Dirigent isoflavene-forming PsPTS2: 3D structure, stereochemical, and kinetic characterization comparison with pterocarpan-forming PsPTS1 homolog in pea

Meng, Qingyan; Moinuddin, Syed G.A.; Celoy, Rhodesia M.; Smith, Clyde A.; Young, Robert P.; Costa, Michael A.; Freeman, Rachel A.; Fukaya, Masashi; Kim, Doo Nam; Cort, John R.; Hawes, Martha C.; van Etten, Hans D.; Pandey, Pankaj; Chittiboyina, Amar G.; Ferreira, Daneel; Davin, Laurence B.; Lewis, Norman G.

doi:10.1016/j.jbc.2024.105647

Title: Dirigent isoflavene-forming PsPTS2: 3D structure, stereochemical, and kinetic characterization comparison with pterocarpan-forming PsPTS1 homolog in pea

Journal Article · Sun Jan 14 00:00:00 EST 2024 · Journal of Biological Chemistry

DOI:https://doi.org/10.1016/j.jbc.2024.105647· OSTI ID:2335877

Meng, Qingyan ^[1]; Moinuddin, Syed G.A. ^[1]; Celoy, Rhodesia M. ^[2]; Smith, Clyde A. ^[3];

^[4]; Costa, Michael A. ^[1]; Freeman, Rachel A. ^[1]; Fukaya, Masashi ^[1];

^[4];

^[5]; Hawes, Martha C. ^[2]; van Etten, Hans D. ^[2];

^[6];

^[6]; Ferreira, Daneel ^[6];

^[1];

^[1]

Washington State University, Pullman, WA (United States)
University of Arizona, Tucson, AZ (United States)
SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States). Stanford Synchrotron Radiation Lightsource (SSRL)
Pacific Northwest National Laboratory (PNNL), Richland, WA (United States). Earth and Biological Sciences Directorate
Washington State University, Pullman, WA (United States); Pacific Northwest National Laboratory (PNNL), Richland, WA (United States). Earth and Biological Sciences Directorate
University of Missouri, University, MO (United States)

Pea (legume plant defense) phytoalexin pterocarpans (–)-maackiain and (+)-pisatin have opposite C6a and C11a configurations, but how this occurs biosynthetically is unknown. Herein, pea dirigent-protein (DP) PsPTS2, which generates 7,2'-dihydroxy-4',5'-methylenedioxyisoflav-3-ene (DMDIF), was investigated as regards stereoselectivity towards four possible 7,2'-dihydroxy-4',5'-methylenedioxyisoflavan-4-ol (DMDI) stereoisomers. Each DMDI stereoisomer configuration was determined using NMR spectroscopy, electronic circular dichroism, and molecular orbital analyses. PsPTS2 efficiently converted cis-(3R,4R)-DMDI into DMDIF, this being 20-fold faster than with the trans-(3R,4S)-isomer. The 4R-configured substrate’s near ß-axial OH orientation significantly enhanced its leaving group abilities in creating intermediate A-ring mono-quinone methide (QM), whereas the 4S-isomer’s 4-OH group α-equatorial orientation was a poorer leaving group. Substrate docking simulations also indicated that the 4R-configured ß-axial OH was closest to the Asp catalytic center, whereas the 4S-isomer’s α-equatorial OH was further away. Neither cis-(3S,4S)- nor trans-(3S, 4R)-DMDIs were substrates, even with the former having the same C3/C4 stereochemistry as (+)-pisatin. PsPTS2, assayed with cis-(3R,4R)-7,2'-dihydroxy-4'-methoxyisoflavan-4-ol [cis-(3R,4R)-DMI] and its C3/C4 stereoisomers, gave 2',7-dihydroxy-4'-methoxyisoflav-3-ene (DMIF), with the same substrate stereoselectivity. DP homologs may exist in licorice (Glycyrrhiza pallidiflora) and the tree legume Bolusanthus speciosus, as DMIF is found in both. PsPTS1 preferentially utilized cis-(3R,4R)-DMDI to give (–)-maackiain, this being 2200-fold more efficient than with cis-(3R,4R)-DMI. PsPTS1 also slowly converted trans-(3S,4R)-DMDI into (+)-maackiain, again reflecting the better 4R configured OH leaving group. Pea PsPTS2 and PsPTS1 provisionally provide a facile DP-engendered means to enable differing C6a and C11a configurations in (+)-pisatin and (–)-maackiain. Both DP transformations are considered to occur via DP-engendered generation of an identical mono-QM bound intermediate, which with PsPTS2 either re-aromatizes to give DMDIF or with PsPTS1 undergoes intramolecular cyclization to afford (–)-maackiain. Substrate docking simulations using PsPTS2 (2.5 Å resolution) and PsPTS1 (1.5 Å resolution) plausibly indicate that cis-(3R,4R)-DMDI binds in the anti-configuration in the PsPTS2 active site to afford DMDIF, and the syn-configuration in PsPTS1 to give maackiain.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States); SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Biological and Environmental Research (BER); National Institutes of Health (NIH)

