S''-adenosyl-L-methionine. Adenosylhomocysteinase converts SAH into homocysteine and adenosine.

Lymecycline is a tetracycline broad-spectrum antibiotic. It is approximately 5,000 times more soluble than tetracycline base and is unique amongst tetracyclines in that it is absorbed by an active transport process across the intestinal wall, making use of the same fast and efficient mechanism by which carbohydrates are absorbed.

chemical compound

Cilastatin inhibits the human enzyme dehydropeptidase.

Glycocyamine (or guanidinoacetate) is a metabolite of glycine in which the amino group has been converted into a guanidine by guanylation (transfer of a guanidine group from arginine). In vertebrate organism it is then transformed into creatine by methylation.

chemical compound

pair of enantiomers

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.

Acetyl-L-carnitine (ALCAR or ALC), also known as levacecarnine, is an acetylated form of L-carnitine. It is naturally produced by the human body, and it is available as a dietary supplement. Acetylcarnitine is broken down in the blood by plasma esterases to carnitine which is used by the body to transport fatty acids into the mitochondria for breakdown and energy production.

Coprine is a mycotoxin. It was first isolated from common inkcap (Coprinopsis atramentaria). It occurs in mushrooms in the genus Coprinopsis, specifically within sections Alopeciae, Atramentariae, and Picaceae. When combined with alcohol, it causes "Coprinus syndrome". It inhibits the enzyme aldehyde dehydrogenase, which is involved in the metabolism of alcohol. This inhibition leads to a buildup of acetaldehyde, causing an alcohol flush reaction. Because of this, the mushroom is commonly referred to as '''Tippler's Bane.'''

chemical compound

chemical compound

'''N-Methylphenethylamine (NMPEA''') is a naturally occurring trace amine neuromodulator in humans that is derived from the trace amine, phenethylamine (PEA). It has been detected in human urine (<1&nbsp;μg over 24&nbsp;hours) and is produced by phenylethanolamine N-methyltransferase with phenethylamine as a substrate, which significantly increases PEA's effects. PEA breaks down into phenylacetaldehyde which is further broken down into phenylacetic acid by monoamine oxidase. When this is inhibited by monoamine oxidase inhibitors, it allows more of the PEA to remain present and produce psychoac

Isovaleramide is an organic compound with the formula (CH3)2CHCH2C(O)NH2. The amide derived from isovaleric acid, it is a colourless solid.

γ-L-Glutamyl-L-cysteine, also known as γ-glutamylcysteine (GGC), is a dipeptide found in animals, plants, fungi, some bacteria, and archaea. It has a relatively unusual γ-bond between the constituent amino acids, L-glutamic acid and L-cysteine and is a key intermediate in the γ-glutamyl cycle first described by Meister in the 1970s. It is the most immediate precursor to the antioxidant glutathione.

Tiopronin, sold under the brand name Thiola, is a medication used to control the rate of cystine precipitation and excretion in the disease cystinuria.

Agaritine is an aromatic hydrazine-derivative mycotoxin in mushroom species of the genus Agaricus. It is an α-aminoacid and a derivative of phenylhydrazine.

Opines are low molecular weight compounds found in plant crown gall tumors or hairy root tumors produced by pathogenic bacteria of the genus Agrobacterium and Rhizobium. Opine biosynthesis is catalyzed by specific enzymes encoded by genes contained in a small segment of DNA (known as the T-DNA, for 'transfer DNA'), which is part of the Ti plasmid (in Agrobacterium) or Ri plasmid (in Rhizobium), inserted by the bacterium into the plant genome. The opines are used by the bacterium as an important energy, carbon and nitrogen source. Each strain of Agrobacterium and Rhizobium induces and cataboliz

Oxaceprol is an anti-inflammatory drug used in the treatment of osteoarthritis. It is derived from L-proline, a DNA-encoded amino acid. The active effect of Oxaceprol is to inhibit the adhesion and migration of white blood cells.

Aceglutamide (brand name Neuramina), or aceglutamide aluminium (brand name Glumal), also known as acetylglutamine, is a psychostimulant, nootropic, and antiulcer agent that is marketed in Spain and Japan. It is an acetylated form of the amino acid L-glutamine, the precursor of glutamate in the body and brain. Aceglutamide functions as a prodrug to glutamine with improved potency and stability.

chemical compound

chemical compound

Octopine is a derivative of the amino acids arginine and alanine. It was the first member of the class of chemical compounds known as opines to be discovered. Octopine gets its name from Octopus octopodia from which it was first isolated in 1927.

