Essential amino acid

See also: Protein (nutrient)

An essential amino acid or indispensable amino acid is an amino acid that cannot be synthesized de novo (from scratch) by the organism, but must be supplied in its diet. The nine amino acids humans cannot synthesize are phenylalanine, valine, threonine, tryptophan, methionine, leucine, isoleucine, lysine, and histidine (i.e., F V T W M L I K H).

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. R C G Q P Y). Five amino acids are dispensable in humans, meaning they can be synthesized in the body. These five are alanine, aspartic acid, asparagine, glutamic acid and serine (i.e., A D N E S).

Essentiality in humans

Essential	Nonessential **
Histidine	Alanine
Isoleucine	Arginine*
Leucine	Aspartic acid
Lysine	Cysteine*
Methionine	Glutamic acid
Phenylalanine	Glutamine*
Threonine	Glycine*
Tryptophan	Proline*
Valine	Serine*
	Tyrosine*
	Asparagine*
	Selenocysteine

(*) Essential only in certain cases.

(**) Pyrrolysine, sometimes considered "the 22nd amino acid", is not listed here as it 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.

Minimum 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 recommended daily amounts currently in use for essential amino acids in adult humans, together with their standard one-letter abbreviations. Food sources are identified based on the USDA National Nutrient Database Release.

Amino acid(s)	mg per kg body weight	mg per 70 kg	mg per 100 kg
H Histidine	10	700	1000
I Isoleucine	20	1400	2000
L Leucine	39	2730	3900
K Lysine	30	2100	3000
M Methionine + C Cysteine	10.4 + 4.1 (15 total)	1050	1500
F Phenylalanine + Y Tyrosine	25 (total)	1750	2500
T Threonine	15	1050	1500
W Tryptophan	4	280	400
V Valine	26	1820	2600

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 sulphur-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

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 protein 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 proteins from plant sources tend to have a relatively lower concentrations of protein by mass in comparison to protein from eggs or milk, they are nevertheless "complete" in that they contain at least trace amounts of all of the amino acids that are essential in human nutrition. 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.

Additionally, certain types of algae and marine phytoplankton predate the division between animal and plant life on the planet; they have both chlorophyll as do plants, and also all the essential amino acids, as do animal proteins.

Protein per calorie

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. For example, while 100 g of raw broccoli only provides 28 kcal and 3 g of protein, it has over 100 mg of protein per kcal. An egg contains five times as many calories (143 kcal) but only four times as much protein, roughly 90 mg of protein per kcal. However, a carrot has only 23 mg protein per kcal or twice the minimum recommendation, a banana meets the minimum, and an apple is below recommendation. It is recommended that adult humans obtain 10-35% of their calories as protein, or roughly 11–39 mg of protein per kcal per day (22-78 g for 2000 kcal). The US FDA daily reference value of 50 g protein per 2000 kcal is 25 mg/kcal per day.

Source	protein (g)	Calories (kcal)	protein/Calorie (mg / kcal)	L (mg)	T (mg)	W (mg)	M+C (mg)
Apples, raw (100 g)	0.26	52	5	12	6	1	2
Minimum daily reference	22	2000	11
Bananas, raw (100 g)	1	89	12	500	28	9	17
Carrot, raw (100 g)	1	41	23	101	191	12	103
US FDA daily / WHO (70 kg)	50	2000	25	2730	1050	280	1050
Upper daily reference	78	2000	39
Peanut, valencia, raw (100 g)	48	570	84	1,627	859	244	630
Soybeans, dry (100 g)	40	451	88	2634	1719	575	1172
Egg, whole, raw (100 g)	13	143	91	912	556	167	652
Broccoli, raw (100 g)	3	28	107	141	91	29	54
Soy Sauce, typical (100 g)	11	60	175	729	403	182	576
Beef, grass-fed, lean (100 g)	23	117	197

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 cannot 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 nonessential 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 DRIs maintained by the USDA, lack of one or more of the essential amino acids is described as protein-energy malnutrition.

Mnemonics

Using the one-letter designation shown above, mnemonic devices have been developed for use in memorizing the essential amino acids. Previous devices have utilized the first letter of the amino acids' names, and in general did not include arginine which is not always essential. Mnemonic devices in common use are PVT TIM HaLL and TT HaLL V(ery) IMP(ortant).

Another method uses the first letter of each essential amino acid to begin each word in a phrase, such as: "Any Help In Learning These Little Molecules Proves Truly Valuable". This method begins with the two amino acids that need some qualifications as to their requirements.

See also

• Biological Value (BV)
• Complete protein
• 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

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.