Category: 86069-86-5

Synthesis and structural and biological studies of efrapeptin C analogues was written by Jost, Micha;Weigelt, Sven;Huber, Thomas;Majer, Zsuzsanna;Greie, Joerg-Christian;Altendorf, Karlheinz;Sewald, Norbert. And the article was included in Chemistry & Biodiversity in 2007.Recommanded Product: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:

A series of analogs of efrapeptin C, with variations in the central tripeptide epitope Leu-β-Ala-Gly (positions 6-8), were prepared by a combination of solid- and solution-phase peptide syntheses. The conformations of the modified compounds (Xaa⁶-Xaa⁷-Xaa⁸ = Leu-Gly-βAla, β-Ala-Leu-Gly, β³HLeu-Gly-Gly, Leu-β³-HPhe-Gly, Leu-Aib-Gly) were investigated by circular-dichroism (CD) spectroscopy to differentiate between 3₁₀– and α-helical secondary structures. The inhibitory activities of the new compounds towards F₁-ATPase from E. coli were determined Threee modified congeners were less active by one order of magnitude compared to efrapeptin C (K_i 10 μM), and one was completely inactive. Our experiments demonstrate that the flexible, central tripeptide epitope, comprising positions 6-8 in efrapeptin C, is crucial for mol. recognition, even slight sequence modifications being hardly tolerated. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Recommanded Product: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an axial position, and the other in an equatorial position.Recommanded Product: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis and structural and biological studies of efrapeptin C analogues was written by Jost, Micha;Weigelt, Sven;Huber, Thomas;Majer, Zsuzsanna;Greie, Joerg-Christian;Altendorf, Karlheinz;Sewald, Norbert. And the article was included in Chemistry & Biodiversity in 2007.Recommanded Product: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:

A series of analogs of efrapeptin C, with variations in the central tripeptide epitope Leu-β-Ala-Gly (positions 6-8), were prepared by a combination of solid- and solution-phase peptide syntheses. The conformations of the modified compounds (Xaa⁶-Xaa⁷-Xaa⁸ = Leu-Gly-βAla, β-Ala-Leu-Gly, β³HLeu-Gly-Gly, Leu-β³-HPhe-Gly, Leu-Aib-Gly) were investigated by circular-dichroism (CD) spectroscopy to differentiate between 3₁₀– and α-helical secondary structures. The inhibitory activities of the new compounds towards F₁-ATPase from E. coli were determined Threee modified congeners were less active by one order of magnitude compared to efrapeptin C (K_i 10 μM), and one was completely inactive. Our experiments demonstrate that the flexible, central tripeptide epitope, comprising positions 6-8 in efrapeptin C, is crucial for mol. recognition, even slight sequence modifications being hardly tolerated. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Recommanded Product: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.Recommanded Product: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Construction of peptide macrocycles via radical-mediated intramolecular C-H alkylations was written by Hu, Xiafei;Chen, Xiangxiang;Li, Bo;He, Gang;Chen, Gong. And the article was included in Organic Letters in 2021.Quality Control of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:

Enzyme-catalyzed radical-mediated C-H functionalization reactions allow nature to create natural products of unusual three-dimensional structures from simple linear peptide precursors. In comparison, chemist’s ability to harness radical C-H functionalization reactions for synthesis of complex peptides remains limited. In this work, new methods have been developed to construct peptide macrocycles via radical-mediated intramol. C-H alkylation reactions under photoredox catalysis. Linear peptide precursors equipped with a C-terminal N-(acyloxy)phthalimide ester can cyclize with the α C-H bond of N-terminal glycine or aryl C-H bond of N-heteroarene capping units in high yield and selectivity under mild conditions. The strategy uses the C-H cyclization step to incorporate lysine, homolysine, and various heteroarene-derived amino acid linchpins into peptide macrocycles, enabling convergent and flexible synthesis of complex peptide macrocycles from simple building blocks. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Quality Control of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.Quality Control of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Construction of peptide macrocycles via radical-mediated intramolecular C-H alkylations was written by Hu, Xiafei;Chen, Xiangxiang;Li, Bo;He, Gang;Chen, Gong. And the article was included in Organic Letters in 2021.Application In Synthesis of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:

