Norleucine: Difference between revisions

Latest revision as of 03:50, 13 February 2025

Norleucine[edit]

Norleucine is a non-proteinogenic amino acid with the chemical formula C_H__NO_. It is an isomer of the amino acid leucine, differing by the position of the methyl group. Norleucine is not incorporated into proteins during translation but is used in various biochemical studies and industrial applications.

Structure and Properties[edit]

Norleucine is a straight-chain amino acid, which means it has a linear aliphatic side chain. The structure of norleucine is similar to that of leucine, but with the methyl group located at the end of the chain rather than on the second carbon. This gives norleucine the systematic name 2-aminohexanoic acid.

The presence of the amino group (NH_) and the carboxyl group (COOH) makes norleucine an amphoteric compound, capable of acting as both an acid and a base. It is a white crystalline solid at room temperature and is soluble in water.

Biological Role[edit]

Norleucine is not one of the 20 standard amino acids encoded by the genetic code. However, it is often used in biochemistry as a standard for chromatography and as an internal standard in mass spectrometry.

In some organisms, norleucine can be incorporated into proteins in place of methionine, especially under conditions where methionine is scarce. This substitution can affect the function and stability of the protein.

Industrial and Research Applications[edit]

Norleucine is used in the synthesis of peptides and as a precursor in the production of various pharmaceuticals. It is also employed in the study of enzyme mechanisms and protein structure.

In research, norleucine is used as a tool to investigate the ribosome's ability to discriminate between different amino acids during protein synthesis. It is also used in studies of protein folding and stability.

Related Compounds[edit]

Related Pages[edit]

@@ Line 1: / Line 1: @@
-{{Short description|An amino acid used in scientific research}}
+{{DISPLAYTITLE:Norleucine}}
-{{Infobox amino acid
-| name = Norleucine
-| image = Norleucine.png
-| image_size = 200px
-| IUPAC_name = 2-Aminohexanoic acid
-| other_names = 2-Aminocaproic acid
-| abbreviation = Nle
-| formula = C<sub>6</sub>H<sub>13</sub>NO<sub>2</sub>
-| molar_mass = 131.18 g/mol
-| CAS_number = 327-57-1
-}}
-'''Norleucine''' is a non-proteinogenic [[amino acid]] with the chemical formula C<sub>6</sub>H<sub>13</sub>NO<sub>2</sub>. It is an isomer of the essential amino acid [[leucine]], differing by the position of the amino group. Norleucine is not incorporated into proteins during [[translation (biology)|protein synthesis]] in living organisms, but it is often used in scientific research as a model compound.
+== Norleucine ==
+[[File:L-Norleucin.svg|thumb|right|Structural formula of L-Norleucine]]
+'''Norleucine''' is a non-proteinogenic [[amino acid]] with the chemical formula C_H__NO_. It is an isomer of the amino acid [[leucine]], differing by the position of the methyl group. Norleucine is not incorporated into proteins during [[translation (biology)|translation]] but is used in various biochemical studies and industrial applications.
-==Structure and Properties==
+== Structure and Properties ==
-Norleucine is a straight-chain amino acid, classified as a non-polar, aliphatic amino acid. Its structure consists of a six-carbon chain with an amino group (NH<sub>2</sub>) at the second carbon and a carboxyl group (COOH) at the terminal carbon. This structure is similar to that of leucine, but with a linear rather than branched side chain.
+Norleucine is a straight-chain amino acid, which means it has a linear aliphatic side chain. The structure of norleucine is similar to that of leucine, but with the methyl group located at the end of the chain rather than on the second carbon. This gives norleucine the systematic name 2-aminohexanoic acid.
-==Synthesis==
+The presence of the amino group (NH_) and the carboxyl group (COOH) makes norleucine an [[amphoteric]] compound, capable of acting as both an acid and a base. It is a white crystalline solid at room temperature and is soluble in water.
-Norleucine can be synthesized through various chemical methods. One common method involves the hydrogenation of α-keto acids or the reductive amination of aldehydes. These synthetic routes allow for the production of norleucine in the laboratory for research purposes.
-==Applications in Research==
+== Biological Role ==
-Norleucine is frequently used in [[biochemistry]] and [[molecular biology]] as a standard or reference compound. It is often employed in studies of protein structure and function, particularly in [[mass spectrometry]] and [[chromatography]] techniques. Norleucine can serve as an internal standard in [[amino acid analysis]] due to its absence in natural proteins, allowing for accurate quantification of other amino acids.
+Norleucine is not one of the 20 standard amino acids encoded by the [[genetic code]]. However, it is often used in [[biochemistry]] as a standard for [[chromatography]] and as an internal standard in [[mass spectrometry]].
-==Biological Significance==
+In some organisms, norleucine can be incorporated into proteins in place of methionine, especially under conditions where methionine is scarce. This substitution can affect the function and stability of the protein.
-Although norleucine is not found in natural proteins, it can be incorporated into proteins in vitro using [[genetic code expansion]] techniques. This allows researchers to study the effects of non-canonical amino acids on protein structure and function. Norleucine's incorporation can provide insights into the flexibility and adaptability of the [[ribosome]] and the [[genetic code]].
-==Safety and Handling==
+== Industrial and Research Applications ==
-As with many chemical compounds, proper safety precautions should be taken when handling norleucine. It should be stored in a cool, dry place and handled with appropriate personal protective equipment to avoid ingestion, inhalation, or skin contact.
+Norleucine is used in the synthesis of [[peptides]] and as a precursor in the production of various [[pharmaceuticals]]. It is also employed in the study of [[enzyme]] mechanisms and protein structure.
-==Also see==
+In research, norleucine is used as a tool to investigate the [[ribosome]]'s ability to discriminate between different amino acids during protein synthesis. It is also used in studies of [[protein folding]] and stability.
+== Related Compounds ==
 * [[Leucine]]
+* [[Isoleucine]]
+* [[Methionine]]
+== Related Pages ==
 * [[Amino acid]]
 * [[Protein synthesis]]
-* [[Genetic code expansion]]
+* [[Biochemistry]]
-* [[Mass spectrometry]]
-{{Amino acids}}
 [[Category:Amino acids]]
-[[Category:Biochemistry]]
-[[Category:Research methods]]