Norleucine

Structural formula
Structural formula of norleucine without specifying the stereochemistry
General
Surname	Norleucine
other names	2-aminohexanoic acid α-aminocaproic acid
Molecular formula	C 6 H 13 NO 2
Brief description	colorless leaflets
External identifiers / databases
CAS number 616-06-8 EC number 210-462-7 ECHA InfoCard 100.009.512 PubChem 9475 ChemSpider 9103 Wikidata Q27116817
properties
Molar mass	131.18 g mol −1
Physical state	firmly
Melting point	301 ° C (decomposition)
solubility	poor in water (16 g l −1 at 23 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 317 P: 280
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Norleucine is a non-proteinogenic chiral α- amino acid and was first isolated by Arthur Weil .

Isomerism

There are two enantiomers of norleucine: L- norleucine [synonym: ( S ) -norleucine] and D -norleucine [synonym: ( R ) -norleucine]. Structurally, norleucine derived by substitution of a α- hydrogen atom by an amino group  (-NH ₂ ) from the caproic from. Norleucine belongs together with its structural isomers of leucine , isoleucine and tert -leucine to the substance group of Leucine .

Isomers of norleucine
Surname	L -norleucine	D -norleucine
other names	( S ) -Norleucine (+) - norleucine	( R ) -Norleucine (-) - Norleucine
Structural formula
CAS number	327-57-1	327-56-0
	616-06-8 (racemate)
EC number	206-321-4	206-320-9
	210-462-7 (racemate)
ECHA info card	100.005.748	100.005.747
	100.009.512 (racemate)
PubChem	21236	456468
	9475 (racemate)
DrugBank	-	DB04419
	- (racemate)
Wikidata	Q415428	Q27459594
	Q27116817 (racemate)

presentation

The racemate is obtained by reacting 2-bromohexanoic acid with NH ₃ in aqueous solution (50 ° C., 30 h).

use

Norleucine is used for the experimental study of protein structures and functions. Aminoacyl-tRNA synthetases can be fooled by offering them certain non-biological amino acids in place of their normal substrates. Thus ethionine and norleucine incorporated into such positions in proteins that normally methionine would take.

Individual evidence

1. ↑ ^{a b} entry on norleucine. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.
2. ↑ Data sheet L (+) - Norleucine at Acros, accessed on June 30, 2019.
3. ↑ ^{a b} L-Norleucine data sheet from Sigma-Aldrich , accessed on October 22, 2016 ( PDF ).
4. ^ Emil Abderhalden, C. Froehlich, Dionys Fuchs: cleavage of dl-aminocaproic acid (= norleucine) into the optically active components by means of the formyi compound. Polypeptides that are built with aminocaproic acid. In: Hoppe-Seyler's journal for physiological chemistry. 86, 1913, pp. 454-468, doi : 10.1515 / bchm2.1913.86.6.454 .
5. ^ K. Peter C. Vollhardt , Neil E. Schore: Organische Chemie , 4th edition, Wiley-VCH, Weinheim 2005, ISBN 978-3-527-31380-8 , p. 997.
6. ^ Albert L. Lehninger : Biochemie , 2nd edition, VCH, Weinheim 1983, ISBN 3-527-25688-1 , pp. 767-768.