Isovaline: Difference between revisions

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'''Isovaline''' is a non-proteinogenic [[amino acid]] that has been found in meteorites. It is notable for its extraterrestrial origin and its potential implications for the [[origin of life]] and [[astrobiology]].
{{DISPLAYTITLE:Isovaline}}


== Structure and properties ==
== Isovaline ==
[[File:Isovaline_Isovalin.svg|thumb|right|Chemical structure of Isovaline]]
'''Isovaline''' is a non-proteinogenic [[amino acid]] with the chemical formula C<sub>5</sub>H<sub>11</sub>NO<sub>2</sub>. It is an unusual amino acid because it is not incorporated into proteins during [[translation (biology)|protein synthesis]]. Isovaline is of interest in both [[astrobiology]] and [[pharmacology]] due to its unique properties and potential applications.


Isovaline has a structure similar to the proteinogenic amino acids [[isoleucine]] and [[leucine]]. It is a [[chiral]] molecule, with two possible [[enantiomer]]s. This property is significant in the context of the origin of life, as it may provide clues about the mechanisms of [[chirality]] in biological systems.
== Structure and Properties ==
Isovaline is characterized by its [[alpha-amino acid|alpha-amino]] and [[carboxylic acid]] functional groups, similar to other amino acids. However, it has a distinctive side chain that differentiates it from the 20 standard amino acids. The presence of a [[methyl group]] in its side chain gives it a branched structure, which is a feature it shares with other [[branched-chain amino acids]] like [[valine]], [[leucine]], and [[isoleucine]].


== Occurrence ==
== Occurrence ==
Isovaline has been detected in [[meteorites]], which has sparked interest in its role in the [[origin of life]] on [[Earth]]. Its presence in extraterrestrial materials suggests that it may have been delivered to Earth via [[meteorite]] impacts, contributing to the prebiotic chemistry that led to the development of life.


Isovaline has been found in several types of meteorites, including [[carbonaceous chondrite]]s. The presence of isovaline and other amino acids in these meteorites suggests that they may have been formed in extraterrestrial environments, possibly through reactions involving [[cyanide]].
== Pharmacological Potential ==
In pharmacology, isovaline has been studied for its potential [[analgesic]] and [[anxiolytic]] effects. Unlike many other amino acids, isovaline does not readily cross the [[blood-brain barrier]], which limits its direct effects on the central nervous system. However, it has been shown to modulate [[GABA]]ergic activity, which may contribute to its calming effects.


== Significance ==
== Synthesis ==
 
The synthesis of isovaline can be achieved through various chemical methods, often involving the use of [[asymmetric synthesis]] techniques to produce the desired [[enantiomer]]. The ability to synthesize isovaline in the laboratory allows for detailed studies of its properties and potential applications.
The discovery of isovaline in meteorites has implications for the study of the origin of life and astrobiology. It supports the idea that the building blocks of life may have been delivered to Earth from space. The chiral nature of isovaline also raises questions about the origin of biological chirality, which is a fundamental characteristic of life as we know it.
 
== See also ==


== Related pages ==
* [[Amino acid]]
* [[Amino acid]]
* [[Chirality (chemistry)]]
* [[Non-proteinogenic amino acid]]
* [[Meteorite]]
* [[Meteorite]]
* [[Origin of life]]
* [[Origin of life]]
* [[Astrobiology]]
* [[Pharmacology]]


[[Category:Amino acids]]
[[Category:Amino acids]]
[[Category:Meteorites]]
[[Category:Origin of life]]
[[Category:Astrobiology]]
[[Category:Astrobiology]]
 
[[Category:Pharmacology]]
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Latest revision as of 10:56, 15 February 2025


Isovaline[edit]

Chemical structure of Isovaline

Isovaline is a non-proteinogenic amino acid with the chemical formula C5H11NO2. It is an unusual amino acid because it is not incorporated into proteins during protein synthesis. Isovaline is of interest in both astrobiology and pharmacology due to its unique properties and potential applications.

Structure and Properties[edit]

Isovaline is characterized by its alpha-amino and carboxylic acid functional groups, similar to other amino acids. However, it has a distinctive side chain that differentiates it from the 20 standard amino acids. The presence of a methyl group in its side chain gives it a branched structure, which is a feature it shares with other branched-chain amino acids like valine, leucine, and isoleucine.

Occurrence[edit]

Isovaline has been detected in meteorites, which has sparked interest in its role in the origin of life on Earth. Its presence in extraterrestrial materials suggests that it may have been delivered to Earth via meteorite impacts, contributing to the prebiotic chemistry that led to the development of life.

Pharmacological Potential[edit]

In pharmacology, isovaline has been studied for its potential analgesic and anxiolytic effects. Unlike many other amino acids, isovaline does not readily cross the blood-brain barrier, which limits its direct effects on the central nervous system. However, it has been shown to modulate GABAergic activity, which may contribute to its calming effects.

Synthesis[edit]

The synthesis of isovaline can be achieved through various chemical methods, often involving the use of asymmetric synthesis techniques to produce the desired enantiomer. The ability to synthesize isovaline in the laboratory allows for detailed studies of its properties and potential applications.

Related pages[edit]