Enzyme-catalyzed radical-mediated C-H functionalization reactions allow nature to create natural products of unusual three-dimensional structures from simple linear peptide precursors. In comparison, chemist’s ability to harness radical C-H functionalization reactions for synthesis of complex peptides remains limited. In this work, new methods have been developed to construct peptide macrocycles via radical-mediated intramol. C-H alkylation reactions under photoredox catalysis. Linear peptide precursors equipped with a C-terminal N-(acyloxy)phthalimide ester can cyclize with the α C-H bond of N-terminal glycine or aryl C-H bond of N-heteroarene capping units in high yield and selectivity under mild conditions. The strategy uses the C-H cyclization step to incorporate lysine, homolysine, and various heteroarene-derived amino acid linchpins into peptide macrocycles, enabling convergent and flexible synthesis of complex peptide macrocycles from simple building blocks. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Application In Synthesis of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. Piperidine derivatives are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents.Application In Synthesis of (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Macrocyclic Peptides as a Novel Class of NNMT Inhibitors: A SAR Study Aimed at Inhibitory Activity in the Cell was written by Hayashi, Kyohei;Uehara, Shota;Yamamoto, Shiho;Cary, Douglas R.;Nishikawa, Junichi;Ueda, Taichi;Ozasa, Hiroki;Mihara, Kousuke;Yoshimura, Norito;Kawai, Taeko;Ono, Takashi;Yamamoto, Saki;Fumoto, Masataka;Mikamiyama, Hidenori. And the article was included in ACS Medicinal Chemistry Letters in 2021.Recommanded Product: 86069-86-5 The following contents are mentioned in the article:

Nicotinamide N-methyltransferase (NNMT), which catalyzes the methylation of nicotinamide, is a cytosolic enzyme that has attracted much attention as a therapeutic target for a variety of diseases. However, despite the considerable interest in this target, reports of NNMT inhibitors have still been limited to date. In this work, utilizing in vitro translated macrocyclic peptide libraries, we identified peptide 1 as a novel class of NNMT inhibitors. Further exploration based on the X-ray cocrystal structures of the peptides with NNMT provided a dramatic improvement in inhibitory activity (peptide 23: IC₅₀ = 0.15 nM). Furthermore, by balance of the peptides’ lipophilicity and biol. activity, inhibitory activity against NNMT in cell-based assay was successfully achieved (peptide 26: cell-based IC₅₀ = 770 nM). These findings illuminate the potential of cyclic peptides as a relatively new drug discovery modality even for intracellular targets. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Recommanded Product: 86069-86-5).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives.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. Piperidine derivatives are being utilized in different ways as anticancer, antiviral, antimalarial, antimicrobial, antifungal, antihypertension, analgesic, anti-inflammatory, anti-Alzheimer, antipsychotic and/or anticoagulant agents.Recommanded Product: 86069-86-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Macrocyclic Peptides as a Novel Class of NNMT Inhibitors: A SAR Study Aimed at Inhibitory Activity in the Cell was written by Hayashi, Kyohei;Uehara, Shota;Yamamoto, Shiho;Cary, Douglas R.;Nishikawa, Junichi;Ueda, Taichi;Ozasa, Hiroki;Mihara, Kousuke;Yoshimura, Norito;Kawai, Taeko;Ono, Takashi;Yamamoto, Saki;Fumoto, Masataka;Mikamiyama, Hidenori. And the article was included in ACS Medicinal Chemistry Letters in 2021.Formula: C21H21NO4 The following contents are mentioned in the article:

Nicotinamide N-methyltransferase (NNMT), which catalyzes the methylation of nicotinamide, is a cytosolic enzyme that has attracted much attention as a therapeutic target for a variety of diseases. However, despite the considerable interest in this target, reports of NNMT inhibitors have still been limited to date. In this work, utilizing in vitro translated macrocyclic peptide libraries, we identified peptide 1 as a novel class of NNMT inhibitors. Further exploration based on the X-ray cocrystal structures of the peptides with NNMT provided a dramatic improvement in inhibitory activity (peptide 23: IC₅₀ = 0.15 nM). Furthermore, by balance of the peptides’ lipophilicity and biol. activity, inhibitory activity against NNMT in cell-based assay was successfully achieved (peptide 26: cell-based IC₅₀ = 770 nM). These findings illuminate the potential of cyclic peptides as a relatively new drug discovery modality even for intracellular targets. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Formula: C21H21NO4).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an axial position, and the other in an equatorial position.Formula: C21H21NO4

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Analogues of AVP modified in the N-terminal part of the molecule with Pip isomers: TFA-catalyzed peptide bond hydrolysis was written by Sobolewski, Dariusz;Prahl, Adam;Kwiatkowska, Anna;Slaninova, Jirina;Lammek, Bernard. And the article was included in Journal of Peptide Science in 2009.Recommanded Product: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid The following contents are mentioned in the article:

Using SPPS techniques, six new analogs of AVP (arginine vasopressin) and some of its agonists were synthesized. The peptides were designed by substitution of Phe at position 3 of AVP, [Mpa¹] AVP (dAVP) and [Mpa¹,Val⁴,D-Arg⁸]VP (dVDAVP) with L– or D-Pip (Mpa = 3-mercaptopropionic acid; Pip = pipecolic acid, a non-coded α-imino acid, also known as homoproline). Surprisingly enough, both the analogs of AVP and [Mpa¹]AVP with identical substituents at position 2 turned out to be highly sensitive to TFA used for the deprotection and resin cleavage step, and it was the reason why the authors were not able to obtain these four peptides. The mechanisms of their fragmentation were proposed in this study. Unfortunately, all the new analogs were inactive in bioassays for the pressor, antidiuretic and uterotonic in vitro activities in the rat. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Recommanded Product: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Fluorinated piperidines are also the subject of continued interest in medicinal chemistry, for example in the synthesis of selective dipeptidyl peptidase II (DPP II) inhibitors. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions.Recommanded Product: (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Analogues of AVP modified in the N-terminal part of the molecule with Pip isomers: TFA-catalyzed peptide bond hydrolysis was written by Sobolewski, Dariusz;Prahl, Adam;Kwiatkowska, Anna;Slaninova, Jirina;Lammek, Bernard. And the article was included in Journal of Peptide Science in 2009.Category: piperidines The following contents are mentioned in the article:

