Essential amino acid - wikipedia Essential amino acid See also : Protein ( nutrient ) An essential amino acid, or indispensable amino acid, is an amino acid that can not be synthesized de novo ( from scratch ) by the organism, and thus must be supplied in its diet. The nine amino acids humans can not synthesize are phenylalanine, valine, threonine, tryptophan, methionine, leucine, isoleucine, lysine, and histidine ( i.e., FVTWMLIKH ). Six other amino acids are considered conditionally essential in the human diet, meaning their synthesis can be limited under special pathophysiological conditions, such as prematurity in the infant or individuals in severe catabolic distress. These six are arginine, cysteine, glycine, glutamine, proline, and tyrosine ( i.e., RCGQPY ). Five amino acids are dispensable in humans, meaning they can be synthesized in sufficient quantities in the body. These five are alanine, aspartic acid, asparagine, glutamic acid and serine ( i.e., ADNES ). Contents 1 Essentiality in humans 2 Recommended daily intake 2.1 Relative amino acid composition of protein sources 2.2 Protein per calorie 3 Complete proteins in non-human animals 4 Interchangeability 5 Effects of deficiency 6 See also 7 References 8 External links Essentiality in humans Essential Conditionally essential Non-essential Histidine ( H ) Arginine ( R ) Alanine ( A ) Isoleucine ( I ) Cysteine ( C ) Aspartic acid ( D ) Leucine ( L ) Glutamine ( Q ) Asparagine ( N ) Lysine ( K ) Glycine ( G ) Glutamic acid ( E ) Methionine ( M ) Proline ( P ) Serine ( S ) Phenylalanine ( F ) Tyrosine ( Y ) Selenocysteine ( U ) Threonine ( T ) Pyrrolysine * ( O ) Tryptophan ( W ) Valine ( V ) ( * ) Pyrrolysine, sometimes considered the `` 22nd amino acid '', is not used by humans. Eukaryotes can synthesize some of the amino acids from other substrates. Consequently, only a subset of the amino acids used in protein synthesis are essential nutrients. Recommended daily intake Main article : Protein ( nutrient ) Estimating the daily requirement for the indispensable amino acids has proven to be difficult ; these numbers have undergone considerable revision over the last 20 years. The following table lists the WHO and United States recommended daily amounts currently in use for essential amino acids in adult humans, together with their standard one - letter abbreviations. Amino acid ( s ) WHO mg per kg body weight WHO mg per 70 kg US mg per kg body weight H Histidine 10 700 14 I Isoleucine 20 1400 19 L Leucine 39 2730 42 K Lysine 30 2100 38 M Methionine + C Cysteine 10.4 + 4.1 ( 15 total ) 1050 total 19 total F Phenylalanine + Y Tyrosine 25 ( total ) 1750 total 33 total T Threonine 15 1050 20 W Tryptophan 280 5 V Valine 26 1820 24 The recommended daily intakes for children aged three years and older is 10 % to 20 % higher than adult levels and those for infants can be as much as 150 % higher in the first year of life. Cysteine ( or sulfur - containing amino acids ), tyrosine ( or aromatic amino acids ), and arginine are always required by infants and growing children. Relative amino acid composition of protein sources Main article : Protein quality Various attempts have been made to express the `` quality '' or `` value '' of various kinds of protein. Measures include the biological value, net protein utilization, protein efficiency ratio, protein digestibility - corrected amino acid score and complete proteins concept. These concepts are important in the livestock industry, because the relative lack of one or more of the essential amino acids in animal feeds would have a limiting effect on growth and thus on feed conversion ratio. Thus, various feedstuffs may be fed in combination to increase net protein utilization, or a supplement of an individual amino acid ( methionine, lysine, threonine, or tryptophan ) can be added to the feed. Although plants tend to have less protein per weight than animal sources such as eggs or milk, they are nevertheless `` complete '' in that, as a whole, they contain all of the amino acids essential in human nutrition. The same is true for algae and marine phytoplankton. Eating various plant foods in combination can provide a protein of higher biological value. Certain native combinations of foods, such as corn and beans, soybeans and rice, or red beans and rice, contain the essential amino acids necessary for humans in adequate amounts. Protein per calorie Protein content in foods is often measured in protein per serving rather than protein per calorie. For instance, the USDA lists 6 grams of protein per large whole egg ( a 50 - gram serving ) rather than 84 mg of protein per calorie ( 71 calories total ). For comparison, there are 3 grams of protein in a serving of raw broccoli ( 91 grams ) or 96 mg of protein per calorie ( 31 calories total ). An egg contains twice as much protein per serving, but 12 mg less protein per calorie. The ratio of essential amino acids ( the quality of protein ) is not taken into