Isovaline

Structural formula
( S ) -Isovaline is shown
General
Surname	Isovaline
other names	Ethyl methyl glycine
Molecular formula	C 5 H 11 NO 2
External identifiers / databases
CAS number 595-39-1 ( DL -isovaline) PubChem 94744 ChemSpider 85483 Wikidata Q412994
properties
Molar mass	117.15 g · mol -1
Physical state	firmly
solubility	easily soluble in water
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
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
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

1. ↑ ^{a b c} Data sheet D -Isovalin from Acros, accessed on June 21, 2019.
2. ↑ 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).
3. ↑ Sandra Pizzarello, Arthur L. Weber: Prebiotic amino acids as asymmetric catalysts , in: Science , 2004 , 303  (5661), p. 1151; PMID 14976304 .