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| ImageFileR1 = L-Norvalin.svg
| ImageFileR1 = L-Norvalin.svg
| IUPACName=2-Aminopentanoic acid
| IUPACName=2-Aminopentanoic acid
| OtherNames=2-Aminopentyric acid; α-Aminopentanoic acid; Propylglycine
| OtherNames=2-Aminovaleric acid; α-Aminopentanoic acid; Propylglycine
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo = 6600-40-4
| CASNo = 6600-40-4
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = A70UKS48FE
| ChemSpiderID = 58608
| ChemSpiderID = 58608
| ChemSpiderID_Comment = (<small>L</small>)
| ChemSpiderID_Comment = (<small>L</small>)
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}}
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'''Norvaline''' (abbreviated as '''Nva''') is an [[amino acid]] with the formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>2</sub>CH(NH<sub>2</sub>)CO<sub>2</sub>H. The compound is an isomer of the more common amino acid [[valine]].<ref>[http://www.merriam-webster.com/medical/norvaline Merriam-Webster] Retrieved 4 September 2010</ref> Like most other [[α-amino acid]]s, norvaline is [[chiral]]. It is a white, water-soluble solid.
'''Norvaline''' (abbreviated as '''Nva''') is an [[amino acid]] with the formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>2</sub>CH(NH<sub>2</sub>)CO<sub>2</sub>H. The compound is a [[structural analog]] of [[valeric acid]] and also an [[isomer]] of the more common amino acid [[valine]].<ref>[http://www.merriam-webster.com/medical/norvaline Merriam-Webster] Retrieved 4 September 2010</ref> Like most other [[α-amino acid]]s, norvaline is [[chiral]]. It is a white, water-soluble solid.


==Occurrence==
==Occurrence==
Norvaline is a [[Non-proteinogenic amino acids|non-proteinogenic]] unbranched-chain amino acid. It has previously been reported to be a natural component of an antifungal peptide of ''[[Bacillus subtilis]]''. Norvaline and other modified unbranched chain amino acids have received attention because they appear to be incorporated in some recombinant proteins found in ''[[E. coli]]''.<ref>{{cite journal |vauthors=Soini J, Falschlehner C, Liedert C, Bernhardt J, Vuoristo J, Neubauer P |title=Norvaline is accumulated after a down-shift of oxygen in Escherichia coli W3110 |journal=Microbial Cell Factories |volume=7 |issue= |pages=30 |year=2008 |pmid=18940002 |pmc=2579280 |doi=10.1186/1475-2859-7-30}}</ref> Its [[biosynthesis]] has been examined. The incorporation of Nva into peptides reflects the imperfect selectivity of the associated [[aminoacyl-tRNA synthetase]]. In [[Miller–Urey experiment]]s probing prebiotic synthesis of amino acids, norvaline, but also [[norleucine]], are produced.<ref>{{cite journal |vauthors=Alvarez-Carreño C, Becerra A, Lazcano A |title=Norvaline and norleucine may have been more abundant protein components during early stages of cell evolution |journal=Origins of Life and Evolution of the Biosphere |volume=43 |issue=4-5 |pages=363–75 | date=October 2013 |pmid=24013929 |doi=10.1007/s11084-013-9344-3}}</ref>
Norvaline is a [[Non-proteinogenic amino acids|non-proteinogenic]] unbranched-chain amino acid. It has previously been reported to be a natural component of an antifungal peptide of ''[[Bacillus subtilis]]''. Norvaline and other modified unbranched chain amino acids have received attention because they appear to be incorporated in some recombinant proteins found in ''[[E. coli]]''.<ref>{{cite journal |vauthors=Soini J, Falschlehner C, Liedert C, Bernhardt J, Vuoristo J, Neubauer P |title=Norvaline is accumulated after a down-shift of oxygen in Escherichia coli W3110 |journal=Microbial Cell Factories |volume=7 |pages=30 |year=2008 |pmid=18940002 |pmc=2579280 |doi=10.1186/1475-2859-7-30 |doi-access=free }}</ref> Its [[biosynthesis]] has been examined. The incorporation of Nva into peptides reflects the imperfect selectivity of the associated [[aminoacyl-tRNA synthetase]]. In [[Miller–Urey experiment]]s probing prebiotic synthesis of amino acids, norvaline, but also [[norleucine]], are produced.<ref>{{cite journal |vauthors=Alvarez-Carreño C, Becerra A, Lazcano A |title=Norvaline and norleucine may have been more abundant protein components during early stages of cell evolution |journal=Origins of Life and Evolution of the Biosphere |volume=43 |issue=4–5 |pages=363–75 | date=October 2013 |pmid=24013929 |doi=10.1007/s11084-013-9344-3|bibcode=2013OLEB...43..363A |s2cid=17224537 }}</ref>

