3105-95-1Relevant articles and documents
One-Step Synthesis of L-Piperidine-2-carboxylic Acid
Kisfaludy, Lajos,Korenczki, Ferenc,Katho, Agnes
, p. 163 (1982)
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Enzymatic synthesis of L-pipecolic acid by Δ1-piperideine- 2-carboxylate reductase from Pseudomonas putida
Muramatsu, Hisashi,Mihara, Hisaaki,Yasuda, Mari,Ueda, Makoto,Kurihara, Tatsuo,Esaki, Nobuyoshi
, p. 2296 - 2298 (2006)
L-Pipecolic acid is a chiral pharmaceutical intermediate. An enzymatic system for the synthesis of L-pipecolic acid from L-lysine by commercial L-lysine α-oxidase from Trichoderma viride and an extract of recombinant Escherichia coli cells coexpressing Δ1-piperideine-2- carboxylate reductase from Pseudomonas putida and glucose dehydrogenase from Bacillus subtilis is described. A laboratory-scale process provided 27 g/l of L-pipecolic acid in 99.7% e.e.
Preparation method of caine drug intermediate (S)-2-piperidinecarboxylic acid
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, (2021/06/22)
The invention discloses a preparation method of a caine drug intermediate (S)-2-piperidinecarboxylic acid. The preparation method specifically comprises the following steps of a) carrying out a one-pot reaction on 5-chlorovaleraldehyde, L-phenylglycinol and trimethylsilyl cyanide under the action of a catalyst A to obtain a compound as shown in a formula (I), wherein the catalyst A is magnesium diiodide, magnesium dibromide and magnesium perchlorate, (b) carrying out catalytic hydrogenation reaction on the compound as shown in the formula (I) to obtain (S)-2-cyano piperidine as shown in a formula (II), and (c) hydrolyzing the compound as shown in the formula (II) to obtain (S)-2-piperidinecarboxylic acid as shown in a formula (III). The preparation method utilizes cheap and easily available organic raw materials, and has the advantages of simple operation, mild reaction conditions, good stereoselectivity, high yield and the like.
A convenient and highly enantioselective synthesis of (S)-2-pipecolic acid: an efficient access to caine anesthetics
Yang, Yuyan,Li, Hua,You, Zhonglin,Zhang, Xingxian
, p. 3084 - 3089 (2021/08/12)
A novel and enantioselective synthesis of (S)-2-pipecolic acid (5) has been achieved from Oppolzer’s sultam (1) and ethyl N-(diphenylmethylene)glycinate (2) as readily available starting materials. The highly stereoselective alkylation of chiral glycine intermediate (3) with 1,4-dibromobutane afforded the key backbone of (S)-2-pipecolic acid (5) in one-step that was utilized into the preparation of the local anesthetics mepivacaine, ropivacaine and bupivacaine.
Cell-free biocatalytic syntheses of l-pipecolic acid: A dual strategy approach and process intensification in flow
Benítez-Mateos, Ana I.,Calvey, Liam,Paradisi, Francesca,Roura Padrosa, David
, p. 5310 - 5316 (2020/09/17)
As an alternative to the traditional chemical synthesis or in vivo production of l-pipecolic acid, we have developed two ex vivo strategies using purified and immobilised enzymes for the production of this key building block. Firstly, a transaminase capable of lysine ?-deamination was coupled with a novel pyrroline-5-carboxylate reductase, yielding 60% conversion at the 50 mM scale with free enzymes and in situ recycling of the cofactor. A second, simpler, redox neutral system was then constructed by combining the pyrroline-5-carboxylate reductase with a lysine-6-dehydrogenase. This bienzymatic system, with catalytic amount of free cofactor yielded >99% of pipecolic acid in batch and, following co-immobilisation of both enzymes, it was applied as a packed-bed reactor in continuous flow achieving again a molar conversion of >99% with 30 min residence time, and a space-time yield up to 2.5 g L-1 h-1. The sustainability of the system was further improved by a catch-and-release strategy to purify the product, and recovery and recycling of the cofactor.