Homoserine: Difference between revisions

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[[File:HomoserineBiosyn.png|thumb]] [[File:Homoserine biosyntheses.png|thumb]] {{Short description|An amino acid intermediate in the biosynthesis of several essential amino acids}}
{{Infobox chemical
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477239870
| ImageFile = Homoserine.png
| ImageSize = 150px
| ImageAlt = Skeletal formula of homoserine
| ImageFile1 = Homoserine zwitterion.png
| ImageSize1 = 150px
| ImageAlt1 = Skeletal formula of the zwitterionic form of homoserine
| IUPACName = 2-Amino-4-hydroxybutanoic acid
| OtherNames = Homoserine
| Section1 = {{Chembox Identifiers
| CASNo = 672-15-1
| PubChem = 5961
| ChemSpiderID = 5744
| UNII = 8T8I0ZRA2W
| ChEBI = 16899
| ChEMBL = 12345
| SMILES = C(C(C(=O)O)N)CO
| InChI = 1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)
| InChIKey = QIVBCDIJIAJPQS-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C = 4
| H = 9
| N = 1
| O = 3
| MolarMass = 119.12 g/mol
| MeltingPt = 190 °C
}}
}}


'''Homoserine''' is an α-amino acid with the chemical formula C₄H₉NO₃. It is an intermediate in the biosynthesis of several essential amino acids, including [[threonine]], [[methionine]], and [[isoleucine]]. Homoserine is not one of the standard amino acids encoded by the genetic code, but it plays a crucial role in the metabolic pathways of many organisms.
'''Homoserine''' is an [[α-amino acid]] with the chemical formula HO2CCH(NH2)CH2CH2OH. It is not one of the common [[proteinogenic amino acids]] but is an important intermediate in the [[biosynthesis]] of several essential amino acids, including [[methionine]], [[threonine]], and [[isoleucine]].


==Structure and Properties==
== Biosynthesis ==
Homoserine is structurally similar to the amino acid [[serine]], with an additional methylene group in its side chain. This gives homoserine the chemical structure of 2-amino-4-hydroxybutanoic acid. It is a non-proteinogenic amino acid, meaning it is not incorporated into proteins during translation.
Homoserine is synthesized from [[aspartic acid]] via a series of enzymatic reactions. The pathway begins with the phosphorylation of aspartic acid to form [[aspartyl phosphate]], which is then reduced to [[aspartate semialdehyde]]. This intermediate is further reduced to homoserine by the enzyme [[homoserine dehydrogenase]].


==Biosynthesis==
== Role in Metabolism ==
Homoserine is synthesized from [[aspartate]] through a series of enzymatic reactions. The pathway begins with the phosphorylation of aspartate to form aspartyl-phosphate, which is then reduced to form aspartate-β-semialdehyde. This intermediate is converted to homoserine by the enzyme homoserine dehydrogenase.
In [[microorganisms]] and [[plants]], homoserine serves as a precursor to several essential amino acids. The conversion of homoserine to [[threonine]] involves the enzyme [[threonine synthase]], while its conversion to [[methionine]] involves a series of steps including the enzyme [[homoserine O-succinyltransferase]].


===Role in Amino Acid Biosynthesis===
== Industrial Applications ==
Homoserine serves as a precursor for the synthesis of several essential amino acids:
Homoserine and its derivatives are used in the production of [[biodegradable plastics]] and as precursors in the synthesis of various [[pharmaceuticals]].


* '''Threonine''': Homoserine is phosphorylated to form O-phosphohomoserine, which is then converted to threonine by threonine synthase.
== See Also ==
* '''Methionine''': Homoserine is first converted to O-phosphohomoserine, which is then transformed into cystathionine and subsequently into methionine through a series of reactions.
* [[Amino acid synthesis]]
* '''Isoleucine''': In some organisms, homoserine can be converted into isoleucine through a series of transamination and reduction reactions.
* [[Metabolic pathway]]
* [[Essential amino acid]]


==Biological Importance==
== References ==
Homoserine is a key intermediate in the metabolic pathways that produce essential amino acids. These amino acids are vital for protein synthesis and various metabolic functions in organisms. Since humans cannot synthesize these essential amino acids, they must be obtained through the diet.
{{Reflist}}


==Industrial and Research Applications==
== External Links ==
Homoserine and its derivatives are used in research to study metabolic pathways and enzyme functions. Understanding the role of homoserine in amino acid biosynthesis can lead to advances in biotechnology, such as the development of genetically engineered organisms for the production of essential amino acids.
* [https://www.wikimd.com/wiki/Homoserine Homoserine on WikiMD]
 
==Also see==
* [[Amino acid biosynthesis]]
* [[Threonine]]
* [[Methionine]]
* [[Isoleucine]]
* [[Aspartate]]
 
{{Amino acids}}


[[Category:Amino acids]]
[[Category:Amino acids]]
[[Category:Biochemistry]]
[[Category:Biochemistry]]
[[Category:Metabolism]]
[[Category:Metabolism]]

Latest revision as of 20:49, 30 December 2024

Chemical Compound
Identifiers
CAS Number
PubChem CID
ChemSpider ID
UNII
ChEBI
ChEMBL
Properties
Chemical Formula
Molar Mass
Appearance
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Melting Point
Boiling Point
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GHS Pictograms [[File:|50px]]
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References

Homoserine is an α-amino acid with the chemical formula HO2CCH(NH2)CH2CH2OH. It is not one of the common proteinogenic amino acids but is an important intermediate in the biosynthesis of several essential amino acids, including methionine, threonine, and isoleucine.

Biosynthesis[edit]

Homoserine is synthesized from aspartic acid via a series of enzymatic reactions. The pathway begins with the phosphorylation of aspartic acid to form aspartyl phosphate, which is then reduced to aspartate semialdehyde. This intermediate is further reduced to homoserine by the enzyme homoserine dehydrogenase.

Role in Metabolism[edit]

In microorganisms and plants, homoserine serves as a precursor to several essential amino acids. The conversion of homoserine to threonine involves the enzyme threonine synthase, while its conversion to methionine involves a series of steps including the enzyme homoserine O-succinyltransferase.

Industrial Applications[edit]

Homoserine and its derivatives are used in the production of biodegradable plastics and as precursors in the synthesis of various pharmaceuticals.

See Also[edit]

References[edit]

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External Links[edit]

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