Norvaline is known to promote [[tissue regeneration]] and [[muscle growth]],<ref>{{cite journal |vauthors=Ming XF, Rajapakse AG, Carvas JM, Ruffieux J, Yang Z |title=Inhibition of S6K1 accounts partially for the anti-inflammatory effects of the arginase inhibitor L-norvaline |journal=BMC Cardiovascular Disorders |volume=9 |issue= |pages=12 |year=2009 |pmid=19284655 |pmc=2664787 |doi=10.1186/1471-2261-9-12}}</ref> and to become a precursor in the penicillin biosynthetic pathway.<ref>[http://www.reference.md/files/C005/mC005313.html reference.md] Retrieved 4 September 2010{{full citation needed|date=January 2015}}</ref><ref>{{cite journal |vauthors=Kisumi M, Sugiura M, Chibata I |title=Biosynthesis of norvaline, norleucine, and homoisoleucine in Serratia marcescens |journal=Journal of Biochemistry |volume=80 |issue=2 |pages=333–9 | date=August 1976 |pmid=794063 |url=http://jb.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=794063}}</ref>


==Nomenclature==
==Nomenclature==
Norvaline and [[norleucine]] (one hydrocarbon group longer) both possess the [[Nor-|nor- prefix]] for historical reason, despite current conventional usage of the prefix to denote a missing hydrocarbon group (under which they would theoretically be called "dihomoalanine" and "trihomoalanine"). The name is not systematic.<ref>{{cite journal | title = Nomenclature and Symbolism For Amino Acids and Peptides | journal = Pure and Applied Chemistry | volume = 56 | issue = 5 | pages = 595–624 | date = 1984|doi=10.1351/pac198456050595 }}</ref>
Norvaline and [[norleucine]] (one hydrocarbon group longer) both possess the [[Nor-|nor- prefix]] for historical reason, despite current conventional usage of the prefix to denote a missing hydrocarbon group (under which they would theoretically be called "dihomoalanine" and "trihomoalanine"). The name is not systematic, and the IUPAC/IUB Joint Commission on Nomenclature recommends that this name should be abandoned and the systematic name should be used.<ref>{{cite journal | title = Nomenclature and Symbolism For Amino Acids and Peptides | journal = Pure and Applied Chemistry | volume = 56 | issue = 5 | pages = 595–624 | date = 1984|doi=10.1351/pac198456050595 | doi-access = free }}</ref>

==Potential uses==
Norvaline is used as a dietary supplement for bodybuilding.
Recently, it was suggested in the treatment of [[Alzheimer's disease]].<ref>Polis, B., Srikanth, K. D., Gurevich, V., Gil-Henn, H., & Samson, A. O. (2019). L-Norvaline, a new therapeutic agent against Alzheimer’s disease. Neural regeneration research, 14(9), 1562.</ref>