account. It can be shown that common vegetable sources contain adequate protein, often more protein per calorie than the standard reference, whole raw egg, while other plant sources, particularly fruits contain less. It is recommended that adult humans obtain 10 -- 35 % of their calories as protein, or roughly 11 -- 39 mg of protein per cal per day ( 22 -- 78 g for 2000 cal ). A carrot has 23 mg protein per cal or twice the minimum recommendation, a banana meets the minimum, and an apple is below recommendation. Complete proteins in non-human animals Scientists had known since the early 20th century that rats could not survive on a diet whose only protein source was zein, which comes from maize ( corn ), but recovered if they were fed casein from cow 's milk. This led William Cumming Rose to the discovery of the essential amino acid threonine. Through manipulation of rodent diets, Rose was able to show that ten amino acids are essential for rats : lysine, tryptophan, histidine, phenylalanine, leucine, isoleucine, methionine, valine, and arginine, in addition to threonine. Rose 's later work showed that eight amino acids are essential for adult human beings, with histidine also being essential for infants. Longer term studies established histidine as also essential for adult humans. Interchangeability The distinction between essential and non-essential amino acids is somewhat unclear, as some amino acids can be produced from others. The sulfur - containing amino acids, methionine and homocysteine, can be converted into each other but neither can be synthesized de novo in humans. Likewise, cysteine can be made from homocysteine but can not be synthesized on its own. So, for convenience, sulfur - containing amino acids are sometimes considered a single pool of nutritionally equivalent amino acids as are the aromatic amino acid pair, phenylalanine and tyrosine. Likewise arginine, ornithine, and citrulline, which are interconvertible by the urea cycle, are considered a single group. Effects of deficiency Main article : Protein - energy malnutrition If one of the essential amino acids is less than needed for an individual the utilization of other amino acids will be hindered and thus protein synthesis will be less than what it usually is, even in the presence of adequate total nitrogen intake. Protein deficiency has been shown to affect all of the body 's organs and many of its systems, including the brain and brain function of infants and young children ; the immune system, thus elevating risk of infection ; gut mucosal function and permeability, which affects absorption and vulnerability to systemic disease ; and kidney function. The physical signs of protein deficiency include edema, failure to thrive in infants and children, poor musculature, dull skin, and thin and fragile hair. Biochemical changes reflecting protein deficiency include low serum albumin and low serum transferrin. The amino acids that are essential in the human diet were established in a series of experiments led by William Cumming Rose. The experiments involved elemental diets to healthy male graduate students. These diets consisted of cornstarch, sucrose, butterfat without protein, corn oil, inorganic salts, the known vitamins, a large brown `` candy '' made of liver extract flavored with peppermint oil ( to supply any unknown vitamins ), and mixtures of highly purified individual amino acids. The main outcome measure was nitrogen balance. Rose noted that the symptoms of nervousness, exhaustion, and dizziness were encountered to a greater or lesser extent whenever human subjects were deprived of an essential amino acid. Essential amino acid deficiency should be distinguished from protein - energy malnutrition, which can manifest as marasmus or kwashiorkor. Kwashiorkor was once attributed to pure protein deficiency in individuals who were consuming enough calories ( `` sugar baby syndrome '' ). However, this theory has been challenged by the finding that there is no difference in the diets of children developing marasmus as opposed to kwashiorkor. Still, for instance in Dietary Reference Intakes ( DRI ) maintained by the USDA, lack of one or more of the essential amino acids is described as protein - energy malnutrition. See also Biological Value ( BV ) Edible protein per unit area of land Essential fatty acid Essential genes List of standard amino acids Low - protein diet Orthomolecular medicine Protein Digestibility Corrected Amino Acid Score Ketogenic amino acid Glucogenic amino acid References Jump up ^ Young VR ( 1994 ). `` Adult amino acid requirements : the case for a major revision in current recommendations '' ( PDF ). J. Nutr. 124 ( 8 Suppl ) : 1517S -- 1523S. PMID 8064412. ^ Jump up to : Dietary Reference Intakes : The Essential Guide to Nutrient Requirements Archived 5 July 2014 at the Wayback Machine... Institute of Medicine 's Food and Nutrition Board. usda.gov Jump up ^ Fürst P, Stehle P ( 1 June 2004 ). `` What are the essential elements needed for the determination of amino acid requirements in humans ? ''. Journal of Nutrition. 