'''N(6)-Carboxymethyllysine' (CML), also known as N''ε-(carboxymethyl)lysine, is an advanced glycation endproduct&nbsp;(AGE). CML has been the most used marker for AGEs in food analysis.

chemical compound

3-Methylhistidine (3-MH) is a post-translationally modified amino acid which is excreted in human urine. Urinary concentration of 3-methylhistidine is a biomarker for skeletal muscle protein breakdown in humans who have been subject to muscle injury. Urinary 3-methylhistidine concentrations are also elevated from consumption of soy-based products and meat, particularly chicken.

Polylysine refers to several types of lysine homopolymers, which may differ from each other in terms of stereochemistry (D/L; the L form is natural and usually assumed) and link position (α/ε). Of these types, only ε-poly-L-lysine is produced naturally.

Alanosine (also called SDX-102) is a substance that has been studied for the treatment of pancreatic cancer. It is an antimetabolite. It is used as one of a few experimental treatments for patients with deadly pancreatic cancer when the main chemotherapeutic treatment regimen of gemcitabine is no longer useful.

Nopaline is a chemical compound derived from the amino acids glutamic acid and arginine. It is classified as an opine. Ti plasmids are classified on the basis of the different types of opines they produce. These may be nopaline plasmids, octopine plasmids and agropine plasmids. These opines are condensation products of amino acids and keto acids or may be derived from sugars. The opines are used as carbon and nitrogen sources and metabolized by Agrobacterium.

chemical compound

Biocytin is a chemical compound that is an amide formed from the vitamin biotin and the amino acid L-lysine. As an intermediate in the metabolism of biotin, biocytin occurs naturally in blood serum and urine.

chemical compound

Acivicin is an analog of glutamine. It is an inhibitor of gamma-glutamyl transferase.

Fenclonine, also known as '''para-chlorophenylalanine (PCPA'''), acts as a selective and irreversible inhibitor of tryptophan hydroxylase, which is a rate-limiting enzyme in the biosynthesis of serotonin.

Stampidine is an experimental nucleoside reverse transcriptase inhibitor (NRTI) with anti-HIV activity.

chemical compound

Tabtoxin, also known as wildfire toxin, is a simple monobactam phytotoxin produced by Pseudomonas syringae. It is the precursor to the antibiotic tabtoxinine β-lactam (TBL). It is produced by: Pseudomonas syringae pv. tabaci, the causal agent of the wildfire of tobacco. P. syringae pv. coronafaciens P. syringae pv. garcae P. syringae BR2, causes a disease of bean (Phaseolus vulgaris) similar to tobacco wildfire. This organism is closely related to P. syringae pv. tabaci but cannot be classified in the pathovar tabaci because it is not pathogenic on tobacco.

group of stereoisomers

'(S)-3,5-Dihydroxyphenylglycine or DHPG' is a potent agonist of group I metabotropic glutamate receptors (mGluRs) mGluR1 and mGluR5.

Nitrosoproline is a nitroso derivative of the amino acid proline.

Acetyllysine (or acetylated lysine) is an acetyl-derivative of the amino acid lysine. There are multiple forms of acetyllysine: this article is about N-ε-acetyl-L-lysine; another form is N-α-acetyl-L-lysine.

Methylselenocysteine (Me-Sec), also known as '''Se-methylselenocysteine' (SeMSC), is an analog of S''-methylcysteine in which the sulfur atom is replaced with a selenium atom.

Citiolone is a drug used in liver therapy.

Aspartylglucosamine is a derivative of aspartic acid.

CPHPC ((R)-1-{6-[(R)-2-carboxypyrrolidin-1-yl]-6-oxohexanoyl}pyrrolidine-2-carboxylic acid) is a proline-derived small molecule able to strip amyloid P (AP) from deposits by reducing levels of circulating serum amyloid P (SAP). The SAP-amyloid association has also been identified as a possible drug target for anti-amyloid therapy, with the recent development and first stage clinical trials of CPHPC for amyloidosis.

chemical compound

Hadacidin, and hadacidin analogues, have anticancer activity and activity against adenylosuccinate synthetase.

Dibromotyrosine is an antithyroid preparation and a derivative of the natural amino acid tyrosine.

5-Iodowillardiine is a selective agonist for some kainate receptor subunits with only limited effects at AMPA receptors. It activates kainate receptors containing GluK1 (GluR5) or GluK5 (KA2) subunits, but it does not act on GluK2 (GluR6) subunits. It is an excitotoxic neurotoxin in vivo, but has proved highly useful for characterising the subtypes and function of the various kainate receptors in the brain and spinal cord.

Ombrabulin was an experimental drug candidate discovered by Ajinomoto and further developed by Sanofi-Aventis. Ombrabulin is a combretastatin A-4 derivative that exerts its antitumor effect by disrupting the formation of blood vessels needed for tumor growth.