Article
Biotechnology & Applied Microbiology
Mingfeng Cao, Vinh G. Tran, Jiansong Qin, Andrew Olson, Shekhar Mishra, John C. Schultz, Chunshuai Huang, Dongming Xie, Huimin Zhao
Summary: This study demonstrates the metabolic engineering of Rhodotorula toruloides to achieve high production of the plant-sourced polyketide triacetic acid lactone (TAL). By introducing relevant genes and optimizing metabolic pathways, TAL production was significantly increased. The findings highlight the potential of Rhodotorula toruloides as a host for the production of TAL and other polyketides from low-cost carbon sources.
BIOTECHNOLOGY AND BIOENGINEERING
(2022)
Article
Chemistry, Physical
Min Soo Kim, Dasol Choi, Jihyo Ha, Kyuhyeok Choi, Jae-Hyuk Yu, James A. Dumesic, George W. Huber
Summary: This study demonstrates a new route for the production of potassium sorbate from triacetic acid lactone. By hydrogenating TAL, dehydrating HMP, and conducting ring-opening hydrolysis of PSA, high-purity potassium sorbate can be obtained. The study shows that the highest yield occurs at low temperatures, and the experimental results agree with the reaction kinetics model. The synthesized potassium sorbate exhibits similar antimicrobial activities as commercial products.
Article
Chemistry, Organic
Zhi-Hao You, Sheng Zou, Ya-Li Song, Xue-Qing Song
Summary: An organocatalyzed asymmetric synthesis of fused butyrolactones has been established via a one-pot process. The reaction involves the formal [2 + 2 + 2] annulation between gamma-butenolides, methylene indolinones, and nitroolefins. The L tertleucine-derived bifunctional thiourea catalyst provides good yields (up to 95%) and excellent enantioselectivities (up to >99% ee).
Article
Chemistry, Analytical
Shuaizhen Zhou, Zia Fatma, Pu Xue, Shekhar Mishra, Mingfeng Cao, Huimin Zhao, Jonathan Sweedler
Summary: To meet the increasing need for high-throughput screening in metabolic engineering, a fast and information-rich screening method is required. Liquid extraction surface analysis coupled with mass spectrometry (LESA-MS) is an efficient approach that directly samples and introduces metabolites from a surface to MS. In this study, LESA-MS combined with an acoustic liquid handler and stable isotope-labeled internal standards, enabling absolute quantitation of target chemicals and high-throughput screening for microbial metabolites.
ANALYTICAL CHEMISTRY
(2023)
Article
Biotechnology & Applied Microbiology
Yangming Liu, Yuhan Jin, Peng Xu, Li Deng, Huan Liu, Fang Wang
Summary: Triacetic acid lactone (TAL) is an important platform chemical that acts as a bridge between biotransformation and chemical catalysis. Conventional extraction and conversion methods have limited the large-scale application of TAL due to environmental concerns and limited natural resources. This review summarizes the progress of TAL biomanufacturing using engineered microbes, including the construction of biosynthetic pathways, utilization of biomass and industrial waste as feedstocks, and the development of novel biosensors. Despite successful biosynthesis, there are challenges to economically viable TAL biomanufacturing, which are discussed along with potential strategies to improve techno-economic feasibility.
BIOCHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Organic
Fayang G. Qiu, Linping Wu, Yiming Guo
Summary: In this study, a highly diastereo- and enantioselective formal [4 + 2] cyclization was achieved through a tandem asymmetric Michael addition-intramolecular Henry reaction using dihydroquinine-based phase-transfer catalysis. This method allowed for the one-pot construction of compounds with four contiguous stereochemical centers and multiple functional groups in high yields, with excellent diastereo- and enantioselectivities.
Article
Biotechnology & Applied Microbiology
Yuta Matsuoka, Naofumi Fujie, Mariko Nakano, Ayumi Koshiba, Akihiko Kondo, Tsutomu Tanaka
Summary: This study demonstrates the production of value-added compound TAL from glucose using metabolic engineering techniques in an oleaginous yeast. Through the introduction of TAL-producing gene, manipulation of biosynthesis pathways, and optimization of carbon and nitrogen ratios, the production of TAL was significantly improved.
