4.7 Article

Chemoenzymatic preparation of germacrene analogues

Journal

CHEMICAL COMMUNICATIONS
Volume 48, Issue 78, Pages 9702-9704

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c2cc35542f

Keywords

-

Funding

  1. United Kingdom's Biotechnology and Biological Sciences Research Council [BB/G003572/1, BB/H01683X/1]
  2. Cardiff University
  3. Biotechnology and Biological Sciences Research Council [BB/H01683X/1, BB/G003572/1] Funding Source: researchfish
  4. BBSRC [BB/G003572/1, BB/H01683X/1] Funding Source: UKRI

Ask authors/readers for more resources

A small library of novel germacrenes was generated using a combination of two plant enzymes, germacrene A synthase, and D synthase and modified farnesyl diphosphate (FDP) analogues. This chemoenzymatic approach allows the preparation of potentially valuable volatiles for biological studies.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.7
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Multidisciplinary Sciences

Emergence of terpene cyclization in Artemisia annua

Melissa Salmon, Caroline Laurendon, Maria Vardakou, Jitender Cheema, Marianne Defernez, Sol Green, Juan A. Faraldos, Paul E. O'Maille

NATURE COMMUNICATIONS (2015)

Article Biochemistry & Molecular Biology

Discovery of germacrene A synthases in Barnadesia spinosa: The first committed step in sesquiterpene lactone biosynthesis in the basal member of the Asteraceae

Trinh-Don Nguyen, Juan A. Faraldos, Maria Vardakou, Melissa Salmon, Paul E. O'Maille, Dae-Kyun Ro

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS (2016)

Article Biochemistry & Molecular Biology

Probing the Role of Active Site Water in the Sesquiterpene Cyclization Reaction Catalyzed by Aristolochene Synthase

Mengbin Chen, Wayne K. W. Chou, Naeemah Al-Lami, Juan A. Faraldos, Rudolf K. Allemann, David E. Cane, David W. Christianson

BIOCHEMISTRY (2016)

Review Biochemistry & Molecular Biology

REVIEW: Epistasis and dominance in the emergence of catalytic function as exemplified by the evolution of plant terpene synthases

Jitender Cheema, Juan A. Faraldos, Paul E. O'Maille

PLANT SCIENCE (2017)

Article Biochemistry & Molecular Biology

Rational engineering of plasticity residues of sesquiterpene synthases from Artemisia annua: product specificity and catalytic efficiency

Jian-Xu Li, Xin Fang, Qin Zhao, Ju-Xin Ruan, Chang-Qing Yang, Ling-Jian Wang, David J. Miller, Juan A. Faraldos, Rudolf K. Allemann, Xiao-Ya Chen, Peng Zhang

BIOCHEMICAL JOURNAL (2013)

Article Biochemistry & Molecular Biology

Mechanistic Insights from the Binding of Substrate and Carbocation Intermediate Analogues to Aristolochene Synthase

Mengbin Chen, Naeemah Al-lami, Marine Janvier, Edward L. D'Antonio, Juan A. Faraldos, David E. Cane, Rudolf K. Allemann, David W. Christianson

BIOCHEMISTRY (2013)

Article Chemistry, Multidisciplinary

Chemoenzymatic synthesis of the alarm pheromone (+)-verbenone from geranyl diphosphate

Zulfa Yoosuf-Aly, Juan A. Faraldos, David J. Miller, Rudolf K. Allemann

CHEMICAL COMMUNICATIONS (2012)

Article Chemistry, Organic

Alternative Synthesis of the Colorado Potato Beetle Pheromone

Juan A. Faraldos, Robert M. Coates, Jose-Luis Giner

JOURNAL OF ORGANIC CHEMISTRY (2013)

Article Chemistry, Multidisciplinary

A 1,6-Ring Closure Mechanism for (+)-δ-Cadinene Synthase?

Juan A. Faraldos, David J. Miller, Veronica Gonzalez, Zulfa Yoosuf-Aly, Oscar Cascon, Amang Li, Rudolf K. Allemann

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Multidisciplinary

Probing the Mechanism of 1,4-Conjugate Elimination Reactions Catalyzed by Terpene Synthases

Juan A. Faraldos, Veronica Gonzalez, Amang Li, Fanglei Yu, Mustafa Koeksal, David W. Christianson, Rudolf K. Allemann

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Multidisciplinary

Evolutionary and Mechanistic Insights from the Reconstruction of α-Humulene Synthases from a Modern (+)-Germacrene A Synthase

Veronica Gonzalez, Sabrina Touchet, Daniel J. Grundy, Juan A. Faraldos, Rudolf K. Allemann

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Multidisciplinary Sciences

Variation in Capsidiol Sensitivity between Phytophthora infestans and Phytophthora capsici Is Consistent with Their Host Range

Artemis Giannakopoulou, Sebastian Schornack, Tolga O. Bozkurt, Dave Haart, Dae-Kyun Ro, Juan A. Faraldos, Sophien Kamoun, Paul E. O'Maille

PLOS ONE (2014)

Article Chemistry, Multidisciplinary

An Efficient Chemoenzymatic Synthesis of Dihydroartemisinic Aldehyde

Melodi Demiray, Xiaoping Tang, Thomas Wirth, Juan A. Faraldos, Rudolf K. Allemann

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Multidisciplinary Sciences

Comparative analysis and validation of the malachite green assay for the high throughput biochemical characterization of terpene synthases

Maria Vardakou, Melissa Salmon, Juan A. Faraldos, Paul E. O'Maille

METHODSX (2014)

Review Chemistry, Multidisciplinary

Trap suppression in ordered organic photovoltaic heterojunctions

Dan He, Yawen Li, Fuwen Zhao, Yuze Lin

Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.

CHEMICAL COMMUNICATIONS (2024)

Review Chemistry, Multidisciplinary

Controversial mechanism of simultaneous photocatalysis and Fenton-based processes: additional effect or synergy?

Olivier Monfort, Arshitha Madhusudhan, Martin Motola

Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Polymerization of monomer aggregates for tailoring and patterning water wettability

Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna

Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Pd/Brønsted acid catalysed intramolecular N-allylation of indoles and pyrroles with alkynes for the synthesis of N-fused heterocycles

Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi

Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Rh(III)-catalyzed selective mono- and dual-functionalization/cyclization of 1-aryl-5-aminopyrazoles with iodonium ylides

Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang

Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Modified minimal-size fragments of heparan sulfate as inhibitors of endosulfatase-2 (Sulf-2)

Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell

Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Reductive cyclodimerization of chalcones: exploring the self-adaptability of galvanostatic electrosynthesis

Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini

Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Rh(III)-catalyzed oxidative [4+2] annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols

Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar

Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

PbTeB4O9: a lead tellurium borate with unprecedented fundamental building block [B4O10] and large birefringence

Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan

Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Wafer-scale synthesis of two-dimensional ultrathin films

Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal

Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.

CHEMICAL COMMUNICATIONS (2024)

Article Chemistry, Multidisciplinary

Precise design of copolymer-conjugated nanocatalysts for active electron transfer

Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi

Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.

CHEMICAL COMMUNICATIONS (2024)