ChemicalBook CAS DataBase List L(-)-Pipecolinic acid

L(-)-Pipecolinic acid synthesis

9synthesis methods

Product Name:L(-)-Pipecolinic acid
CAS Number:3105-95-1
Molecular formula:C6H11NO2
Molecular Weight:129.16

L(-)-Pipecolinic acid is a normal metabolite present in human blood. It can be synthesized from the palladium-carbon catalyzed hydrogenation reduction reaction of N-Cbz-L-pipecolic acid in methanol.

56-87-1 Synthesis

56-87-1
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3105-95-1
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1723-00-8
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Yield:86 % ee

Reaction Conditions:

with Cp*Ir(biot-p-L)Cl;D-amino acidoxidase from porcine kidney;L-amino acid oxidase from Crotalus atrox;streptavidin S₁₁₂A mutant;oxygen;sodium formate;catalase from bovine liver in aq. buffer at 37; pH=7.8;Enzymatic reaction;enantioselective reaction;Reagent/catalyst;

Steps:

Typical procedure for a double stereoselective deracemization with MAON/ATHase (analytical scale).

General procedure: The following stock solutions were prepared. Catalase from bovine liver (50 kU ml^-1) was dissolved in MOPS/sodium formate buffer (0.6 M in MOPS, 3.0 M in sodium formate, pH adjusted with aq. KOH to pH 7.8). Sav S112T (16.4 mg ml^-1, 0.75 mM free binding sites, assuming three free binding sites per tetramer) was dissolved in the catalase containing buffer. [IrCp*(biot-p-L)Cl] was dissolved in DMF (37.5 mM). Affinity purified MAO-N-9 (buffer exchange with MOPS, 0.6 M, pH adjusted with KOH to 7.8) was diluted in MOPS buffer (0.6 M, pH adjusted with KOH to 7.8) to a concentration of 0.38 mg ml^-1. Substrate stock was prepared by dissolving the hydrochloride of 1-ox in H₂O (1 M). The ATHase was prepared by adding [IrCp*(biot-p-L)Cl]-stock (10 μl ml^-1) to the Sav-stock solution. MAO-N-stock was placed in 1.5 ml PP-tubes (100 μl) and ATHase was added (100 μl). The reactions were initiated by addition of substrate stock solution (7.5 μl) and incubated at 37 °C and 250 r.p.m. in a lying position. For work-up aq. NaOH solution was added (50 μl of a 10 M solution) and the mixture extracted with CH₂Cl₂ (1 × 1 ml). The organic phase was dried over Na₂SO₄ and analysed by HPLC (Supplementary Sections S2.3.1 and S2.4.1).

References:

Koehler;Wilson;Duerrenberger;Ghislieri;Churakova;Quinto;Knoerr;Haeussinger;Hollmann;Turner;Ward [Nature Chemistry,2013,vol. 5,# 2,p. 93 - 99]

28697-11-2 Synthesis