Chemical Properties
Colorless liquid
Uses
(
S)-(+)-2-Amino-1-propanol (L-Alaninol) may be used in the preparation of unsymmetrical tridentate Schiff base ligands via condensation with carbonyl compounds. It may also be used as a chiral auxillary for the preparation of
tert-butyl 4-
N-[(2-hydroxy-1-(
S)-methyl)ethylamino]-2-methylene-4-(
S)-phenyl-butyrate.
Uses
S-(+)-2-Amino-1-propanol is an aliphatic amino alcohol shown to induce an antiproliferative effect in B16 melanoma cells. S-(+)-2-Amino-1-propanol is used in the preparation of oxazolines which are of
ten used as ligands in homogeneous catalysis.
Definition
ChEBI: An amino alcohol that is L-alanine in which the carboxy group has been reduced to the corresponding alcohol.
Biochem/physiol Actions
Pseudomonas sp. strain KIE171 was able to grow with L-alaninol [S-(+)-2-amino-1-propanol] as the sole carbon source[1]. W?sch et al. found that mutant KIE171-BI transformed isopropylamine to L-alaninol, mutant KIE171-BII failed to do so.
Synthesis
Simply produce L-alaninol in high yield and good reproducibility by directly reducing an inorganic acid salt of an L-alanine ester with NaBH4. 3.0 mol of NaBH 4 was added and dissolved in 560 ml of cold water, and L-alanine ethyl ester hydrochloride 1. A solution of 0 mol dissolved in 560 ml of ethanol was added. The mixture was added dropwise at 20 ° C. over 5 hours and further aged at 20 to 28 ° C. to complete the reaction. After the reaction, excess NaBH 4 was decomposed with acetone, 1000 ml of ethyl acetate was introduced, and the precipitated inorganic substance was separated by filtration. The lower aqueous layer portion of the filtrate was extracted with 600 ml of ethyl acetate; the ethyl acetate layer was distilled under reduced pressure to remove the solvent and then vacuum distilled to yield L-alaninol.
Purification Methods
Purify it as for S-2-amino-3-methylbutan-1-ol below. [Beilstein 4 IV 1615.]
References
[1] Susana I de Azevedo W?sch. “Transformation of isopropylamine to L-alaninol by Pseudomonas sp. strain KIE171 involves N-glutamylated intermediates.”Applied and Environmental Microbiology (2002): 68.