Using SPPS techniques, six new analogs of AVP (arginine vasopressin) and some of its agonists were synthesized. The peptides were designed by substitution of Phe at position 3 of AVP, [Mpa¹] AVP (dAVP) and [Mpa¹,Val⁴,D-Arg⁸]VP (dVDAVP) with L– or D-Pip (Mpa = 3-mercaptopropionic acid; Pip = pipecolic acid, a non-coded α-imino acid, also known as homoproline). Surprisingly enough, both the analogs of AVP and [Mpa¹]AVP with identical substituents at position 2 turned out to be highly sensitive to TFA used for the deprotection and resin cleavage step, and it was the reason why the authors were not able to obtain these four peptides. The mechanisms of their fragmentation were proposed in this study. Unfortunately, all the new analogs were inactive in bioassays for the pressor, antidiuretic and uterotonic in vitro activities in the rat. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Category: piperidines).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Category: piperidines

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Introduction of Pro and its analogues in the conserved P₁‘ position of trypsin inhibitor SFTI-1 retains its inhibitory activity was written by Legowska, Anna;Debowski, Dawid;Lukajtis, Rafal;Sztabkowska, Emilia;Mizeria, Aneta;Brzozowski, Krzysztof;Wysocka, Magdalena;Lesner, Adam;Rolka, Krzysztof. And the article was included in Protein & Peptide Letters in 2011.SDS of cas: 86069-86-5 The following contents are mentioned in the article:

A number of monocyclic SFTI-1 analogs modified in the conserved inhibitor P₁‘ position by Pro, its L-hydroxyproline (Hyp) derivative as well as mimetics with different ring size were synthesized by the solid-phase method. Replacement of Ser6 by Pro, Hyp, and a four-member ring, L-azetidine-2-carboxylic acid (Aze), retained trypsin or chymotrypsin inhibitory activity. The determined association equilibrium constants of these analogs with a cognate enzyme were about two orders of magnitude lower than those obtained for ones with conserved Ser6. In all analogs, with the exception of one, [Phe⁵,Aze⁶]SFTI-1, the P₁-P₁‘ reactive site remained intact. The results provide first evidence that the conserved Ser in the P₁‘ position of Bowman-Birk inhibitors can be successfully replaced by an amino acid with a secondary amine group. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5SDS of cas: 86069-86-5).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Fluorinated piperidines are also the subject of continued interest in medicinal chemistry, for example in the synthesis of selective dipeptidyl peptidase II (DPP II) inhibitors. Piperidine derivatives are also used in solid-phase peptide synthesis (SPPS) and many degradation reactions.SDS of cas: 86069-86-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Introduction of Pro and its analogues in the conserved P₁‘ position of trypsin inhibitor SFTI-1 retains its inhibitory activity was written by Legowska, Anna;Debowski, Dawid;Lukajtis, Rafal;Sztabkowska, Emilia;Mizeria, Aneta;Brzozowski, Krzysztof;Wysocka, Magdalena;Lesner, Adam;Rolka, Krzysztof. And the article was included in Protein & Peptide Letters in 2011.Recommanded Product: 86069-86-5 The following contents are mentioned in the article:

A number of monocyclic SFTI-1 analogs modified in the conserved inhibitor P₁‘ position by Pro, its L-hydroxyproline (Hyp) derivative as well as mimetics with different ring size were synthesized by the solid-phase method. Replacement of Ser6 by Pro, Hyp, and a four-member ring, L-azetidine-2-carboxylic acid (Aze), retained trypsin or chymotrypsin inhibitory activity. The determined association equilibrium constants of these analogs with a cognate enzyme were about two orders of magnitude lower than those obtained for ones with conserved Ser6. In all analogs, with the exception of one, [Phe⁵,Aze⁶]SFTI-1, the P₁-P₁‘ reactive site remained intact. The results provide first evidence that the conserved Ser in the P₁‘ position of Bowman-Birk inhibitors can be successfully replaced by an amino acid with a secondary amine group. This study involved multiple reactions and reactants, such as (S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5Recommanded Product: 86069-86-5).

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (cas: 86069-86-5) belongs to piperidine derivatives. The piperidine ring can be found not only in more than half of the currently known structures of alkaloids, but also in many natural or synthetic compounds with interesting biological activities. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.Recommanded Product: 86069-86-5

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem