Category: 59234-40-1

《Enzyme-catalyzed hydrolysis of N-benzyloxycarbonyl-cis-2,6-(acetoxymethyl)piperidine. A facile route to optically active piperidines》 was written by Chenevert, Robert; Dickman, Michael. SDS of cas: 59234-40-1 And the article was included in Tetrahedron: Asymmetry on August 31 ,1992. The article conveys some information:

The first enzymic asymmetrization of a piperidine system is reported. Hydrolysis of N-benzyloxycarbonyl-cis-2,6-(acetoxymethyl)piperidine in the presence of Aspergillus niger lipase gave the corresponding 2R,6S monoacetate in good chem. yield and very high optical purity (ee ≥ 98%). In the experiment, the researchers used many compounds, for example, Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1SDS of cas: 59234-40-1)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine is ubiquitous structural motif widely occurred in diverse synthetically and naturally occurring bioactive molecules. Piperidines are an immensely important class of compounds medicinally: the piperidine ring is the most common heterocyclic subunit among FDA approved drugs.SDS of cas: 59234-40-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Quality Control of Cis-piperidine-2,6-dicarboxylic acidOn November 30, 1985 ,《The characterization of the specific binding of [3H]-N-acetylaspartylglutamate to rat brain membranes》 appeared in Journal of Neuroscience. The author of the article were Koller, Kerry J.; Coyle, Joseph T.. The article conveys some information:

3H-labeled N-acetylaspartylglutamate (NAAG) [3106-85-2] bound saturably and reversibly to rat brain crude synaptosomal membranes. Optimal binding occurred in Tris-HCl buffer, pH 7.2, at 37°, using previously frozen, preincubated membranes. Saturation experiments revealed an apparent dissociation constant of 383 nm and a Bmax of 31 pmol/mg protein. [3H]NAAG specific binding was displaceable by serine-O-sulfate  [626-69-7], quisqualate  [52809-07-1], ibotenate  [2552-55-8], and glutamate  [56-86-0], with Ki values in the nanomolar range, whereas the amino-phosphono analogs displaced [3H]NAAG in the micromolar range. No specific binding was found in peripheral tissues. Within the central nervous system, the thalamus exhibited the greatest amount of binding, whereas binding was lowest in cortex. Ca2+ enhanced the specific binding, whereas Na+ caused a concentration-dependent inhibition. It appears that [3H]NAAG labels an acidic amino acid receptor site designated A-4, which recognizes the antagonist, 2-amino-4-phosphonobutyric acid, and this receptor may mediate the neurophysiol. effects of endogenous NAAG. After reading the article, we found that the author used Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1Quality Control of Cis-piperidine-2,6-dicarboxylic acid)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.Quality Control of Cis-piperidine-2,6-dicarboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

《A stochastic model for the synthesis and degradation of natural organic matter. Part III: Modeling Cu(II) complexation》 was written by Cabaniss, Stephen E.; Maurice, Patricia A.; Madey, Greg. Quality Control of Cis-piperidine-2,6-dicarboxylic acid And the article was included in Applied Geochemistry on August 31 ,2007. The article conveys some information:

