ChemicalBook CAS DataBase List 20859-02-3

20859-02-3

Name	L-tert-Leucine
CAS	20859-02-3
EINECS(EC#)	200-522-0
Molecular Formula	C6H13NO2
MDL Number	MFCD00002617
Molecular Weight	131.17
MOL File	20859-02-3.mol

Chemical Properties

Appearance	White to almost white powder
Melting point	≥300 °C (lit.)
alpha	6.3 º (c=4, 6 N HCl 200 ºC)
Boiling point	217.7±23.0 °C(Predicted)
density	1.1720 (estimate)
refractive index	-9 ° (C=3, H2O)
storage temp.	Store at RT.
solubility	1 M HCl: 50 mg/mL
form	powder
pka	2.39±0.12(Predicted)
color	White to almost white
Optical Rotation	[α]20/D 9.5°, c = 3 in H2O
Water Solubility	125.5 g/L (20 ºC)
BRN	1721824
Major Application	peptide synthesis
InChI	1S/C6H13NO2/c1-6(2,3)4(7)5(8)9/h4H,7H2,1-3H3,(H,8,9)/t4-/m1/s1
InChIKey	NPDBDJFLKKQMCM-SCSAIBSYSA-N
SMILES	CC(C)(C)[C@H](N)C(O)=O
CAS DataBase Reference	20859-02-3(CAS DataBase Reference)

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H315-H319
Precautionary statements	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362
Hazard Codes	Xi
Safety Statements	S22:Do not breathe dust . S24/25:Avoid contact with skin and eyes . less more
WGK Germany	3
RTECS	OH2850000
Hazard Note	Irritant
REACH Registrations	Active
HS Code	29224900
Storage Class	11 - Combustible Solids

Raw materials And Preparation Products

Hazard Information

Chemical Properties

White to almost white powder

Uses

L-tert-Leucine is an essential amino acid and makes up one third of our muscle protein. It can be used as a food additive. It is used in the formation of sterols. It is used in the production of cobalt oxazoline palladacycles complex, which acts as a catalyst in the rearrangement of prochiral N-aryl trifluoroacetimidates to allylic amides yielded in significantly higher enantioselectivities with the (S)-(pR)-diasteroisomer.

Production Methods

The synthesis method of L-tert-Leucine (L-Tle) includes chemical and biological methods. Compared with traditional chemical synthesis, the enzymatic reduction of chiral keto acid to synthesize the corresponding unnatural amino acid has the advantages of high optical purity, mild reaction conditions, high conversion rate, and environmental friendliness. Currently, enzymatic methods have gradually replaced chemical methods. Some previous research on preparing L-tert-leucine using hydrolase, acyltransferase, and amino acid dehydrogenase has been reported. Among them, the preparation of L-tert-leucine using NADH-dependent L-leucine dehydrogenase (LeuDH, EC 1.4.1.9) has exhibited the most industrial potential. In the presence of NADH and free ammonium, LeuDH can catalyze trimethylpyruvate (TMP) to L-tert-leucine[1-3].

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 3, p. 523, 1955
Tetrahedron Letters, 19, p. 4625, 1978 DOI: 10.1016/S0040-4039(01)85688-4

General Description

L-tert-Leucine (L-Tle) is an essential non-natural amino acid often used as a template to induce asymmetric synthesis, and the product has high stereoselectivity. It is a non-polar amino acid, and its tert-butyl group has significant hydrophobicity and steric hindrance, which can control molecular conformation in a chemical reaction and form a chiral compound. Hence, L-tert-leucine is commonly used as an inducer or a template in asymmetric synthesis. As a vital chiral intermediate, L-tert-leucine is widely used to synthesise anti-cancer, anti-viral, and biological inhibitors. In addition, L-tert-leucine is an essential additive in the food and cosmetic industry[1].

reaction suitability

reaction type: solution phase peptide synthesis

Questions And Answer

Spectrum Detail

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20859-02-3

Chemical Properties

Safety Data

Raw materials And Preparation Products

Raw materials

Preparation Products

Hazard Information

Chemical Properties

Uses

Production Methods

Synthesis Reference(s)

General Description

reaction suitability

Questions And Answer

Description

References

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

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