134 ( 6 Suppl ) : 1558S -- 1565S. PMID 15173430. Jump up ^ Reeds PJ ( 1 July 2000 ). `` Dispensable and indispensable amino acids for humans ''. J. Nutr. 130 ( 7 ) : 1835S -- 40S. PMID 10867060. Jump up ^ Richard Cammack. `` Newsletter 2009, Biochemical Nomenclature Committee of IUPAC and NC - IUBMB ''. ^ Jump up to : FAO / WHO / UNU ( 2007 ). `` PROTEIN AND AMINO ACID REQUIREMENTS IN HUMAN NUTRITION '' ( PDF ). WHO Press., page 150 Jump up ^ Institute of Medicine ( 2002 ). `` Protein and Amino Acids ''. Dietary Reference Intakes for Energy, Carbohydrates, Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids. Washington, DC : The National Academies Press. pp. 589 -- 768. Jump up ^ Imura K, Okada A ( 1998 ). `` Amino acid metabolism in pediatric patients ''. Nutrition. 14 ( 1 ) : 143 -- 8. doi : 10.1016 / S0899 - 9007 ( 97 ) 00230 - X. PMID 9437700. Jump up ^ McDougall J. Plant foods have a complete amino acid composition. Circulation. 2002 ; 105 ( 25 ) : e197 Jump up ^ Woolf, P.J. ; Fu, L.L. ; Basu, A. ( 2011 ). Haslam, Niall James, ed. `` VProtein : Identifying Optimal Amino Acid Complements from Plant - Based Foods ''. PLoS ONE. 6 ( 4 ) : e18836. doi : 10.1371 / journal. pone. 0018836. PMC 3081312. PMID 21526128. Jump up ^ Essential Amino Acids. phy-astr.gsu.edu : `` Tillery points out that a number of popular ethnic foods involve such a combination, so that in a single dish, one might hope to get the ten essential amino acids. Mexican corn and beans, Japanese rice and soybeans, and Cajun red beans and rice are examples of such fortuitous combinations. '' Jump up ^ SDA National Nutrient Database for Standard Reference ( Release 21 ed. ). U.S. Department of Agriculture, Agricultural Research Service. 2008. Jump up ^ `` Web MD Protein : Are You Getting Enough ? ''. webmd.com. 2014 - 09 - 05. Retrieved 2015 - 03 - 31. Jump up ^ `` USDA National Nutrient Database ''. USDA.gov. 2015 - 03 - 31. Retrieved 2015 - 03 - 31. Jump up ^ Rose WC, Haines WJ, Warner DT, Johnson JE ( 1951 ). `` The amino acid requirements of man. II. The role of threonine and histidine ''. The Journal of Biological Chemistry. 188 ( 1 ) : 49 -- 58. PMID 14814112. Jump up ^ Kopple JD, Swendseid ME ( May 1975 ). `` Evidence that histidine is an essential amino acid in normal and chronically uremic man ''. J Clin Invest. 55 ( 5 ) : 881 -- 891. doi : 10.1172 / JCI108016. PMC 301830. PMID 1123426. Jump up ^ Rose, WC ; Haines, WJ ; Warner, DT ( 1951 ). `` The amino acid requirements of man. III. The role of isoleucine ; additional evidence concerning histidine '' ( PDF ). J Biol Chem. 193 ( 2 ) : 605 -- 612. PMID 14907749. Retrieved 15 Dec 2012. Jump up ^ Ahmed T, Rahman S, Cravioto A ( 2009 ). `` Oedematous malnutrition ''. The Indian journal of medical research. 130 ( 5 ) : 651 -- 4. PMID 20090122. External links Amino acid content of some vegetarian foods at veganhealth.org. Amino Acid Profiles of Some Common Feeds at Virginia Tech. Molecular Expressions : The Amino Acid Collection at Florida State University. Features detailed information and crystal photographs of each amino acid. vProtein, an online software tool to analyze the essential amino acid profiles of single and pairs of plant based foods based on human requirements. Encoded ( proteinogenic ) amino acids General topics Protein Peptide Genetic code By properties Aliphatic Branched - chain amino acids ( Valine Isoleucine Leucine ) Methionine Alanine Proline Glycine Aromatic Phenylalanine Tyrosine Tryptophan Histidine Polar, uncharged Asparagine Glutamine Serine Threonine Positive charge ( pK ) Lysine ( ≈ 10.8 ) Arginine ( ≈ 12.5 ) Histidine ( ≈ 6.1 ) Negative charge ( pK ) Aspartic acid ( ≈ 3.9 ) Glutamic acid ( ≈ 4.1 ) Cysteine ( ≈ 8.3 ) Tyrosine ( ≈ 10.1 ) Amino acids types : Encoded ( proteins ) Essential Non-proteinogenic Ketogenic Glucogenic Imino acids D - amino acids Dehydroamino acids Retrieved from `` https://en.wikipedia.org/w/index.php?title=Essential_amino_acid&oldid=847973397 '' Categories : Amino acids Essential amino acids Nitrogen cycle Nutrition Hidden categories : Webarchive template wayback links All articles with unsourced statements Articles with unsourced statements from July 2014 Use dmy dates from February 2011 Talk Contents About Wikipedia Bân - lâm - gú Беларуская Български Bosanski Català Čeština Dansk Deutsch Eesti Ελληνικά Español Esperanto Euskara فارسی Français Galego 한국어 Հայերեն Hrvatski Italiano Lietuvių Монгол Nederlands 日本 語 Occitan Polski Português Română Русский Slovenčina Slovenščina Српски / srpski Srpskohrvatski / српскохрватски Suomi Svenska ไทย Українська Tiếng Việt 中文 31 more Edit links This page was last edited on 29 June 2018, at 00 : 58 ( UTC ). 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Question: amino acids that you obtain from eating foods are classified as
Answer: essential amino acid