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Dynamic Conformational States Dictate Selectivity toward the Native Substrate in a Substrate-Permissive Acyltransferase.

Levsh O, Chiang YC, Tung CF, Noel JP, Wang Y, Weng JK
Biochemistry 55 6314-6326 (2016)
Related entries: 5kjt, 5kju, 5kjv, 5kjw

Cited: 23 times
EuropePMC logo PMID: 27805809

Abstract

Hydroxycinnamoyl-CoA:shikimate hydroxycinnamoyltransferase (HCT) is an essential acyltransferase that mediates flux through plant phenylpropanoid metabolism by catalyzing a reaction between p-coumaroyl-CoA and shikimate, yet it also exhibits broad substrate permissiveness in vitro. How do enzymes like HCT avoid functional derailment by cellular metabolites that qualify as non-native substrates? Here, we combine X-ray crystallography and molecular dynamics to reveal distinct dynamic modes of HCT under native and non-native catalysis. We find that essential electrostatic and hydrogen-bonding interactions between the ligand and active site residues, permitted by active site plasticity, are elicited more effectively by shikimate than by other non-native substrates. This work provides a structural basis for how dynamic conformational states of HCT favor native over non-native catalysis by reducing the number of futile encounters between the enzyme and shikimate.

Articles - 5kjs mentioned but not cited (4)

  1. Dynamic Conformational States Dictate Selectivity toward the Native Substrate in a Substrate-Permissive Acyltransferase. Levsh O, Chiang YC, Tung CF, Noel JP, Wang Y, Weng JK. Biochemistry 55 6314-6326 (2016)
  2. The physical basis and practical consequences of biological promiscuity. Copley SD. Phys Biol (2020)
  3. Crystal structure of barley agmatine coumaroyltransferase, an N-acyltransferase from the BAHD superfamily. Yamane M, Takenoya M, Yajima S, Sue M. Acta Crystallogr F Struct Biol Commun 76 590-596 (2020)
  4. Identification and in-silico characterization of taxadien-5α-ol-O-acetyltransferase (TDAT) gene in Corylus avellana L. Raeispour Shirazi M, Rahpeyma SA, Rashidi Monfared S, Zolala J, Lohrasbi-Nejad A. PLoS One 16 e0256704 (2021)


Reviews citing this publication (4)

  1. Promiscuity, impersonation and accommodation: evolution of plant specialized metabolism. Leong BJ, Last RL. Curr. Opin. Struct. Biol. 47 105-112 (2017)
  2. The Biological Activity Mechanism of Chlorogenic Acid and Its Applications in Food Industry: A Review. Wang L, Pan X, Jiang L, Chu Y, Gao S, Jiang X, Zhang Y, Chen Y, Luo S, Peng C. Front Nutr 9 943911 (2022)
  3. A Minireview on Temperature Dependent Protein Conformational Sampling. Dong M. Protein J 40 545-553 (2021)
  4. Family characteristics, phylogenetic reconstruction, and potential applications of the plant BAHD acyltransferase family. Xu D, Wang Z, Zhuang W, Wang T, Xie Y. Front Plant Sci 14 1218914 (2023)

Articles citing this publication (15)

