L-Alaninol

L-Alaninol ((S)-2-Amino-1-propanol; (S)-2-Aminopropanol; (S)-Alaninol) is a chiral amino alcohol that serves as a precursor for Levofloxacin (HY-B0330) and Metolachlor (HY-B1871). L-Alaninol acts as the sole carbon source for Pseudomonas sp. strain KIE171, and it is a metabolite produced by the hydrolysis of γ-glutamyl-L-alaninol. L-Alaninol functions as a substrate for oxidative/deaminative degradation and undergoes enzymatic glutamylation via IpuC. It is used as a synthetic building block in the fields of agriculture, pharmaceuticals, and peptide chemistry, and also serves as a chiral auxiliary^[1][2][3]. In Vitro:L-Alaninol is a precursor of Levofloxacin (HY-B0330) and Metolachlor (HY-B1871)^[1].
L-alaninol is produced by Pseudomonas sp. KIE171 using IPA as a substrate via sequential glutamylation, hydroxylation and hydrolysis reactions, and the generated L-alaninol can undergo further oxidation or deamination reactions^[1].
L-Alaninol serves as the sole carbon source for Pseudomonas sp. strain KIE171, while the mutant strain KIE171-B converts isopropylamine to L-alaninol within 40 h without producing D-alaninol^[2].
L-Alaninol (10 mM) undergoes ATP-dependent glutamylation catalyzed by purified γ-glutamine synthetase derived from recombinant E. coli; it can also be released via the hydrolysis of γ-glutamyl-L-alaninol by purified γ-glutamine amidohydrolase, with a V_max of 1.5 U/mg of protein^[2].
L-Alaninol (0.22 M; 1-6 h) undergoes stereoretentive deuteration at the C1 and C2 positions with minimal loss of enantiomeric excess under the condition of 100 °C (with or without acid addition). L-Alaninol (0.22 M; 6 h) triggers racemization, reduces enantiomeric excess to 60.5%, and elevates the deuteration degree at the C3 position when incubated at 150 °C without acid addition^[3].