Information about Essential Amino Acid

An essential amino acid or indispensable amino acid is an amino acid that cannot be synthesized de novo by the organism (usually referring to humans), and therefore must be supplied in the diet.

Essentiality vs. conditional essentiality in humans

Nine amino acids are generally regarded as essential for humans: isoleucine, leucine, lysine, threonine, tryptophan, methionine, histidine, valine and phenylalanine. In addition, the amino acids arginine, cysteine, glycine, glutamine and tyrosine are considered conditionally essential, meaning they are not normally required in the diet, but must be supplied exogenously to specific populations that do not synthesize it in adequate amounts. An example would be with the disease phenylketonuria (PKU). Individuals living with PKU must keep their intake of phenylalanine extremely low to prevent mental retardation and other metabolic complications. However, phenylalanine is the precursor for tyrosine synthesis. Without phenylalanine, tyrosine cannot be made and so tyrosine becomes essential in the diet of PKU patients.

Which amino acids are essential varies from species to species, as different metabolisms are able to synthesize different substances. For instance, taurine (which is not, by strict definition, an amino acid) is essential for cats, but not for dogs. Thus, dog food is not nutritionally sufficient for cats, and taurine is added to commercial cat food, but not to dog food.

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. Likewise arginine, ornithine, and citrulline, which are interconvertible by the urea cycle, are considered a single group.

Recommended daily amounts

The following table lists the recommended daily amounts for essential amino acids in humans, together with their standard one-letter abbreviations.[1] In some cases, humans can use either of two amino acids, so only the total matters.
Amino acid WHO-recommended daily intake for human adults, mg per kg body weight mg per 70 kg
F Phenylalanine + Y Tyrosine14 (total)980
L Leucine14980
M Methionine + C Cysteine13 (total)910
K Lysine12840
I Isoleucine10700
V Valine10700
T Threonine7490
W Tryptophan3245
H Histidineunknown, 28 in infants (? sum with arginine)(? 1960)
R Arginineunknown, required for infants, maybe seniors(?)


Taurine may be necessary to preserve arterial and collagen pliability at 2 mg/kg/day, small but needed (142 mg/day per 70 kg human).

Use of essential amino acids

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Foodstuffs that lack essential amino acids are poor sources of protein equivalents, as the body tends to deaminate the amino acids obtained, converting proteins into fats and carbohydrates[2]. Therefore, a balance of essential amino acids is necessary for a high degree of net protein utilization, which is the mass ratio of amino acids converted to proteins to amino acids supplied.

All essential amino acids may be obtained from plant sources, and even strict vegetarian diets can provide all dietary requirements, although most vegetarians may not be so thorough. Some believe that careful monitoring of nutrient levels is important in strict vegetarian diets, but there are virtually no cases of protein-deficiency among populations consuming adequate calories. The only common cases of protein-deficiency occur among populations that are chronically undernourished.

The net protein utilization is profoundly affected by the limiting amino acid content (the essential amino acid found in the smallest quantity in the foodstuff), and somewhat affected by salvage of essential amino acids in the body. It is therefore a good idea to mix foodstuffs that have different weaknesses in their essential amino acid distributions. This limits the loss of nitrogen through deamination and increases overall net protein utilization.

Protein source Limiting amino acid
Wheatlysine
Ricelysine
Legumestryptophan
Maizelysine and tryptophan
Pulsesmethionine (or cysteine)
Beefphenylalanine (or tyrosine)
Egg, chickennone; the reference for absorbable protein
Milk or Whey, bovinemethionine (or cysteine)

Mnemonics

Using the one letter designation shown above, mnemonic devices have been developed for students wanting or needing to memorize the essential amino acids. Previous devices have utilized the first letter of the amino acids name, and in general did not include arginine which is not always essential. One mnemonic device that has been used in the past is PVT TIM HALL.[3]

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."[4] This method begins with the two amino acids that need some qualifications as to their requirements.

Note that these devices work by using the first letter of the actual amino acids name. Due to repetition of letters, several amino acids have one letter abbreviations that are different than their first letter (e.g. lysine is K). Thus the complete list of essential amino acids utilizing one-letter codes is MILKVWTHFR.

See also

References

1. ^ WHO table of required proportions of amino acids at oralchelation.com
2. ^ McGilvery, Robert W. Biochemistry, a Functional Approach 1979. Chapter 41, esp Page 787
3. ^ Mnemonic at medicalmnemonics.com 442 128 |
4. ^ Williams, R.A.D.; Eliot, J.C. (1989). Basic and Applied Dental Biochemistry. Elsevier Health Sciences, p.149. ISBN 0443031444. 

External links

amino acid is a molecule that contains both amine and carboxyl functional groups. In biochemistry, this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent.
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De novo synthesis refers to the synthesis of complex molecules from simple molecules such as sugars or amino acids, as opposed to their being recycled after partial degradation. For example, de novo synthesis of nucleotides is an alternative to the salvage pathway.
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Isoleucine (abbreviated as Ile or I)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH(CH3)CH2CH3.
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Leucine (abbreviated as Leu or L)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CH(CH3)2. It is an essential amino acid, which means that humans cannot synthesise it.
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Lysine (abbreviated as Lys or K)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)(CH2)4NH2.
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Threonine (abbreviated as Thr or T)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH(OH)CH3. Its codons are ACU and ACA. This essential amino acid is classified as polar.
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Tryptophan (abbreviated as Trp or W)[1] is an essential amino acid involved in human nutrition. It is one of the 20 amino acids encoded by the genetic code (as codon UGG).
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Methionine (abbreviated as Met or M)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CH2SCH3. This essential amino acid is classified as nonpolar.
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Histidine (abbreviated as His or H)[1] is one of the 20 most common natural amino acids present in proteins. In the nutritional sense, in humans, histidine is considered an essential amino acid, but mostly only in children.
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Valine (abbreviated as Val or V)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH(CH3)2. L-Valine is one of 20 proteogenic amino acids. Its codons are GUU, GUC, GUA, and GUG.
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Phe redirects here. For the BitTorrent feature, see PHE. For the constellation, see Phoenix (constellation).


Phenylalanine (abbreviated as Phe or F)[1] is an α-amino acid with the formula HO2
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Arginine (abbreviated as Arg or R)[1] is an α-amino acid. The L -form is one of the 20 most common natural amino acids. Its codons are CGU, CGC, CGA and CGG.
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Cysteine (abbreviated as Cys or C)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH2SH. It is not an essential amino acid, which means that humans can synthesize it. Its codons are UGU and UGC.
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Glycine (abbreviated as Gly or G)[1] is the organic compound with the formula HO2CCH2NH2.
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Glutamine (abbreviated as Gln or Q; Glx or Z represents either glutamine or glutamic acid) is one of the 20 amino acids encoded by the standard genetic code.
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Tyrosine (abbreviated as Tyr or Y)[1] or 4-hydroxyphenylalanine, is one of the 20 amino acids that are used by cells to synthesize proteins. It is a non-essential amino acid and it is found in large quantities in casein.
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Phenylketonuria
Classification & external resources

Phenylalanine
ICD-10 E 70.0
ICD-9 270.1

OMIM 261600
DiseasesDB 9987
MedlinePlus 001166
eMedicine ped/1787   derm/712
MeSH D010661 Phenylketonuria (PKU
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Taurine, or 2-aminoethanesulfonic acid, is an organic acid that is a major constituent of bile, and can be found in lower amounts in the tissues of many animals including humans.
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Taurine, or 2-aminoethanesulfonic acid, is an organic acid that is a major constituent of bile, and can be found in lower amounts in the tissues of many animals including humans.
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6
(strongly acidic oxide)
Electronegativity 2.58 (Pauling scale)
Ionization energies
(more) 1st: 999.6 kJmol−1
2nd: 2252 kJmol−1
3rd: 3357 kJmol−1

Atomic radius 100 pm
Atomic radius (calc.
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Methionine (abbreviated as Met or M)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CH2SCH3. This essential amino acid is classified as nonpolar.
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Homocysteine is a chemical compound with the formula HSCH2CH2CH(NH2)CO2H. It is a homologue of the naturally-occurring amino acid cysteine, differing in that its side-chain contains an additional methylene (-CH2
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Arginine (abbreviated as Arg or R)[1] is an α-amino acid. The L -form is one of the 20 most common natural amino acids. Its codons are CGU, CGC, CGA and CGG.
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Ornithine is an amino acid, whose structure is:

NH2-CH2-CH2-CH2-CHNH2-COOH

Role in urea cycle

Ornithine is one of the products of the action of the enzyme arginase on L-arginine, creating urea.
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The organic compound citrulline is an α-amino acid. Its name is derived from citrullus, the Latin word for watermelon, from which it was first isolatedin 1930.
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The urea cycle (also known as the ornithine cycle) is a cycle of biochemical reactions occurring in many animals that produces urea from ammonia (NH3). This cycle was the first metabolic cycle discovered (Krebs and Kurt Henseleit, 1932).
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WHO may stand for:
  • World Health Organization
  • WHO (AM), a radio station in Des Moines, Iowa, United States
  • WHO-TV, television station in Des Moines owned by Local TV LLC
  • Washington Homeschool Organization, a homeschool group in the US state of Washington

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Phe redirects here. For the BitTorrent feature, see PHE. For the constellation, see Phoenix (constellation).


Phenylalanine (abbreviated as Phe or F)[1] is an α-amino acid with the formula HO2
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Tyrosine (abbreviated as Tyr or Y)[1] or 4-hydroxyphenylalanine, is one of the 20 amino acids that are used by cells to synthesize proteins. It is a non-essential amino acid and it is found in large quantities in casein.
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Leucine (abbreviated as Leu or L)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CH(CH3)2. It is an essential amino acid, which means that humans cannot synthesise it.
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