==References==
==References==
{{reflist}}
{{reflist}}


{{Non-proteinogenic amino acids}}

[[Category:Alpha-Amino acids]]
[[Category:Biochemistry]]
[[Category:Biochemistry]]
[[Category:Non-proteinogenic amino acids]]
[[Category:Non-proteinogenic amino acids]]

Latest revision as of 01:52, 11 October 2024

Norvaline
Names
IUPAC name
2-Aminopentanoic acid
Other names
2-Aminovaleric acid; α-Aminopentanoic acid; Propylglycine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.026.858 Edit this at Wikidata
UNII
  • (L): InChI=1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
    Key: SNDPXSYFESPGGJ-BYPYZUCNSA-N
  • (DL): InChI=1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)
    Key: SNDPXSYFESPGGJ-UHFFFAOYSA-N
  • (D): InChI=1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m1/s1
    Key: SNDPXSYFESPGGJ-SCSAIBSYSA-N
  • (L): CCC[C@@H](C(=O)O)N
  • (DL): CCCC(C(=O)O)N
  • (D): CCC[C@H](C(=O)O)N
Properties
C5H11NO2
Molar mass 117.148 g·mol−1
Acidity (pKa) 2.36 (carboxyl), 9.76 (amino)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Norvaline (abbreviated as Nva) is an amino acid with the formula CH3(CH2)2CH(NH2)CO2H. The compound is a structural analog of valeric acid and also an isomer of the more common amino acid valine.[2] Like most other α-amino acids, norvaline is chiral. It is a white, water-soluble solid.

Occurrence

[edit]

Norvaline is a non-proteinogenic unbranched-chain amino acid. It has previously been reported to be a natural component of an antifungal peptide of Bacillus subtilis. Norvaline and other modified unbranched chain amino acids have received attention because they appear to be incorporated in some recombinant proteins found in E. coli.[3] Its biosynthesis has been examined. The incorporation of Nva into peptides reflects the imperfect selectivity of the associated aminoacyl-tRNA synthetase. In Miller–Urey experiments probing prebiotic synthesis of amino acids, norvaline, but also norleucine, are produced.[4]

Nomenclature

[edit]

Norvaline and norleucine (one hydrocarbon group longer) both possess the nor- prefix for historical reason, despite current conventional usage of the prefix to denote a missing hydrocarbon group (under which they would theoretically be called "dihomoalanine" and "trihomoalanine"). The name is not systematic, and the IUPAC/IUB Joint Commission on Nomenclature recommends that this name should be abandoned and the systematic name should be used.[5]

Potential uses

[edit]

Norvaline is used as a dietary supplement for bodybuilding. Recently, it was suggested in the treatment of Alzheimer's disease.[6]

References

[edit]
  1. ^ Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.[page needed]
  2. ^ Merriam-Webster Retrieved 4 September 2010
  3. ^ Soini J, Falschlehner C, Liedert C, Bernhardt J, Vuoristo J, Neubauer P (2008). "Norvaline is accumulated after a down-shift of oxygen in Escherichia coli W3110". Microbial Cell Factories. 7: 30. doi:10.1186/1475-2859-7-30. PMC 2579280. PMID 18940002.
  4. ^ Alvarez-Carreño C, Becerra A, Lazcano A (October 2013). "Norvaline and norleucine may have been more abundant protein components during early stages of cell evolution". Origins of Life and Evolution of the Biosphere. 43 (4–5): 363–75. Bibcode:2013OLEB...43..363A. doi:10.1007/s11084-013-9344-3. PMID 24013929. S2CID 17224537.
  5. ^ "Nomenclature and Symbolism For Amino Acids and Peptides". Pure and Applied Chemistry. 56 (5): 595–624. 1984. doi:10.1351/pac198456050595.
  6. ^ Polis, B., Srikanth, K. D., Gurevich, V., Gil-Henn, H., & Samson, A. O. (2019). L-Norvaline, a new therapeutic agent against Alzheimer’s disease. Neural regeneration research, 14(9), 1562.
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