An agent-based biogeochem. model has been developed which begins with biochem. precursor mols. and simulates the transformation and degradation of natural organic matter (NOM). This paper presents an empirical quant. structure activity relationship (QSAR) which uses the numbers of ligand groups, charge d. and heteroatom d. of a mol. to estimate Cu-binding affinity (K’Cu) at pH 7.0 and ionic strength 0.10 for the mols. in this model. Calibration of this QSAR on a set of 41 model compounds gives a root mean square error of 0.88 log units and r2 =0.93. Two simulated NOM assemblages, one beginning with small mols. (tannins, terpenoids, flavonoids) and one with biopolymers (protein, lignin), give markedly different distributions of log K’Cu. However, calculations based on these log K’Cu distributions agree qual. with published exptl. Cu(II) titration data from river and lake NOM samples. In the part of experimental materials, we found many familiar compounds, such as Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1Quality Control of Cis-piperidine-2,6-dicarboxylic acid)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine is ubiquitous structural motif widely occurred in diverse synthetically and naturally occurring bioactive molecules. Piperidines are an immensely important class of compounds medicinally: the piperidine ring is the most common heterocyclic subunit among FDA approved drugs.Quality Control of Cis-piperidine-2,6-dicarboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Product Details of 59234-40-1On September 30, 1982 ,《The effects of cyclic dicarboxylic acids on spontaneous and amino acid-evoked activity of rat cortical neurons》 was published in British Journal of Pharmacology. The article was written by Birley, S.; Collins, J. F.; Perkins, M. N.; Stone, T. W.. The article contains the following contents:

At relatively low ejecting currents (10-25 nA), cis-2,3-piperidinedicarboxylic acid (I) [46026-75-9] had no effect on spontaneous firing in neurons of rat cerebral cortex, but selectively antagonized the excitation evoked by N-methyl-D-aspartate (II) without affecting responses to quisqualate or kainate. At higher ejecting currents (60-100 nA), responses to all 3 agonists were reduced. Other cis-piperidinedicarboxylic acids and piperazine-2,3-dicarboxylic acid  [84619-47-6] had only weak and variable effects on cell firing and responses to II, quisqualate, kainate, glutamate, and aspartate. Excitation was produced by 2,3-pyridinedicarboxylic acid (quinolinic acid) [89-00-9] in all cortical neurons tested. Thus, quinolinic acid may be of physiol. interest as a potential endogenous excitant in the nervous system and I and its N-Me derivative may be of use in studies of receptor pharmacol. and the identification of synaptic transmitters. In the experiment, the researchers used many compounds, for example, Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1Product Details of 59234-40-1)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.Product Details of 59234-40-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Madsen, Ulf; Brehm, Lotte; Schaumburg, Kjeld; Joergensen, Flemming S.; Krogsgaard-Larsen, Povl published an article on January 31 ,1990. The article was titled 《Relationship between structure, conformational flexibility, and biological activity of agonists and antagonists at the N-methyl-D-aspartic acid subtype of excitatory amino acid receptors》, and you may find the article in Journal of Medicinal Chemistry.Application In Synthesis of Cis-piperidine-2,6-dicarboxylic acid The information in the text is summarized as follows:

The relationship between conformational flexibility and agonist or antagonist actions at the N-methyl-D-aspartic acid (NMDA) subtype of central L-glutamic acid (GLU) receptors of a series of racemic piperidinedicarboxylic acids (PDAs) was studied. The conformational analyses were based on 1H NMR spectroscopy and supported by computer simulations and mol. mechanics calculations While the trans-forms of 2,3-PDA and 2,4-PDA and cis-2,5-PDA show NMDA receptor agonist activities, cis-2,3-PDA and cis-2,4-PDA are NMDA antagonists. The compounds trans-2,5-PDA and cis-2,6-PDA did not interact with NMDA receptors. Each of the 3 cyclic acidic amino acids showing NMDA agonist activities existed as an equilibrium mixture of 2 conformers in aqueous solution In contrast, the NMDA antagonists cis-2,3-PDA and cis-2,4-PDA as well as the inactive compounds trans-2,5-PDA and cis-2,6-PDA exist predominantly in a single conformation. These results seem to indicate that a certain degree of conformational flexibility of analogs of GLU is prerequisite for activation of, but not for binding to, the NMDA receptor. The results came from multiple reactions, including the reaction of Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1Application In Synthesis of Cis-piperidine-2,6-dicarboxylic acid)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.Application In Synthesis of Cis-piperidine-2,6-dicarboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthetic Route of C7H11NO4On March 15, 2005, Turner, Jennifer J.; Gerrard, Juliet A.; Hutton, Craig A. published an article in Bioorganic & Medicinal Chemistry. The article was 《Heterocyclic inhibitors of dihydrodipicolinate synthase are not competitive》. The article mentions the following:

