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Journal articles on the topic 'Hydroxypipecolic acids'

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Author: Grafiati
Published: 10 March 2023

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1

Cochi, Anne, Domingo Gomez Pardo, and Janine Cossy. "Synthesis of 3-Hydroxypipecolic Acids." European Journal of Organic Chemistry 2013, no. 5 (January 14, 2013): 809–29. http://dx.doi.org/10.1002/ejoc.201201415.

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2

Krishnamurthy, Suvratha, Jalli Venkataprasad, Tarun Chand Vagvala, Tetsuji Moriguchi, and Akihiko Tsuge. "α-Chymotrypsin andl-acylase aided synthesis of 5-hydroxypipecolic acid via Jacobsen's hydrolytic kinetic resolution of epoxy amino acids." RSC Advances 5, no. 64 (2015): 52154–60. http://dx.doi.org/10.1039/c5ra09207h.

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5-hydroxypipecolic acid synthesis from intramolecular reaction of epoxy amino acids; enantiomers separated by hydrolase and diastereomeric epoxide separated by Jacobsen's hydrolytic kinetic resolution.
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3

Cochi, Anne, Domingo Gomez Pardo, and Janine Cossy. "ChemInform Abstract: Synthesis of 3-Hydroxypipecolic Acids." ChemInform 44, no. 28 (June 21, 2013): no. http://dx.doi.org/10.1002/chin.201328209.

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4

Alegret, Carlos, Xavier Ginesta, and Antoni Riera. "Asymmetric Synthesis ofcis-4- andtrans-3-Hydroxypipecolic Acids." European Journal of Organic Chemistry 2008, no. 10 (April 2008): 1789–96. http://dx.doi.org/10.1002/ejoc.200701103.

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5

Kite, Geoffrey C., and Michael J. Hughes. "Analysis of hydroxypipecolic acids by gas chromatography-mass spectrometry." Phytochemical Analysis 8, no. 6 (November 1997): 294–301. http://dx.doi.org/10.1002/(sici)1099-1565(199711/12)8:6<294::aid-pca372>3.0.co;2-r.

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6

Chiou, Wen-Hua, Gau-Hong Lin, and Chih-Wei Liang. "Facile Syntheses of Enantiopure 3-Hydroxypiperidine Derivatives and 3-Hydroxypipecolic Acids." Journal of Organic Chemistry 75, no. 5 (March 5, 2010): 1748–51. http://dx.doi.org/10.1021/jo902324h.

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7

Cordero, Franca M., Simona Bonollo, Fabrizio Machetti, and Alberto Brandi. "The Synthesis of 4-Hydroxypipecolic Acids by Stereoselective Cycloaddition of Configurationally Stable Nitrones." European Journal of Organic Chemistry 2006, no. 14 (July 2006): 3235–41. http://dx.doi.org/10.1002/ejoc.200600104.

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8

FERREIRA, F., C. GRECK, and P. GENET. "ChemInform Abstract: Stereocontrolled Syntheses of trans-3-Hydroxypipecolic Acids and Application to (-)-Swainsonine." ChemInform 29, no. 6 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199806241.

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9

Guan, Jiaojiao, Yilei Lu, Zixuan Dai, Songyin Zhao, Yan Xu, and Yao Nie. "R97 at “Handlebar” Binding Mode in Active Pocket Plays an Important Role in Fe(II)/α-Ketoglutaric Acid-Dependent Dioxygenase cis-P3H-Mediated Selective Synthesis of (2S,3R)-3-Hydroxypipecolic Acid." Molecules 28, no. 4 (February 15, 2023): 1854. http://dx.doi.org/10.3390/molecules28041854.

