Synonyms:L-pipecolate;(S)-pipecolate;L-pipecolic acid zwitterion;CHEBI:61185;(2S)-piperidinium-2-carboxylate;dl-homoproline, dl-pipecolic acid;(S)-2-carboxypiperidinium betaine
98% Min *data from raw suppliers
L-Pipecolic acid *data from reagent suppliers
Xi
There total 99 articles about L-pipecolate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
Reference yield: 45.0%
Reference yield: 9.0%
Reference yield:
The research focuses on the straightforward synthesis of novel chiral ligands, [(2S,4R)-1-cyclohexyl-4-methylpiperidin-2-yl]methanol (5a) and (2S,4R)-1-cyclohexyl-4-methylpiperidin-2-ylmethanol (5b), derived from L-pipecolinic acid (homoproline). The purpose of this study was to develop new β-amino alcohols that could serve as chiral ligands for the catalytic addition of diethylzinc to benzaldehyde, with the aim of achieving high enantioselectivity in the process. The researchers found that these ligands exhibited unique behavior in stereocontrol compared to other C(4)-unsubstituted analogues. The study concluded that the enantioselective addition of diethylzinc to benzaldehyde, mediated by ligands 5a and 5c, showed a dependence on the combination of substituents on the structural scaffold and the metal-alkoxide involved in the catalysis, such as zinc or lithium alkoxides. Theoretical DFT methods were also employed to evaluate the stereoselectivity of the reaction, providing insights into the role of different catalyst loadings in the reaction medium. Key chemicals used in the synthesis process included rac-alaninol, rac-2-amino-1,1-diphenylpropan-1-ol, and various reagents for the preparation of the ligands and the subsequent catalytic reactions, such as diethylzinc, benzaldehyde, and metal alkoxides.
The research presents an in-depth study on the biosynthesis of pipecolic acid by RapL, a lysine cyclodeaminase enzyme encoded in the rapamycin gene cluster. The main focus of the study is to validate RapL's ability to convert L-lysine to L-pipecolic acid through a cyclodeamination reaction involving redox catalysis. The researchers heterologously overexpressed and purified RapL, and conducted a series of experiments to confirm its enzymatic activity. They used L-lysine and L-[U-14C]ornithine as substrates, NAD+ as a cofactor, and analyzed the reactions using techniques such as cellulose thin layer chromatography (TLC), chiral radio-HPLC, and mass spectrometry. The study also investigated the enzyme's substrate specificity, cofactor requirements, and inhibitory properties. Additionally, the researchers used isotopically labeled substrates to dissect the mechanistic details of the cyclodeaminase reaction, confirming the loss of the R-amine and retention of the hydrogen atom at the R-carbon. The experiments provided the first in vitro characterization of a lysine cyclodeaminase and contributed to the understanding of the biosynthesis of medically important natural products like rapamycin, FK506, and FK520.
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