Grant/Contract Number:: AC05-76RL01830; AC02-76SF00515; P41GM103393; MRI 1338056

OSTI ID:: 2335877

Report Number(s):: PNNL-SA-188847

Journal Information:: Journal of Biological Chemistry, Vol. 300, Issue 3; ISSN 0021-9258

Publisher:: American Society for Biochemistry and Molecular BiologyCopyright Statement

Country of Publication:: United States

Language:: English

References (77)

Absolute configuration determination of isoflavan-4-ol stereoisomers Kim, Mihyang; Won, Dongho; Han, Jaehong Bioorganic & Medicinal Chemistry Letters, Vol. 20, Issue 15 https://doi.org/10.1016/j.bmcl.2010.06.074	journal	August 2010
CHAINSAW : a program for mutating pdb files used as templates in molecular replacement Stein, Norman Journal of Applied Crystallography, Vol. 41, Issue 3 https://doi.org/10.1107/S0021889808006985	journal	April 2008
QTPIE: Charge transfer with polarization current equalization. A fluctuating charge model with correct asymptotics Chen, Jiahao; Martínez, Todd J. Chemical Physics Letters, Vol. 438, Issue 4-6 https://doi.org/10.1016/j.cplett.2007.02.065	journal	April 2007
Linking Crystallographic Model and Data Quality Karplus, P. A.; Diederichs, K. Science, Vol. 336, Issue 6084 https://doi.org/10.1126/science.1218231	journal	May 2012
Absolute configurations of isoflavan-4-ol stereoisomers Won, Dongho; Shin, Bok-Kyu; Kang, Suil Bioorganic & Medicinal Chemistry Letters, Vol. 18, Issue 6 https://doi.org/10.1016/j.bmcl.2008.01.116	journal	March 2008
Pterocarpan synthase (PTS) structures suggest a common quinone methide–stabilizing function in dirigent proteins and proteins with dirigent-like domains Meng, Qingyan; Moinuddin, Syed G. A.; Kim, Sung-Jin Journal of Biological Chemistry, Vol. 295, Issue 33 https://doi.org/10.1074/jbc.RA120.012444	journal	August 2020
Introduction to the BioChemical Library (BCL): An Application-Based Open-Source Toolkit for Integrated Cheminformatics and Machine Learning in Computer-Aided Drug Discovery Brown, Benjamin P.; Vu, Oanh; Geanes, Alexander R. Frontiers in Pharmacology, Vol. 13 https://doi.org/10.3389/fphar.2022.833099	journal	February 2022
Antimicrobial and antioxidant flavonoids from the root wood of Bolusanthus speciosus Erasto, Paul; Bojase-Moleta, Gomotsang; Majinda, Runner R. T. Phytochemistry, Vol. 65, Issue 7 https://doi.org/10.1016/j.phytochem.2004.02.011	journal	April 2004
Assignment of the absolute configuration of hepatoprotective highly oxygenated triterpenoids using X-ray, ECD, NMR J -based configurational analysis and HSQC overlay experiments Wang, Xiaojuan; Liu, Jiabao; Pandey, Pankaj Biochimica et Biophysica Acta (BBA) - General Subjects, Vol. 1861, Issue 12 https://doi.org/10.1016/j.bbagen.2017.09.001	journal	December 2017
Opposite Stereoselectivities of Dirigent Proteins in Arabidopsis and Schizandra Species Kim, Kye-Won; Moinuddin, Syed G. A.; Atwell, Kathleen M. Journal of Biological Chemistry, Vol. 287, Issue 41 https://doi.org/10.1074/jbc.M112.387423	journal	August 2012
9-Methoxy-6a,11a-dimethyl-6a,11a-dihydro-6H-1-benzofuro[3,2-c]chromen-3-ol fromDalbergia oliveri Deesamer, Sujittra; Chavasiri, Warinthorn; Chaichit, Narongsak Acta Crystallographica Section E Structure Reports Online, Vol. 65, Issue 10 https://doi.org/10.1107/S1600536809034485	journal	September 2009
Search and sequence analysis tools services from EMBL-EBI in 2022 Madeira, Fábio; Pearce, Matt; Tivey, Adrian R. N. Nucleic Acids Research, Vol. 50, Issue W1 https://doi.org/10.1093/nar/gkac240	journal	April 2022
Autodock Vina Adopts More Accurate Binding Poses but Autodock4 Forms Better Binding Affinity Nguyen, Nguyen Thanh; Nguyen, Trung Hai; Pham, T. Ngoc Han Journal of Chemical Information and Modeling, Vol. 60, Issue 1 https://doi.org/10.1021/acs.jcim.9b00778	journal	December 2019
Molecular cloning and biochemical characterization of isoflav-3-ene synthase, a key enzyme of the biosyntheses of (+)-pisatin and coumestrol Uchida, Kai; Aoki, Toshio; Suzuki, Hideyuki Plant Biotechnology, Vol. 37, Issue 3 https://doi.org/10.5511/plantbiotechnology.20.0421a	journal	September 2020
Purification and Characterization of S-Adenosyl-l-methionine:6a-Hydroxymaackiain 3-O-Methyltransferase from Pisum sativum Preisig, Carol L.; Matthews, David E.; VanEtten, Hans D. Plant Physiology, Vol. 91, Issue 2 https://doi.org/10.1104/pp.91.2.559	journal	October 1989
A genome-wide analysis of the flax (Linum usitatissimum L.) dirigent protein family: from gene identification and evolution to differential regulation Corbin, Cyrielle; Drouet, Samantha; Markulin, Lucija Plant Molecular Biology, Vol. 97, Issue 1-2 https://doi.org/10.1007/s11103-018-0725-x	journal	April 2018
The Missing Link in Leguminous Pterocarpan Biosynthesis is a Dirigent Domain-Containing Protein with Isoflavanol Dehydratase Activity Uchida, Kai; Akashi, Tomoyoshi; Aoki, Toshio Plant and Cell Physiology, Vol. 58, Issue 2 https://doi.org/10.1093/pcp/pcw213	journal	February 2017
Dirigent phenoxy radical coupling advances and challenges Davin, Laurence B.; Lewis, Norman G. Current Opinion in Biotechnology, Vol. 16, Issue 4, p. 398-406 https://doi.org/10.1016/j.copbio.2005.06.010	journal	August 2005
Towards automated crystallographic structure refinement with phenix.refine Afonine, Pavel V.; Grosse-Kunstleve, Ralf W.; Echols, Nathaniel Acta Crystallographica Section D Biological Crystallography, Vol. 68, Issue 4 https://doi.org/10.1107/S0907444912001308	journal	March 2012
Lignin primary structures and dirigent sites Davin, Laurence B; Lewis, Norman G Current Opinion in Biotechnology, Vol. 16, Issue 4, p. 407-415 https://doi.org/10.1016/j.copbio.2005.06.011	journal	August 2005
Regiochemical control of monolignol radical coupling: A new paradigm for lignin and lignan biosynthesis Gang, David R.; Costa, Michael A.; Fujita, Masayuki Chemistry & Biology, Vol. 6, Issue 3 https://doi.org/10.1016/S1074-5521(99)89006-1	journal	March 1999
How good are my data and what is the resolution? Evans, Philip R.; Murshudov, Garib N. Acta Crystallographica Section D Biological Crystallography, Vol. 69, Issue 7 https://doi.org/10.1107/S0907444913000061	journal	June 2013
Dirigent-mediated podophyllotoxin biosynthesis in Linum flavum and Podophyllum peltatum Xia, Zhi-Qiang; Costa, Michael A.; Proctor, John Phytochemistry, Vol. 55, Issue 6 https://doi.org/10.1016/S0031-9422(00)00242-9	journal	November 2000
Studies on the Constituents of Japanese and Chinese Crude Drugs. VII. On the Constituents of the Roots of Sophora subprostrata CHUN et T. CHEN, (2), and Sophora japonica L. (1). Shibata, Shoji; Nishikawa, Yoshihiro Chemical and Pharmaceutical Bulletin, Vol. 11, Issue 2 https://doi.org/10.1248/cpb.11.167	journal	January 1963
Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids Slade, Desmond; Ferreira, Daneel; Marais, Jannie P. J. Phytochemistry, Vol. 66, Issue 18 https://doi.org/10.1016/j.phytochem.2005.02.002	journal	September 2005
Caver Web 1.0: identification of tunnels and channels in proteins and analysis of ligand transport Stourac, Jan; Vavra, Ondrej; Kokkonen, Piia Nucleic Acids Research, Vol. 47, Issue W1 https://doi.org/10.1093/nar/gkz378	journal	May 2019
Stereoselective Bimolecular Phenoxy Radical Coupling by an Auxiliary (Dirigent) Protein Without an Active Center Davin, L. B.; Wang, H. -B.; Crowell, A. L. Science, Vol. 275, Issue 5298 https://doi.org/10.1126/science.275.5298.362	journal	January 1997
Inactivation of pea genes by RNAi supports the involvement of two similar O-methyltransferases in the biosynthesis of (+)-pisatin and of chiral intermediates with a configuration opposite that found in (+)-pisatin Kaimoyo, Evans; VanEtten, Hans D. Phytochemistry, Vol. 69, Issue 1 https://doi.org/10.1016/j.phytochem.2007.06.013	journal	January 2008
Dirigent gene editing of gossypol enantiomers for toxicity-depleted cotton seeds Lin, Jia-Ling; Fang, Xin; Li, Jian-Xu Nature Plants, Vol. 9, Issue 4 https://doi.org/10.1038/s41477-023-01376-2	journal	March 2023
XDS Kabsch, Wolfgang Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 2 https://doi.org/10.1107/S0907444909047337	journal	January 2010
Dirigent protein subfamily function and structure in terrestrial plant phenol metabolism Meng, Qingyan; Kim, Sung-Jin; Costa, Michael A. Methods in Enzymology, Vol. 683, p. 101-150 https://doi.org/10.1016/bs.mie.2023.02.025	book	April 2023
Time-Dependent Density Functional Theory for Calculating Origin-Independent Optical Rotation and Rotatory Strength Tensors Autschbach, Jochen ChemPhysChem, Vol. 12, Issue 17 https://doi.org/10.1002/cphc.201100225	journal	September 2011
Inermin Associated with Pisatin in Peas Inoculated with the Fungus Monilinia fructicola Stoessl, A. Canadian Journal of Biochemistry, Vol. 50, Issue 1 https://doi.org/10.1139/o72-011	journal	January 1972
Deciphering the Role of Phytoalexins in Plant-Microorganism Interactions and Human Health Jeandet, Philippe; Hébrard, Claire; Deville, Marie-Alice Molecules, Vol. 19, Issue 11 https://doi.org/10.3390/molecules191118033	journal	November 2014
Global indicators of X-ray data quality Weiss, Manfred S. Journal of Applied Crystallography, Vol. 34, Issue 2 https://doi.org/10.1107/S0021889800018227	journal	April 2001
Flavonoids and isoflavonoids of chemotaxonomic significance from Glycyrrhiza pallidiflora (Leguminosae) Kajiyama, K.; Hiraga, Yukio; Takahashi, Kunio Biochemical Systematics and Ecology, Vol. 21, Issue 8 https://doi.org/10.1016/0305-1978(93)90090-E	journal	December 1993
Dirigent domain-containing protein is part of the machinery required for formation of the lignin-based Casparian strip in the root Hosmani, P. S.; Kamiya, T.; Danku, J. Proceedings of the National Academy of Sciences, Vol. 110, Issue 35 https://doi.org/10.1073/pnas.1308412110	journal	August 2013
A dirigent protein complex directs lignin polymerization and assembly of the root diffusion barrier Gao, Yi-Qun; Huang, Jin-Quan; Reyt, Guilhem Science, Vol. 382, Issue 6669 https://doi.org/10.1126/science.adi5032	journal	October 2023
ProteinsPlus: a comprehensive collection of web-based molecular modeling tools Schöning-Stierand, Katrin; Diedrich, Konrad; Ehrt, Christiane Nucleic Acids Research, Vol. 50, Issue W1 https://doi.org/10.1093/nar/gkac305	journal	April 2022
CASTp 3.0: computed atlas of surface topography of proteins Tian, Wei; Chen, Chang; Lei, Xue Nucleic Acids Research, Vol. 46, Issue W1 https://doi.org/10.1093/nar/gky473	journal	June 2018
Kinetic Study of Coniferyl Alcohol Radical Binding to the (+)-Pinoresinol Forming Dirigent Protein ^† Halls, Steven C.; Davin, Laurence B.; Kramer, David M. Biochemistry, Vol. 43, Issue 9 https://doi.org/10.1021/bi035959o	journal	March 2004
Maackiain is a novel antiallergic compound that suppresses transcriptional upregulation of the histamine H₁ receptor and interleukin‐4 genes Mizuguchi, Hiroyuki; Nariai, Yuki; Kato, Shuhei Pharmacology Research & Perspectives, Vol. 3, Issue 5 https://doi.org/10.1002/prp2.166	journal	August 2015
Non-host disease resistance response in pea (Pisum sativum) pods: Biochemical function of DRR206 and phytoalexin pathway localization Seneviratne, Herana Kamal; Dalisay, Doralyn S.; Kim, Kye-Won Phytochemistry, Vol. 113 https://doi.org/10.1016/j.phytochem.2014.10.013	journal	May 2015
Dirigent proteins in conifer defense II: Extended gene discovery, phylogeny, and constitutive and stress-induced gene expression in spruce (Picea spp.)☆ Ralph, Steven G.; Jancsik, Sharon; Bohlmann, Jörg Phytochemistry, Vol. 68, Issue 14 https://doi.org/10.1016/j.phytochem.2007.04.042	journal	July 2007
MolProbity : all-atom structure validation for macromolecular crystallography Chen, Vincent B.; Arendall, W. Bryan; Headd, Jeffrey J. Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 1 https://doi.org/10.1107/S0907444909042073	journal	December 2009
Continuum solvation models: A new approach to the problem of solute’s charge distribution and cavity boundaries Mennucci, Benedetta; Tomasi, Jacopo The Journal of Chemical Physics, Vol. 106, Issue 12 https://doi.org/10.1063/1.473558	journal	March 1997
Coot model-building tools for molecular graphics Emsley, Paul; Cowtan, Kevin Acta Crystallographica Section D Biological Crystallography, Vol. 60, Issue 12, p. 2126-2132 https://doi.org/10.1107/S0907444904019158	journal	November 2004
Ten years of probabilistic estimates of biocrystal solvent content: new insights via nonparametric kernel density estimate Weichenberger, Christian X.; Rupp, Bernhard Acta Crystallographica Section D Biological Crystallography, Vol. 70, Issue 6 https://doi.org/10.1107/S1399004714005550	journal	May 2014
Studies on Phytoalexins. V. The Structure of Pisatin from Pisum sativum L. Perrin, Dawn R.; Bottomley, W. Journal of the American Chemical Society, Vol. 84, Issue 10 https://doi.org/10.1021/ja00869a030	journal	May 1962
Stereoselective coupling of hemigossypol to form (+)-gossypol in moco cotton is mediated by a dirigent protein Liu, Jinggao; Stipanovic, Robert D.; Bell, Alois A. Phytochemistry, Vol. 69, Issue 18 https://doi.org/10.1016/j.phytochem.2008.06.007	journal	December 2008
7-Hydroxy-4′,5′-methylenedioxypterocarpan hemihydrate Chen, Qing; Zhang, Qi-Long; Zhang, Yun-Qian Acta Crystallographica Section E Structure Reports Online, Vol. 63, Issue 12 https://doi.org/10.1107/S160053680705965X	journal	November 2007
UCSF ChimeraX: Meeting modern challenges in visualization and analysis: UCSF ChimeraX Visualization System Goddard, Thomas D.; Huang, Conrad C.; Meng, Elaine C. Protein Science, Vol. 27, Issue 1 https://doi.org/10.1002/pro.3235	journal	September 2017
Solvent content of protein crystals Matthews, B. W. Journal of Molecular Biology, Vol. 33, Issue 2 https://doi.org/10.1016/0022-2836(68)90205-2	journal	April 1968
Comprehensive transcriptome analysis of the highly complex Pisum sativum genome using next generation sequencing Franssen, Susanne U.; Shrestha, Roshan P.; Bräutigam, Andrea BMC Genomics, Vol. 12, Issue 1 https://doi.org/10.1186/1471-2164-12-227	journal	May 2011
Molecular Cloning of Isoflavone Reductase from Pea (Pisum sativum L): Evidence for a 3R-Isoflavanone Intermediate in (+)-Pisatin Biosynthesis Paiva, N. L.; Sun, Y. J.; Dixon, R. A. Archives of Biochemistry and Biophysics, Vol. 312, Issue 2 https://doi.org/10.1006/abbi.1994.1338	journal	August 1994
Total Syntheses of Biologically Active Pterocarpan, Isoflavan, and Isoflavanone from Dalbergia oliveri Singh, Dileep Kumar; Kim, Jinwoo; Sung, Jong‐Hyuk Bulletin of the Korean Chemical Society, Vol. 39, Issue 2 https://doi.org/10.1002/bkcs.11375	journal	January 2018
An introduction to data reduction: space-group determination, scaling and intensity statistics Evans, Philip R. Acta Crystallographica Section D Biological Crystallography, Vol. 67, Issue 4 https://doi.org/10.1107/S090744491003982X	journal	March 2011
Trimeric Structure of (+)-Pinoresinol-forming Dirigent Protein at 1.95 Å Resolution with Three Isolated Active Sites Kim, Kye-Won; Smith, Clyde A.; Daily, Michael D. Journal of Biological Chemistry, Vol. 290, Issue 3 https://doi.org/10.1074/jbc.M114.611780	journal	November 2014
AutoDock Vina 1.2.0: New Docking Methods, Expanded Force Field, and Python Bindings Eberhardt, Jerome; Santos-Martins, Diogo; Tillack, Andreas F. Journal of Chemical Information and Modeling, Vol. 61, Issue 8 https://doi.org/10.1021/acs.jcim.1c00203	journal	July 2021
Notizen: Phytoalexin Production by Flowers of Garden Pea (Pisum sativum ) Ingham, John L. Zeitschrift für Naturforschung C, Vol. 34, Issue 3-4 https://doi.org/10.1515/znc-1979-3-425	journal	April 1979
Isolation of a Phytoalexin from Pisum sativum L. Cruickshank, I. A. M.; Perrin, Dawn R. Nature, Vol. 187, Issue 4739 https://doi.org/10.1038/187799b0	journal	August 1960