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Pipecolic acid (Pip) and its derivative hydroxypipecolic acids, such as (2S,3R)-3-hydroxypipecolic acid (cis-3-L-HyPip), are components of many natural and synthetic bioactive molecules. Fe(II)/α-ketoglutaric acid (Fe(II)/2-OG)-dependent dioxygenases can catalyze the hydroxylation of pipecolic acid. However, the available enzymes with desired activity and selectivity are limited. Herein, we compare the possible candidates in the Fe(II)/2-OG-dependent dioxygenase family, and cis-P3H is selected for potentially catalyzing selective hydroxylation of L-Pip. cis-P3H was further engineered to increase its catalytic efficiency toward L-Pip. By analyzing the structural confirmation and residue composition in substrate-binding pocket, a “handlebar” mode of molecular interactions is proposed. Using molecular docking, virtual mutation analysis, and dynamic simulations, R97, E112, L57, and G282 were identified as the key residues for subsequent site-directed saturation mutagenesis of cis-P3H. Consequently, the variant R97M showed an increased catalytic efficiency toward L-Pip. In this study, the kcat/Km value of the positive mutant R97M was about 1.83-fold that of the wild type. The mutation R97M would break the salt bridge between R97 and L-Pip and weaken the positive-positive interaction between R97 and R95. Therefore, the force on the amino and carboxyl groups of L-Pip was lightly balanced, allowing the molecule to be stabilized in the active pocket. These results provide a potential way of improving cis-P3H catalytic activity through rational protein engineering.
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10

Wang, Bing, and Run-Hua Liu. "Stereospecific, Flexible and Redox-Economic Asymmetric Synthesis ofcis- andtrans-3-Hydroxypipecolic Acids and ­Analogs." European Journal of Organic Chemistry 2009, no. 17 (June 2009): 2845–51. http://dx.doi.org/10.1002/ejoc.200900231.

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11

Jourdant, Angélique, and Jieping Zhu. "An efficient stereoselective and stereodivergent synthesis of (2R,3R)- and (2R,3S)-3-hydroxypipecolic acids." Tetrahedron Letters 41, no. 36 (September 2000): 7033–36. http://dx.doi.org/10.1016/s0040-4039(00)01207-7.

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12

Prier, Christopher K., Michael M. ‐C Lo, Hongming Li, and Nobuyoshi Yasuda. "Stereodivergent Synthesis of 3‐Hydroxyprolines and 3‐Hydroxypipecolic Acids via Ketoreductase‐Catalyzed Dynamic Kinetic Reduction." Advanced Synthesis & Catalysis 361, no. 22 (October 9, 2019): 5140–43. http://dx.doi.org/10.1002/adsc.201900871.

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13

Herdeis, C., and W. Engel. "Synthesis of unnatural 2R,5S-5-hydroxypipecolic acid via homochiral acyliminium ion - pipecolic acids - part III." Tetrahedron: Asymmetry 2, no. 10 (January 1991): 945–48. http://dx.doi.org/10.1016/s0957-4166(00)86132-7.

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14

Kokatla, Hari Prasad, Rima Lahiri, Pavan K. Kancharla, Venkata Ramana Doddi, and Yashwant D. Vankar. "Synthesis of (−)-Deoxoprosophylline, (+)-2-epi-Deoxoprosopinine, and (2R,3R)- and (2R,3S)-3-Hydroxypipecolic Acids fromd-Glycals." Journal of Organic Chemistry 75, no. 13 (July 2, 2010): 4608–11. http://dx.doi.org/10.1021/jo100489k.

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15

Jourdant, Angelique, and Jieping Zhu. "ChemInform Abstract: An Efficient Stereoselective and Stereodivergent Synthesis of (2R,3R)- and (2R,3S)-3-Hydroxypipecolic Acids." ChemInform 31, no. 48 (November 28, 2000): no. http://dx.doi.org/10.1002/chin.200048160.

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16

HERDEIS, C., and W. ENGEL. "ChemInform Abstract: Pipecolic Acids. Part 3. Synthesis of Unnatural 2R,5S-5- Hydroxypipecolic Acid via Homochiral Acyliminium Ion." ChemInform 23, no. 5 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199205275.

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17

Yildiz, Ipek, Melissa Mantz, Michael Hartmann, Tatyana Zeier, Jana Kessel, Corinna Thurow, Christiane Gatz, Patrick Petzsch, Karl Köhrer, and Jürgen Zeier. "The mobile SAR signal N-hydroxypipecolic acid induces NPR1-dependent transcriptional reprogramming and immune priming." Plant Physiology 186, no. 3 (April 19, 2021): 1679–705. http://dx.doi.org/10.1093/plphys/kiab166.