  1. A phenol-enriched cuticle is ancestral to lignin evolution in land plants. Renault H, Alber A, Horst NA, Basilio Lopes A, Fich EA, Kriegshauser L, Wiedemann G, Ullmann P, Herrgott L, Erhardt M, Pineau E, Ehlting J, Schmitt M, Rose JK, Reski R, Werck-Reichhart D. Nat Commun 8 14713 (2017)
  2. COSY catalyses trans-cis isomerization and lactonization in the biosynthesis of coumarins. Vanholme R, Sundin L, Seetso KC, Kim H, Liu X, Li J, De Meester B, Hoengenaert L, Goeminne G, Morreel K, Haustraete J, Tsai HH, Schmidt W, Vanholme B, Ralph J, Boerjan W. Nat Plants 5 1066-1075 (2019)
  3. Function of the HYDROXYCINNAMOYL-CoA:SHIKIMATE HYDROXYCINNAMOYL TRANSFERASE is evolutionarily conserved in embryophytes. Kriegshauser L, Knosp S, Grienenberger E, Tatsumi K, Gütle DD, Sørensen I, Herrgott L, Zumsteg J, Rose JKC, Reski R, Werck-Reichhart D, Renault H. Plant Cell 33 1472-1491 (2021)
  4. Versatility in acyltransferase activity completes chicoric acid biosynthesis in purple coneflower. Fu R, Zhang P, Jin G, Wang L, Qi S, Cao Y, Martin C, Zhang Y. Nat Commun 12 1563 (2021)
  5. Targeting hydroxycinnamoyl CoA: shikimate hydroxycinnamoyl transferase for lignin modification in Brachypodium distachyon. Serrani-Yarce JC, Escamilla-Trevino L, Barros J, Gallego-Giraldo L, Pu Y, Ragauskas A, Dixon RA. Biotechnol Biofuels 14 50 (2021)
  6. Characterization and functional analysis of the Hydroxycinnamoyl-CoA: shikimate hydroxycinnamoyl transferase (HCT) gene family in poplar. Chao N, Qi Q, Li S, Ruan B, Jiang X, Gai Y. PeerJ 9 e10741 (2021)
  7. Characterization and structure-based protein engineering of a regiospecific saponin acetyltransferase from Astragalus membranaceus. Wang L, Jiang Z, Zhang J, Chen K, Zhang M, Wang Z, Wang B, Ye M, Qiao X. Nat Commun 14 5969 (2023)
  8. Emergence of a proton exchange-based isomerization and lactonization mechanism in the plant coumarin synthase COSY. Kim CY, Mitchell AJ, Kastner DW, Albright CE, Gutierrez MA, Glinkerman CM, Kulik HJ, Weng JK. Nat Commun 14 597 (2023)
  9. Genome-wide analysis of general phenylpropanoid and monolignol-specific metabolism genes in sugarcane. Jardim-Messeder D, Felix-Cordeiro T, Barzilai L, de Souza-Vieira Y, Galhego V, Bastos GA, Valente-Almeida G, Aiube YRA, Faria-Reis A, Corrêa RL, Sachetto-Martins G. Funct Integr Genomics 21 73-99 (2021)
  10. Independent evolution of rosmarinic acid biosynthesis in two sister families under the Lamiids clade of flowering plants. Levsh O, Pluskal T, Carballo V, Mitchell AJ, Weng JK. J. Biol. Chem. 294 15193-15205 (2019)
  11. Integrated Analysis of Metabolome and Transcriptome Revealed Different Regulatory Networks of Metabolic Flux in Tea Plants [Camellia sinensis (L.) O. Kuntze] with Varied Leaf Colors. Zhang Y, Wang L, Kong X, Chen Z, Zhong S, Li X, Shan R, You X, Wei K, Chen C. Int J Mol Sci 25 242 (2023)
  12. Phylogenomic analyses across land plants reveals motifs and coexpression patterns useful for functional prediction in the BAHD acyltransferase family. Kruse LH, Fehr B, Chobirko JD, Moghe GD. Front Plant Sci 14 1067613 (2023)
  13. Structural and Biochemical Insights Into Two BAHD Acyltransferases (AtSHT and AtSDT) Involved in Phenolamide Biosynthesis. Wang C, Li J, Ma M, Lin Z, Hu W, Lin W, Zhang P. Front Plant Sci 11 610118 (2020)
  14. Structural and Biochemical Studies of a Biocatalyst for the Enzymatic Production of Wax Esters. Petronikolou N, Nair SK. ACS Catal 8 6334-6344 (2018)
  15. Structural and dynamic basis of substrate permissiveness in hydroxycinnamoyltransferase (HCT). Chiang YC, Levsh O, Lam CK, Weng JK, Wang Y. PLoS Comput. Biol. 14 e1006511 (2018)


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