A series of piperidine- and pyridine-2,6-dicarboxylate derivatives has been evaluated as potential inhibitors of dihydrodipicolinate synthase (DHDPS). The compounds were designed with oxygen functionality at the C-4 position in order to mimic the putative enzyme product HTHDP. Most compounds displayed weak-moderate inhibition of DHDPS. Addnl., the most potent inhibitors were shown not to be competitive, indicating they do not bind at the active site. Discrepancies between the two common assay systems-the imidazole assay and the coupled assay-were observed which are attributed to inherent problems in the imidazole assay, leading to artifactually low Ki measurements. In the experiment, the researchers used Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1Synthetic Route of C7H11NO4)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine is ubiquitous structural motif widely occurred in diverse synthetically and naturally occurring bioactive molecules. Piperidines are an immensely important class of compounds medicinally: the piperidine ring is the most common heterocyclic subunit among FDA approved drugs.Synthetic Route of C7H11NO4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

SDS of cas: 59234-40-1On September 30, 2017 ,《Stereo-selective preparation of teneraic acid, trans-(2S,6S)-piperidine-2,6-dicarboxylic acid, via anodic oxidation and cobalt-catalyzed carbonylation》 was published in Chemical & Pharmaceutical Bulletin. The article was written by Amino, Yusuke; Nishi, Seiichi; Izawa, Kunisuke. The article contains the following contents:

Teneraic acid (piperidine-2,6-dicarboxylic acid) is a naturally occurring imino acid that comprises of three stereoisomers due to its two asym. centers at C2 and C6. The configuration of natural teneraic acid is reported to correspond to trans-(2S,6S). However, a few studies are focused on the stereospecific synthesis of trans-(2S,6S)-teneraic acid. The present study investigates a convenient synthetic method that includes regiospecific anodic oxidation and stereospecific cobalt-catalyzed carbonylation to obtain trans-(2S,6S)-teneraic acid. Me (S)-N-benzoyl-α-methoxypipecolate, the key intermediate that displays a structure that corresponds to an intermediate (N-α-hydroxyalkyl amide) of intramol. amidocarbonylation, was obtained via an anodic oxidation of Me (S)-N-benzoylpipecolate. Subsequently, cobalt-catalyzed carbonylation converted the Me (S)-N-benzoyl-α-methoxypipecolate to trans-(2S,6S)-N-benzoyl-teneraic acid di-Me ester in good optical purity (>95% enantiomeric excess (ee)) and modest yield (63%). Finally, de-protection occurred via acidic hydrolysis to obtain trans-(2S,6S)-teneraic acid. The stereochem. of synthesized teneraic acid was confirmed as corresponding to trans-(2S,6S) by comparing its phys. properties with those of a cis-meso-isomer and those of a trans-(2S,6S)-isomer that were reported in previous studies. In the experiment, the researchers used Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1SDS of cas: 59234-40-1)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine-containing compounds are also frequently employed in synthesis as ligands or auxiliaries. Accordingly, many efforts have been devoted to the development of novel methods for the synthesis of these compounds over the years.SDS of cas: 59234-40-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Quality Control of Cis-piperidine-2,6-dicarboxylic acidOn May 15, 1986 ,《Studies on the active site of succinyl-CoA:tetrahydrodipicolinate N-succinyltransferase. Characterization using analogs of tetrahydrodipicolinate》 appeared in Journal of Biological Chemistry. The author of the article were Berges, David A.; DeWolf, Walter E. Jr.; Dunn, George L.; Newman, David J.; Schmidt, Stanley J.; Taggart, John J.; Gilvarg, Charles. The article conveys some information:

Cyclic and acyclic analogs of tetrahydrodipicolinate (THDPA) were evaluated in a study of the active site of THDPA N-succinyltransferase (I). In addition to the natural substrate, THDPA, 1 cyclic and several acyclic compounds were also succinylated. 2-Hydroxytetrahydropyran-2,6-dicarboxylic acid was a potent competitive inhibitor with a Ki of 58 nM. Based on the results of this study, a stereochem. model for the succinylation of THDPA is proposed. The major features of this model are as follows. (1) I binds THDPA (L-configuration). (2) Hydration of the imine group follows to give 2-hydroxypiperidine-2,6-dicarboxylic acid in which the 2 carboxyl groups are trans. (3) Succinylation then occurs and the ring opens to give the acyclic product. Apparently, 2-hydroxytetrahydropyran-2,6-dicarboxylic acid is a transition state analog by virtue of the fact that it structurally resembles the hydrated intermediate. The experimental process involved the reaction of Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1Quality Control of Cis-piperidine-2,6-dicarboxylic acid)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine is a key saturated heterocyclic scaffold found in several of the top-selling small molecule pharmaceuticals and natural alkaloids, with a diverse range of biological activities. Hence, continuous efforts have been made to develop convenient methods to prepare piperidine derivatives.Quality Control of Cis-piperidine-2,6-dicarboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthetic Route of C7H11NO4On March 15, 2005, Turner, Jennifer J.; Gerrard, Juliet A.; Hutton, Craig A. published an article in Bioorganic & Medicinal Chemistry. The article was 《Heterocyclic inhibitors of dihydrodipicolinate synthase are not competitive》. The article mentions the following:

A series of piperidine- and pyridine-2,6-dicarboxylate derivatives has been evaluated as potential inhibitors of dihydrodipicolinate synthase (DHDPS). The compounds were designed with oxygen functionality at the C-4 position in order to mimic the putative enzyme product HTHDP. Most compounds displayed weak-moderate inhibition of DHDPS. Addnl., the most potent inhibitors were shown not to be competitive, indicating they do not bind at the active site. Discrepancies between the two common assay systems-the imidazole assay and the coupled assay-were observed which are attributed to inherent problems in the imidazole assay, leading to artifactually low Ki measurements. In the experiment, the researchers used Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1Synthetic Route of C7H11NO4)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine is ubiquitous structural motif widely occurred in diverse synthetically and naturally occurring bioactive molecules. Piperidines are an immensely important class of compounds medicinally: the piperidine ring is the most common heterocyclic subunit among FDA approved drugs.Synthetic Route of C7H11NO4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthetic Route of C7H11NO4On March 15, 2005, Turner, Jennifer J.; Gerrard, Juliet A.; Hutton, Craig A. published an article in Bioorganic & Medicinal Chemistry. The article was 《Heterocyclic inhibitors of dihydrodipicolinate synthase are not competitive》. The article mentions the following:

A series of piperidine- and pyridine-2,6-dicarboxylate derivatives has been evaluated as potential inhibitors of dihydrodipicolinate synthase (DHDPS). The compounds were designed with oxygen functionality at the C-4 position in order to mimic the putative enzyme product HTHDP. Most compounds displayed weak-moderate inhibition of DHDPS. Addnl., the most potent inhibitors were shown not to be competitive, indicating they do not bind at the active site. Discrepancies between the two common assay systems-the imidazole assay and the coupled assay-were observed which are attributed to inherent problems in the imidazole assay, leading to artifactually low Ki measurements. In the experiment, the researchers used Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1Synthetic Route of C7H11NO4)

Cis-piperidine-2,6-dicarboxylic acid(cas: 59234-40-1) is a member of piperidine. Piperidine is ubiquitous structural motif widely occurred in diverse synthetically and naturally occurring bioactive molecules. Piperidines are an immensely important class of compounds medicinally: the piperidine ring is the most common heterocyclic subunit among FDA approved drugs.Synthetic Route of C7H11NO4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem