Amino Acids (AA)

<p>Applications (4S)-4-Hydroxy-L-isoleucine is 4S isomer of 4-Hydroxyisoleucine, which is used as a treatment for type II diabetes.<br>References Martinez-Force, E., et al.: Biotechnol. Tech., 5, 209 (1991); Sauvaire, Y., et al.: Diabetes, 47, 206 (1998), Narender, T., et al.: Bioorg. Med. Chem. Lett., 2006, 16, 293 (2006);<br></p>

<p>Applications L-Serine-13C3 is the isotope labelled analog of L-Serine (S270995); a compound used in the synthesis of purines and pyrimidines as antibacterial/antifungal agents, as well as acting as a proteinogenic compound.<br>References Olivella, M. et al.: Bioorg. Med. Chem., 20, 6109 (2012)<br></p>

<p>Stability Very Hygroscopic<br>Applications 6-N-Trimethyl L-Lysine-d9, is the labeled analogue of Nε,Nε,Nε-Trimethyllysine, a metabolite and cofactor on the metabolic pathways.<br>References Rebouche C.J., et. al, J. Nutrition, 116(5), 751-759 (1986); Vaz, F.M et. al, J. Bio. Chem., 276(36), 33512-33517 (2001);<br></p>

<p>Stability Air Sensitive<br>Applications L-Homocysteine is the hydrolysis product of adenosine (A280400), a purine nucleoside. Metabolic fate of L-Homocysteine is converted back to L-Methionine( M260440) via tetrahydrofolate.<br>References Liu, X.D., et al.: Org. BIomolec. Chem., 11, 4258 (2013); Chen, C.S., et al.: Nueroendocrinol., 97, 232 (2013);<br></p>

<p>Applications Labelled L-Citrulline. An amino acid, first isolated from the juice of watermelon, Citrullus vulgaris Schrad., Cucurbitaceae. Used in the treatment of asthenia.<br>References Kurtz, et al.: J. Biol. Chem., 122, 477 (1938), Rajantie, J., et al.: J. Pediatr., 97, 927 (1980), Carpenter, T.O., et al.: N. Engl. J. Med., 312, 290 (1985),<br></p>

<p>Applications Suberylglycine is one of the acylglycines, an important class of metabolites that have been used in the diagnosis of several inborn errors of metabolism (IEM).<br>References Costa, C., et al.: J. Pharmaceut. Biomed. Anal., 21, 1215 (2000), Garcia-Villoria, J., et al.: Clin. Biochem., 42, 2 (2009), Scalbert, A., et al.: Metabolomics, 5, 435 (2009),<br></p>

<p>Applications N-Cinnamylglycine is a derivative of ferulic acid (F308900), a widely distributed compound in plants that is used as an antioxidant and food preservative.<br>References Jellum,E., et al.: J. Pharma. Biomed. Anal., 9, 663 (1991); Kayahara, H., et al.: Anticancer. Res., 19, 3763 (1999); Bollina, V., et al.: Plant. Molec. Biol., 77, 355 (2011);<br></p>

<p>Applications L-Glutamic Acid-d5 is an non-essential amino acid. Its salt form (glutamate) is an important neurotransmitter that plays a key role in long-term potentiation and is important for learning and memory. It is also a key molecule in cellular metabolism.<br>References McEntee, W., et al.: Psychopharmacology, 111, 391 (1993), Manev, H., et al.: Mol. Pharmacol., 36, 106 (1989)<br></p>

<p>Applications A cysteine derivative as potential antitumor agent. (A609645)A vitamin needed to synthesize DNA, conduct DNA repair and methylate DNA, it also acts as a cofactor in biological reactions involving folate. (F680300)<br>References Paul, B., et al.: J. Med. Chem., et al.: 19, 1002 (1976), Xu, L., et al.: Mol. Pharm., 7, 1311 (2010), Everette, J., et al.: J. Agric. Food Chem., 58, 8139 (2010), Alshatwi, A., et al.: Food, Chem., Toxicol., 48, 1881 (2010), McKay, D., et al.: Nut. J., 9 (2010),<br></p>

<p>Applications A metabolite of Acrylonitrile (ACN).<br>References Guengerich, F., et al.: Cancer Res., 41, 4925 (1981), Leonard, A., et al.: Mutation Res., 436, 263 (1999), Stadler, R., et al.: J. Agric. Food Chem., 52, 5550 (2004), Dybing, E., et al.: Food Chem. Toxicol., 43, 365 (2005), Rice, J., et al.: Mutation Res., 580, 3 (2005),<br></p>