Dirigent Protein-Mediated Lignan and Cyanogenic Glucoside Formation in Flax Seed: Integrated Omics and MALDI Mass Spectrometry Imaging Dalisay, Doralyn S.; Kim, Kye Won; Lee, Choonseok Journal of Natural Products, Vol. 78, Issue 6 https://doi.org/10.1021/acs.jnatprod.5b00023	journal	May 2015
Studies on the late steps of (+) pisatin biosynthesis: Evidence for (−) enantiomeric intermediates Dicenzo, G.; Vanetten, H. Phytochemistry, Vol. 67, Issue 7 https://doi.org/10.1016/j.phytochem.2005.12.027	journal	April 2006
Data processing and analysis with the autoPROC toolbox Vonrhein, Clemens; Flensburg, Claus; Keller, Peter Acta Crystallographica Section D Biological Crystallography, Vol. 67, Issue 4 https://doi.org/10.1107/S0907444911007773	journal	March 2011
Relationship of dirigent protein and 18s RNA transcript localization to heartwood formation in western red cedar Patten, Ann M.; Davin, Laurence B.; Lewis, Norman G. Phytochemistry, Vol. 69, Issue 18 https://doi.org/10.1016/j.phytochem.2008.06.020	journal	December 2008
Dirigent Protein Mode of Action Revealed by the Crystal Structure of AtDIR6 Gasper, Raphael; Effenberger, Isabelle; Kolesinski, Piotr Plant Physiology, Vol. 172, Issue 4 https://doi.org/10.1104/pp.16.01281	journal	October 2016
(+)-Pisatin biosynthesis: From (−) enantiomeric intermediates via an achiral 7,2′-dihydroxy-4′,5′-methylenedioxyisoflav-3-ene Celoy, Rhodesia M.; VanEtten, Hans D. Phytochemistry, Vol. 98 https://doi.org/10.1016/j.phytochem.2013.10.017	journal	February 2014
Avogadro: an advanced semantic chemical editor, visualization, and analysis platform Hanwell, Marcus D.; Curtis, Donald E.; Lonie, David C. Journal of Cheminformatics, Vol. 4, Issue 1 https://doi.org/10.1186/1758-2946-4-17	journal	August 2012
MOLREP an Automated Program for Molecular Replacement Vagin, A.; Teplyakov, A. Journal of Applied Crystallography, Vol. 30, Issue 6, p. 1022-1025 https://doi.org/10.1107/S0021889897006766	journal	December 1997
SpecDis: Quantifying the Comparison of Calculated and Experimental Electronic Circular Dichroism Spectra: UV AND ECD EVALUATION WITH SPECDIS Bruhn, Torsten; Schaumlöffel, Anu; Hemberger, Yasmin Chirality, Vol. 25, Issue 4 https://doi.org/10.1002/chir.22138	journal	March 2013
Secondary and Quaternary Structures of the (+)-Pinoresinol-Forming Dirigent Protein ^† Halls, Steven C.; Lewis, Norman G. Biochemistry, Vol. 41, Issue 30 https://doi.org/10.1021/bi0259709	journal	July 2002
Matthews coefficient probabilities: Improved estimates for unit cell contents of proteins, DNA, and protein-nucleic acid complex crystals Kantardjieff, Katherine A.; Rupp, Bernhard Protein Science, Vol. 12, Issue 9 https://doi.org/10.1110/ps.0350503	journal	September 2003
The Synthesis, Structure, and Anticancer Activity of cis- and trans-4‘,7-Dihydroxyisoflavan-4-ols Wähälä, Kristiina; Koskimies, Jorma K.; Mesilaakso, Markku The Journal of Organic Chemistry, Vol. 62, Issue 22 https://doi.org/10.1021/jo970892u	journal	October 1997
A deliberate approach to screening for initial crystallization conditions of biological macromolecules Luft, Joseph R.; Collins, Robert J.; Fehrman, Nancy A. Journal of Structural Biology, Vol. 142, Issue 1 https://doi.org/10.1016/S1047-8477(03)00048-0	journal	April 2003
Studies on Prytoalexins III. The Isolation, Assay, and General Properties of a Phytoalexin From Pisum Sativum L. Cruiokshank, Iam; R. Perrin, Dawn Australian Journal of Biological Sciences, Vol. 14, Issue 3 https://doi.org/10.1071/BI9610336	journal	January 1961
Role of an isoflav-3-ene in the biosynthesis of pterocarpan, isoflavan amd coumestan metabolites of sativa Martin, Maria; Dewick, Paul M. Tetrahedron Letters, Vol. 19, Issue 26 https://doi.org/10.1016/S0040-4039(01)91531-X	journal	January 1978
Dirigent Proteins from Cotton ( Gossypium sp.) for the Atropselective Synthesis of Gossypol Effenberger, Isabelle; Zhang, Bin; Li, Ling Angewandte Chemie International Edition, Vol. 54, Issue 49 https://doi.org/10.1002/anie.201507543	journal	October 2015

