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14-September-2008 18:38:48 - Cystine Skeletal formula of cystine formed from L-cysteine under biological conditions Skeletal formula of cystine formed from L-cysteine under biological conditions Ball-and-stick model of cystine with the disulfide bond shown in yellow Ball-and-stick model of cystine with the disulfide bond shown in yellow Cystine Systematic IUPAC name Cystine Identifiers PubChem ? Chemical data Formula C6H12N2O4S2 Molar mass 240.30 Complete data Cystine is the amino acid dimer formed when a pair of cysteine molecules are joined by a disulfide bond. It is described by the formula SCH2CHNH2CO2H2. It is a colorless solid, and melts at 247-249 °C. It was discovered in 1810 by William Hyde Wollaston but was not recognized as a component of proteins until it was isolated from the horn of a cow in 1899.1 Through formation of disulfide bonds within and between protein molecules, cystine is a significant determinant of the tertiary structure of most proteins. Disulfide bonding, along with hydrogen bonding and hydrophobic interactions is partially responsible for the formation of the gluten matrix in bread. Human hair contains approximately 5% cystine by mass.2 Contents 1 Properties 2 Nutritional sources 2.1 In animal feed 3 Side effects 4 See also 5 References 6 External links Properties The disulfide link is readily reduced to give the corresponding thiol, cysteine. This reaction is typically effected with thiols such as mercaptoethanol or dithiothreitol. SCH2CHNH2CO2H2 + 2 RSH → 2 HSCH2CHNH2CO2H + RSSR Nutritional sources Supplemental N-acetyl cysteine is claimed to be a source of cystine, but the dose of this supplement is limited by side effects. One of the richest nutritional sources of cystine in the diet is undenatured whey proteins from milk. The disulfide-bonded cystine is not digested or significantly hydrolized by the stomach, but is transported by the blood stream to the tissues of the body. Here, within the cells of the body, the weak disulfide bond is cleaved to give cysteine, from which glutathione can be synthesized. In animal feed Disulfide bonds can be broken at temperatures above about 150 °C, especially at low moisture levels below about 20%3. Side effects Nutritional sources of cystine are virtually free of the toxic side effects associated with the single molecule of cysteine, N-acetyl cysteine. The greatest dietary source of cystine is bio-active, unpasteurized or low-heat pasteurized undenatured whey proteins.citation needed See also Cystinuria Cysteine References ^ cystine. Encyclopædia Britannica. 2007. Encyclopædia Britannica Online. 27 July 2007 www.britannica.com/eb/article-9028437/cystine ^ Gortner, R. A.; W. F. Hoffman, W. F. 1941. l-Cystine. Org. Synth.; Coll. Vol. 1: 194. ^ M.A. Aslaksena, O.H. Romarheima, T. Storebakkena and A. Skrede 28 June 2006. Evaluation of content and digestibility of disulfide bonds and free thiols in unextruded and extruded diets containing fish meal and soybean protein sources. Animal Feed Science and Technology 128 3-4: 320-330. doi:10.1016/j.anifeedsci.2005.11.008. External links v d e E numbers Colours E100-199 Preservatives E200-299 Antioxidants Acidity regulators E300-399 Thickeners, stabilisers emulsifiers E400-499 pH regulators anti-caking agents E500-599 Flavour enhancers E600-699 Miscellaneous E900-999 Additional chemicals E1100-1599 Waxes E900-909 Synthetic glazes E910-919 Improving agents E920-929 Packaging gases E930-949 Sweeteners E950-969 Foaming agents E990-999 L-cysteine E920 L-cystine E921 Potassium persulfate E922 Ammonium persulfate E923 Potassium bromate E924 Chlorine E925 Chlorine dioxide E926 Azodicarbonamide E927 Carbamide E927b Benzoyl peroxide E928 Retrieved from http://en..org/wiki/Cystine Categories: Organic disulfides | Sulfur amino acidsHidden categories: All articles with statements | Articles with statements since June 2007 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages العربية Deutsch Español Français Italiano Nederlands 日本語 Polski Português This page was last modified on 11 July 2008, at 10:36
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