<p>Applications 2-Chloro-1-methylquinolinium tetrafluoroborate (cas# 16843-24-6) is a useful research chemical.<br></p>

<p>Applications 1-(2-Chloroethoxy)-2-methoxy benzene, is an impurity of Carvedilol (C184625), a nonselective β-adrenergic blocker with α1-blocking activity. Carvedilol is an antihypertensive used in the treatment of congestive heart failure.<br>References Hirohashi, M., et al.: Arzneim.-Forsch., 40, 735 (1990); Packer, M., et al.: N. Engl. J. Med., 334, 1349 (1996);<br></p>

<p>Applications N-Acetyl-L-cystine is an antioxidant, used in the treatment of influenza A virus pandemic (1). N-Acetyl-L-cystine promotes fertilization by reducing disulfide bonds in zona pellucida of mouse (2).Releases N-Acetyl-L-cysteine, which is an antidote for paracetamol poisoning.<br>References (1) Zhang, R., et al.: (2014) Int. Immunopharmacol. 22: 1-8 (2) Takeo, T., et al.: Biol Reprod. (2015) 92: 1-7<br></p>

<p>Applications 4-Aminobutyl-d8 Guanidine is the labelled analog of the decarboxylation product of the amino acid arginine (A769500) and also an intermediate in polyamine biosynthesis.<br>References Golding, B.T., et al.: Biochem. Soc. Trans., 22, 391S (1994);<br></p>

<p>Applications (+)-α-Methyl-β-alanine is a reactant for the chemoenzymatic assembly of cryptophycins as potent anticancer therapeutics.<br>References Magarvey, N.A., et al.: ACS Chem. Biol., 1, 766-779 (2006)<br></p>

<p>Applications A non-essential amino acid found in food sources and dietary supplements. Its conjugate base D-aspartate has potential use as a a therapeutic agent in the treatment of schizophrenia-related symptoms.<br>References Errico, F. et al.: J. Neurosci., 28, 10404 (2008); Denu, J.M. et al.: Biochem., 34, 3396 (1995); Chen, P.E. et al.: Mol. Pharmacol., 67, 1470 (2005);<br></p>

<p>Applications N-Isobutyrylglycine detection is a useful diagnostic tool in the diagnosis of many organic acidemias and mitochondrial fatty acid β-oxidation defects. N-Isobutyrylglycine detection is also used in the diagnosis of isobutyryl-CoA dehydrogenase deficiency.<br>References Costa, C. G. et al.: J. Pharmac. Biomed. Anal., 21, 1215 (2000); Bonafe, L. et al.: Mol. Gen. Metab., 69, 311 (2000); Sass, J. et al.: J. Inher. Metab. Dis., 27, 741 (2004);<br></p>

<p>Applications Caerulein is a ten amino acid oligopeptide that stimulates smooth muscle and increases digestive secretions. It is similar in action and composition to cholecystokinin. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle. It is used in paralytic ileus and as diagnostic aid in pancreatic malfunction. It is used to induce pancreatitis in experimental animal models.<br>References Anastasi,E., et al.: Ep., 23, 699 (1997); De Caro, G., et al.: Br. J. Pharmac Chemother., 33, 48 (1968)<br></p>

<p>Stability Hygroscopic<br>Applications (R)-3-Carboxy-2-hydroxy-N,N,N-trimethylpropan-1-aminium chloride is an important co-factor of mammalian mitochondrial energy metabolism. It is also a good active ingredient for dry-skin.<br>References Geier, David A., et al.: Neurochem. Res., 38(11), 2336-2341 (2013);Tanno, Osamu, et al.: Fragrance J., 33(8), 82-85 (2005);<br></p>

<p>Applications L-Aspartic Acid is a non-essential amino acid found in food sources. L-Aspartic Acid is one of the 20 proteinogenic amino acids; the building blocks of proteins. Its conjugate base L-aspartate is an excitatory neurotransmitter in the central nervous system.<br>References Ager, D.J. et al.: J. Mol. Catal. Enzym., 11, 199 (2001); Velisek, J. et al.: Cze. J. Food. Sci., 24, 1 (2006); Nagahama, M. et al.: Cell Tiss. Res., 318, 483 (2004);<br></p>

<p>Applications Myristoyl-L-carnitine Hydrochloride is a long-chain fatty ester of carnitine which is accumulated and released into the circulation, in fatty-acid oxidation defects. Pattern of Lauroyl-L-carnitine can be diagnostic for a number of ß-oxidation defects.<br>References Ventura, F., et al.: Clinica Chimica Acta, 281, 1 (1999); Pourfarzam, M., et al.: Clinical Chem,, 40, 2267 (1994); Schaefer, J., et al.: Pediatric Res., 37, 354 (1995)<br></p>