Similar Records

Stereochemical course of the reaction catalyzed by the pyridoxal phosphate-dependent enzyme 1-aminocyclopropane-1-carboxylate synthase

Journal Article · Sun Dec 01 00:00:00 EST 1985 · Proc. Natl. Acad. Sci. U.S.A.; (United States) · OSTI ID:2335877

Ramalingam, K; Lee, K M; Woodard, R W; +2 more

Structural Basis for Dual Functionality of Isoflavonoid O-Methyltransferases in the Evolution of Plant Defense Responses

Journal Article · Tue Jul 10 00:00:00 EDT 2007 · Submitted to Plant Cell · OSTI ID:2335877

Liu, C -J; Deavours, B E; Richard, S B; +5 more

Structural Basis for Dual Functionality of Isoflavonoid O-Methyltransferases in the Evolution of Plant Defense Responses

Journal Article · Sun Jan 01 00:00:00 EST 2006 · The Plant Cell · OSTI ID:2335877

Liu, C; Deavours, B; Richard, S; +5 more

Related Subjects

59 BASIC BIOLOGICAL SCIENCES
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
dirigent proteins
Leguminosae
pea
Pisum sativum
licorice
Glycyrrhiza sp.
Bolusanthus speciosus
pterocarpans
phytoalexins
stereoselectivity

Title: Dirigent isoflavene-forming PsPTS2: 3D structure, stereochemical, and kinetic characterization comparison with pterocarpan-forming PsPTS1 homolog in pea

Citation Formats

References (77)

Similar Records

Related Subjects