Isovaline
Structural formula | |||||||||||||
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( S ) -Isovaline is shown | |||||||||||||
General | |||||||||||||
Surname | Isovaline | ||||||||||||
other names |
Ethyl methyl glycine |
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Molecular formula | C 5 H 11 NO 2 | ||||||||||||
External identifiers / databases | |||||||||||||
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properties | |||||||||||||
Molar mass | 117.15 g · mol -1 | ||||||||||||
Physical state |
firmly |
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solubility |
easily soluble in water |
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safety instructions | |||||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Isovaline (also called Iva for short) is a rare α- amino acid that was found in meteorites (e.g. in the Murchison meteorite ).
Isomerism
Isovaline occurs in the two enantiomeric forms L -isovaline [synonym: ( S ) -isovaline] and D -isovaline [synonym: ( R ) -isovalin] and, in its left-handed form, is a good catalyst to generate right-handed sugar molecules.
Isomers of isovaline | ||
Surname | L -isovaline | D -isovaline |
other names | ( S ) -Isovaline | ( R ) -Isovaline |
Structural formula | ![]() |
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CAS number | 595-40-4 | 3059-97-0 |
595-39-1 (unspec.) | ||
PubChem | 6971275 | 2724877 |
- (unspec.) | ||
DrugBank | - | DB04171 |
- (unspec.) | ||
Wikidata | Q29625345 | Q27095005 |
Q412994 (unspec.) |
Structurally, isovaline is derived from 2-methylbutyric acid by substituting the α- hydrogen atom with an amino group (-NH 2 ) . Valine and norvaline are constitutional isomers .
Individual evidence
- ↑ a b c Data sheet D -Isovalin from Acros, accessed on June 21, 2019.
- ↑ Keith A. Kvenvolden, James G. Lawless, Cyril Ponnamperuma: Nonprotein Amino Acids in the Murchison Meteorite , in: Proc. Natl. Acad. Sci. USA , 1971 , 68 (2), pp. 486-490; PMID 16591908 ; PMC 388966 (free full text, PDF).
- ↑ Sandra Pizzarello, Arthur L. Weber: Prebiotic amino acids as asymmetric catalysts , in: Science , 2004 , 303 (5661), p. 1151; PMID 14976304 .