<p>Applications Hydroxyprolines are valuable chiral building blocks for organic synthesis of pharmaceuticals. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of trans-4- and cis-3-hydroxy-L-proline.<br>References Lawrence, C., et al.: Biochem. J., 313, 185 (1996), Mori, H., et al.: J. Bacteriol., 179, 5677 (1997), Clifton, I., et al.: Eur. J. Biochem., 268, 6625 (2001),<br></p>

<p>Applications L-Methionine-3,3,4,4-d4 (CAS# 67866-75-5) is a useful isotopically labeled research compound.<br></p>

<p>Applications A substrate for pyroglutamate aminopeptidase. Used for colorimetric determination of pyrrolidonyl peptidase activity in bacteria.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Szewczuk, A., et al.: Eur. J. Biochem., 8, 63 (1969), Szewczuk, A., et al.: Anal. Biochem., 39, 268 (1971)<br></p>

<p>Applications D-Serine Methyl Ester Hydrochloride (cas# 5874-57-7) is a compound useful in organic synthesis.<br></p>

<p>Applications N-Acetyl-L-glutamic Acid is the N-Acetyl analogue of the non-essential amino acid, L-glutamic acid (G596960). N-Acetyl-L-glutamic Acid activates carbamoyl phosphate synthetase in the urea cycle.<br>References Saheki, T. et al.: J. Biochem., 77, 659 (1975); Rivas, J. et al.: Acta Biol. Med. Ger., 36, 1673 (1977); Zollner, H.: Biochim. Biophys. Acta, 676, 170 (1981);<br></p>

<p>Applications A naturally occurring nitrostable secondary amine found in tabacco smoke condensate.<br>References Singer, G.M. et al.: J. Agric. Food Chem. 24, 553(1976); Bush, L. P. et al.: Can. J. Plant Sci. 50, 289(1970).<br></p>

<p>Stability Hygroscopic<br>Applications Cysteine is a non-essential amino acid that can be synthesized by the human body under normal physiological conditions if a sufficient quantity of methionine is available. Cysteine is commonly used as a precursor in the food and pharmaceutical industries. Cysteine is used as a processing aid for baking, as an additive in cigarettes, as well as in the preparation of meat flavours.<br>References Hui, N. et al.: Meat Sci. Appl., 74 (2001); Kiviharju, K. et al.: J. Biotechnol., 117, 299 (2005); Pecivova, P. et al.: J. Sci. Food Agric., 90, 1681 (2010);<br></p>

<p>Applications L-Serine is used in the synthesis of purines and pyrimidines as antibacterial/antifungal agents, as well as acting as a proteinogenic compound.<br>References Olivella, M. et al.: Bioorg. Med. Chem., 20, 6109 (2012);<br></p>

<p>Stability Moisture Sensitive<br>Applications 1-Acetate 4-Methanesulfonate 1,4-Butanediol is used in the facile cleavage of ethers. A Busulfan Impurity<br>References Mazur, Y., et al.: J. Org. Chem., 36, 532 (1971);<br></p>

<p>Applications Labelled 4-Methyl-2-oxovaleric Acid, an α-ketomonocarboxylic acid that triggers insulin release by acting upon receptor sites which differ from those occupied by amino acids. 4-Methyl-2-oxovaleric Acid is an intermediate in the metabolism of Leucine.<br>References Panten, U. et al.: Naun.-Schmied. Arch. Pharmacol., 291, 405 (1975); Vague, P. et al.: Diab. Metab., 1, 185 (1975); Francois, G. et al.: Lancet, 1, 858 (1984);<br></p>

<p>Applications Indole-3-acetyl-L-phenylalanine is an indole-3-acetyl-amino acid conjugate involved in regulatory mechanisms for the control of auxin activity during physiological and pathophysiological responses.<br>References Ostrowski, M., et al.: J Plant Physiol, 191, 63-72 (2016)<br></p>

<p>Stability Hygroscopic<br>Applications Dityrosine (DY), a tyrosine dimer formed by 3,3’-biaryl bond formation can be used as a biomarker to detect oxidative protein damage and selective proteolysis. Fluorescence intensity decays of Dityrosine are generally characterized by two decay components, one with a lifetime in the range of 150 to 800 ps and another between 2.5 and 4.5 ns.<br>References Libertini, L., et al.: Biophys. J., 47, 765 (1985), Huggins, T., et al.: J. Biol. Chem., 268, 12341 (1993), Malencik, D., et al.: Biochemistry, 35, 4375 (1996),<br></p>

<p>Applications L-Abrine is an indoleamino acid that displays radical scavenging and antioxidant properties.<br>References Yang, M., et al.: Food. Funct., 5, 2268 (2014);<br></p>

<p>Stability Hygroscopic<br>Applications 3-Chloro-L-tyrosine was used in the enzymatic synthesis of halogen derivatives of aromatic amino acids labeled with hydrogen isotope. 3-Chloro-L-tyrosine exhibited stronger antioxidant properties in Hb-induced oxidative stress as was evident by higher efficiency of reduction of ferryl species.<br>References Winnicka, E., et al.: J. Chem. Eng., 8, 54 (2014); Lu, N., et al.: Toxicol. In Vitro, 28, 847 (2014);<br></p>

<p>Applications 4-(1-Methylethyl)benzoic Acid is used in the synthesis of quinuclidine benzamides as agonists for nicotinic acetylcholine receptors. Also used in the synthesis of nifuroxazide analogues showing antimicrobial activity against methicillin-resistant Staphylococcus.<br>References Bodnar, A. et al.: J. Med. Chem., 48, 905 (2005); Masunari, A. et al.: Bioorg. Med. Chem. Lett., 15, 4229 (2007);<br></p>

<p>Applications (R)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.<br></p>

<p>Applications N-Pivaloylglycine is used in the biological study between dogs and rats. In a high dose toxicity study of pivalic acid (PA), PA caused skeletal muscle disorder in dog, and a significant increase of pivaloyl carnitine (PC) was observed in canine muscle, but not in rat muscle.<br>References Yamaguchi, T., et al.: Toxicol. Appl. Pharmacol., 214, 61-68 (2006)<br></p>

<p>Applications N-Boc-L-proline is a useful synthetic intermediate. It is used to synthesize Daclatasvir (D101500) which nhibits the HCV protein NS5A. Daclatasvir (D101500) can be used as a drug candidate for the treatment of hepatitis C (HCV).<br>References Gao, M., et al.: Nature, 465(7294), 96 (2010); Bell, T. W., Chem. Med. Chem., 5(10), 1663 (2010);<br></p>

<p>Applications Dihydro-5-methyl-4H-1,3,5-dithiazine is used as a reagent in the synthesis of neovibsanin derivatives which have the ability to induce neuronal differentiation in PC12 cells.<br>References Annette, P.-J. C., et al.: Tetrahedron, 66, 6842 (2010)<br></p>

<p>Stability Hygroscopic<br>Applications Labelled 3-Aminoisobutyric Acid (A611585). Substituted β-alanines. Used for preparation and isolation of D(-)-β-aminoisobutyric acid.<br>References Kakimoto, Y., et al.: J. Biol. Chem., 236, 3288 (1961),<br></p>

<p>Applications N-Carbamyl-L-glutamic Acid has been shown to have protective effects against ammonia intoxication and is used in the treatment of acute hyperammonemia.<br>References Paik, W.K. et al.: Life Sci., 15, 1189 (1974); O'Connor, J.E. et al.: Eur. J. Pediat., 148, 540 (1989); Lee, J.H. et al.: Biochem. Biophys. Res. Chem., 248, 391 (1998);<br></p>

<p>Stability Hygroscopic<br>Applications 3-Indolepropionic-d2 acid is deuterium labelled 3-Indolepropionic acid (I627170). 3-Indolepropionic acid is a deamination product of Tryptophan (T947200) that protects the hippocampus (studied in gerbils) from ischemic damage and oxidative stress. It’s ability to protect the neurons in this way is attributed to its potent antioxidative effects. 3-Indolepropionic acid is also hypothesized to have protective effects on the thyroid gland.<br>References Hwang, I., et al.: J. Neurosci. Res., 87, 2126 (2009); Karbownik, M., et al.: J. Cell. Biochem., 95, 131 (2005)<br></p>

<p>Applications L-(+)-2-Phenylglycine is a derivative of Glycine (G615990), the smallest of all the amino acids, and is also used to treat schizophrenia, stroke, and benign prostatic hyperplasia. L-(+)-2-Phenylglycine is also used as an N-linked side chain of an SMTP (Stachybotrys microspora tripenyl phenols) congener, which was potent in enhancing plasminogen activation in S. microspora.<br>References Gusev, E., et al.: Cerebrovasc. Dis., 10, 49 (2000); Koide, H., et al.: J. Antibiot., 65, 91 (2012); Rosse, R., et al.: Clin. Neuropharmacol., 12, 416 (1989); Tuszynski, G., et al.: Lab. Invest., 70, 228 (1994)<br></p>