tert -leucine

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Structural formula
Structure of tert-leucine
L - tert -Leucine (left) or D - tert -Leucine (right)
General
Surname tert -leucine
other names
  • ( S ) - (+) - 2-Amino-3,3-dimethylbutanoic acid
  • L - (+) - α-amino-3,3-dimethylbutanoic acid
  • ( S ) - (+) - tert -leucine
  • ( R ) - (-) - tert -leucine
  • D - (-) - α-Amino-3,3-dimethylbutanoic acid
  • Terleucine
  • 2-adba
  • 3-methylvaline
  • tert -butylglycine
Molecular formula C 6 H 13 NO 2
External identifiers / databases
CAS number
  • 20859-02-3 ( L -enantiomer)
  • 26782-71-8 ( D -enantiomer)
EC number 606-659-6
ECHA InfoCard 100.109.056
PubChem 164608
ChemSpider 144305
Wikidata Q2405866
properties
Molar mass 131.18 g mol −1
Physical state

firmly

Melting point

> 300 ° C (decomposition)

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 .

tert -Leucine (Terleucine) is a chiral , non- proteinogenic α- amino acid , of which the two enantiomers L - tert -Leucine [Synonym: ( S ) - tert -Leucine] and D - tert -Leucine [Synonym: ( R ) - tert -Leucine] exist. Structurally, tert- leucinecan bederivedfrom 3,3-dimethylbutyric acid via the substitution of an α- hydrogen atom by an amino group  (-NH 2 ). tert -leucine belongs together with its structural isomers of leucine , isoleucine and norleucine for the substance group of Leucine .

Occurrence

tert -Leucine occurs naturally as a component of the peptide antibiotic bottromycin A , which is produced by the soil bacterium Streptomyces bottropensis . It is also a component of some antimicrobial marine sponges .

presentation

L - tert - leucine is currently being produced on an enzymatic scale on a ton scale and is intended to be used as a chiral intermediate in the synthesis of drugs for the treatment of cancer or AIDS .

Individual evidence

  1. a b L-tert-Leucine data sheet from Sigma-Aldrich , accessed on May 29, 2011 ( PDF ).
  2. D. Schipper: The revised structure of bottromycin A2. In: Journal of Antibiotics . Volume 36, No. 8, August 1983, pp. 1076-1077, PMID 6630058 .
  3. N. Fusetani, S. Matsunaga: Bioactive sponge peptides. In: Chemical Reviews . Volume 93, 1993, pp. 1793-1806, doi: 10.1021 / cr00021a007 .
  4. Lutz Krieg: Screening and characterization of new amino acid amidases for racemate resolution - cloning and expression of a D-amidase from Variovorax paradoxus in E. coli. Dissertation, Heinrich Heine University Düsseldorf, 2002, p. 6, urn : nbn: de: hbz: 061-20030609-000528-2 ( PDF ).
  5. Page no longer available , search in web archives: Information from the manufacturer Degussa.  ( Page no longer available , search in web archivesInfo: The link was automatically marked as defective. Please check the link according to the instructions and then remove this notice.@1@ 2Template: Toter Link / www.degussa.de@1@ 2Template: Toter Link / www.degussa.de