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Abstract N-hydroxypipecolic acid (NHP) accumulates in the plant foliage in response to a localized microbial attack and induces systemic acquired resistance (SAR) in distant leaf tissue. Previous studies indicated that pathogen inoculation of Arabidopsis (Arabidopsis thaliana) systemically activates SAR-related transcriptional reprogramming and a primed immune status in strict dependence of FLAVIN-DEPENDENT MONOOXYGENASE 1 (FMO1), which mediates the endogenous biosynthesis of NHP. Here, we show that elevations of NHP by exogenous treatment are sufficient to induce a SAR-reminiscent transcriptional response that mobilizes key components of immune surveillance and signal transduction. Exogenous NHP primes Arabidopsis wild-type and NHP-deficient fmo1 plants for a boosted induction of pathogen-triggered defenses, such as the biosynthesis of the stress hormone salicylic acid (SA), accumulation of the phytoalexin camalexin and branched-chain amino acids, as well as expression of defense-related genes. NHP also sensitizes the foliage systemically for enhanced SA-inducible gene expression. NHP-triggered SAR, transcriptional reprogramming, and defense priming are fortified by SA accumulation, and require the function of the transcriptional coregulator NON-EXPRESSOR OF PR GENES1 (NPR1). Our results suggest that NPR1 transduces NHP-activated immune signaling modes with predominantly SA-dependent and minor SA-independent features. They further support the notion that NHP functions as a mobile immune regulator capable of moving independently of active SA signaling between leaves to systemically activate immune responses.
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18

Jung, Jae-Chul, and Mitchell A. Avery. "Diastereoselective synthesis of (2S,5S)- and (2S,5R)-N-benzyloxycarbonyl-5-hydroxypipecolic acids from trans-4-hydroxy-l-proline." Tetrahedron: Asymmetry 17, no. 17 (October 2006): 2479–86. http://dx.doi.org/10.1016/j.tetasy.2006.07.035.

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19

Gomez Pardo, Domingo, Janine Cossy, Anne Cochi, Benjamin Burger, Cristina Navarro, Yang Zhao, and Theodore Cohen. "Enantioselective Ring Expansion of Prolinols: An Efficient and Short Synthesis of 2-Phenylpiperidin-3-ol Derivatives and 3-Hydroxypipecolic Acids." Synlett 2009, no. 13 (July 16, 2009): 2157–61. http://dx.doi.org/10.1055/s-0029-1217568.

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20

Kite, Geoffrey C., and Jan J. Wieringa. "Hydroxypipecolic acids and hydroxyprolines as chemical characters in Aphanocalyx, Bikinia and Tetraberlinia (Leguminosae: Caesalpinioideae): support for the segregation of Monopetalanthus." Biochemical Systematics and Ecology 31, no. 3 (March 2003): 279–92. http://dx.doi.org/10.1016/s0305-1978(02)00152-7.

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21

Yoshimura, Yuichi, Chiaki Ohara, Tatsushi Imahori, Yukako Saito, Atsushi Kato, Saori Miyauchi, Isao Adachi, and Hiroki Takahata. "Synthesis of both enantiomers of hydroxypipecolic acid derivatives equivalent to 5-azapyranuronic acids and evaluation of their inhibitory activities against glycosidases." Bioorganic & Medicinal Chemistry 16, no. 17 (September 2008): 8273–86. http://dx.doi.org/10.1016/j.bmc.2008.06.016.

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22

Mallick, Asadulla, Nitee Kumari, Rashmi Roy, Ashokkumar Palanivel, and Yashwant D. Vankar. "A Concise Synthesis of (2R,3R)- and (2R,3S)-3-Hydroxypipecolic Acids, and Total Synthesis of (-)-Deoxoprosopinine and (+)-2-epi-Deoxoprosopinine fromD-Glycals." European Journal of Organic Chemistry 2014, no. 25 (July 22, 2014): 5557–63. http://dx.doi.org/10.1002/ejoc.201402603.

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23

Mallick, Asadulla, Nitee Kumari, Rashmi Roy, Ashokkumar Palanivel, and Yashwant D. Vankar. "ChemInform Abstract: A Concise Synthesis of (2R,3R)- (Ia) and (2R,3S)-3-Hydroxypipecolic Acids (Ib), and Total Synthesis of (-)-Deoxoprosopinine (II) and (+)-2-epi-Deoxoprosopinine (III) from D-Glycals." ChemInform 46, no. 10 (February 19, 2015): no. http://dx.doi.org/10.1002/chin.201510271.

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24

"Stereoselective Synthesis of Hydroxypipecolic Acids." Synfacts 2008, no. 06 (May 21, 2008): 0567. http://dx.doi.org/10.1055/s-2008-1067070.

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