Homoserine: Difference between revisions

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[[file:HomoserineBiosyn.png|thumb|HomoserineBiosyn]] [[file:Homoserine_biosyntheses.png|thumb|Homoserine biosyntheses|left]] {{Short description|A non-proteinogenic amino acid}}
{{Infobox chemical
{{Infobox chemical
| verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 477002318
| verifiedrevid = 477239870
| name = Homoserine
| ImageFile = Homoserine.png
| image = Homoserine.png
| ImageSize = 150px
| image2 = Homoserine-3D-balls.png
| ImageAlt = Skeletal formula of homoserine
| pin = (2S)-2-Amino-4-hydroxybutanoic acid
| ImageFile1 = Homoserine zwitterion.png
| othernames =  
| ImageSize1 = 150px
| section1 =  
| ImageAlt1 = Skeletal formula of the zwitterionic form of homoserine
 
| IUPACName = 2-Amino-4-hydroxybutanoic acid
| section2 =  
| OtherNames = Homoserine
 
| Section1 = {{Chembox Identifiers
| section3 =  
| CASNo = 672-15-1
 
| PubChem = 5961
| section4 =  
| ChemSpiderID = 5744
 
| UNII = 8T8I0ZRA2W
| section5 =  
| ChEBI = 16899
 
| ChEMBL = 12345
| section6 =  
| 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)
| section7 =  
| InChIKey = QIVBCDIJIAJPQS-UHFFFAOYSA-N
 
}}
| section8 =  
| Section2 = {{Chembox Properties
 
| C = 4
| section9 =  
| H = 9
 
| N = 1
| section10 =  
| O = 3
 
| MolarMass = 119.12 g/mol
| section11 =  
| MeltingPt = 190 °C
 
}}
| section12 =  
}}
 
| section13 =  
 
| section14 =


| section15 =
'''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]].


| section16 =  
== Biosynthesis ==
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 ==
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]].


'''Homoserine''' is a [[non-proteinogenic amino acid]] with the chemical formula C<sub>4</sub>H<sub>9</sub>NO<sub>3</sub>. It is an intermediate in the [[biosynthesis]] of [[methionine]], [[threonine]], and [[isoleucine]].
== Industrial Applications ==
Homoserine and its derivatives are used in the production of [[biodegradable plastics]] and as precursors in the synthesis of various [[pharmaceuticals]].


==Structure and Properties==
== See Also ==
Homoserine is structurally similar to the [[amino acid]] [[serine]], but it has an additional methylene group. It is classified as a [[hydroxy acid]] due to the presence of a hydroxyl group (-OH) attached to the carbon chain. The compound exists in two enantiomeric forms, D-homoserine and L-homoserine, with L-homoserine being the biologically active form.
* [[Amino acid synthesis]]
* [[Metabolic pathway]]
* [[Essential amino acid]]


==Biosynthesis==
== References ==
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 form aspartate-semialdehyde. This intermediate is subsequently converted to homoserine by the enzyme homoserine dehydrogenase.
{{Reflist}}


==Role in Metabolism==
== External Links ==
Homoserine serves as a precursor in the biosynthetic pathways of several essential amino acids:
* [https://www.wikimd.com/wiki/Homoserine Homoserine on WikiMD]
* [[Methionine]]: Homoserine is converted to O-phosphohomoserine, which is then transformed into homocysteine and subsequently methionine.
* [[Threonine]]: Homoserine is phosphorylated to form O-phosphohomoserine, which is then converted to threonine by threonine synthase.
* [[Isoleucine]]: Homoserine is involved in the biosynthesis of isoleucine through a series of reactions that also involve threonine.


==Industrial and Biotechnological Applications==
Homoserine and its derivatives are used in various industrial and biotechnological applications. It is a key intermediate in the production of amino acids and other compounds through microbial fermentation processes. Additionally, homoserine can be used as a building block in the synthesis of pharmaceuticals and other bioactive molecules.
==Related Pages==
* [[Amino acid]]
* [[Biosynthesis]]
* [[Methionine]]
* [[Threonine]]
* [[Isoleucine]]
* [[Aspartic acid]]
* [[Enzyme]]
* [[Metabolism]]
==Categories==
[[Category:Amino acids]]
[[Category:Amino acids]]
[[Category:Biochemistry]]
[[Category:Biochemistry]]
[[Category:Metabolism]]
[[Category:Metabolism]]
[[Category:Organic compounds]]
{{Amino acids}}
{{medicine-stub}}

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
Density
Melting Point
Boiling Point
Hazards
GHS Pictograms [[File:|50px]]
GHS Signal Word
GHS Hazard Statements
NFPA 704 [[File:|50px]]
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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