JOURNAL OF BIOSCIENCE AND BIOENGINEERING
(2023)
Article
Microbiology
Linjuan Feng, Junhao Xu, Cuifang Ye, Jucan Gao, Lei Huang, Zhinan Xu, Jiazhang Lian
Summary: In this study, an engineered Pichia pastoris strain was constructed for the production of Triacetic acid lactone (TAL). The TAL biosynthetic pathway was introduced by integrating a 2-pyrone synthase encoding gene from Gerbera hybrida (Gh2PS). The rate-limiting step of TAL synthesis was removed by introducing a mutant gene for acetyl-CoA carboxylase from S. cerevisiae (ScACC1*) and increasing the copy number of Gh2PS. Additionally, the phosphoketolase/phosphotransacetylase pathway (PK pathway) was introduced to enhance intracellular acetyl-CoA supply.
Article
Chemistry, Organic
Ramakrishna Samala, Manas K. Basu, K. Mukkanti
Summary: This article presents efforts towards synthesizing the kavalactone-based natural product penstyrylpyrone and related 4-OMe-2-pyrones with diverse substituents at the 3-, 5-, and 7-positions. Additionally, a simple approach for accessing 6-styrylpyrones through KHMDS-mediated regioselective aldol condensation of 2-pyrones is described, showing moderate substrate scope and good to high yields. The utility of this methodology is exemplified by the stereoselective construction of desmethoxyyangonin, asnipyrone A, and asnipyrone B.
TETRAHEDRON LETTERS
(2022)
Article
Biotechnology & Applied Microbiology
Ramkrishna Singh, Sarang S. Bhagwat, Mothi Bharath Viswanathan, Yoel R. Cortes-Pena, Kristen K. Eilts, Grace McDonough, Mingfeng Cao, Jeremy S. Guest, Huimin Zhao, Vijay Singh
Summary: In this study, the adsorption capacity of activated charcoal and a weak base resin for microbially produced triacetic acid lactone (TAL) was evaluated, and an adsorptive process for TAL recovery from fermentation broth was provided. A biorefinery producing TAL from sucrose was designed and evaluated through technoeconomic analysis.
BIOFUELS BIOPRODUCTS & BIOREFINING-BIOFPR
(2023)
Article
Chemistry, Organic
Yihong Wang, Claire M. M. Young, David B. B. Cordes, Alexandra M. Z. Slawin, Andrew D. D. Smith
Summary: The isothiourea-catalyzed formal [2+ 2] cycloaddition of C(1)-alkyl and C(1)-unsubstituted ammonium enolates with beta- and alpha,beta-substituted trifluoromethylenones has been developed. The reaction exhibited preferential [2 + 2]-cycloaddition over the alternative [4 + 2]-cycloaddition, resulting in beta-lactones with excellent diastereo- and enantioselectivity. The regioselectivity of the reaction was determined by the substituents on both reactants.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Matthew N. Grayson
Summary: Since 2004, the field of CPA catalysis has grown immensely, with Terada reporting the first example of CPA activation of aldehydes in 2008 and proposing a dual activation mode. DFT calculations have identified a lower-energy mechanism for this landmark reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Dattatraya N. Bhangare, Rohit G. Shinde, Pushpalata D. Pawar, Milind D. Nikalje, Mahendra N. Lokhande
Summary: This method utilizes Sc(OTf)(3) as a catalyst and (-)-menthol as a chiral auxiliary to achieve remarkable diastereoselectivity in the asymmetric aldol reaction. It offers mild reaction conditions, high yields, and excellent diastereoselectivity with a variety of substituted aromatic aldehydes. Sc(OTf)(3) demonstrates excellent diastereoselectivity at -45 degrees C under different reaction conditions.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Fangliang Li, Binli Wang, Xiao Chen, Hongjun Fan, Xueming Yang, Qing Guo
Summary: The study shows that the R-TiO2(100)-(1 x 1) surface exhibits high reactivity and selectivity for aldol condensation of unbranched aldehydes at room temperature. The low energy barriers for enolization and dehydration reactions, along with stable adsorption of intermediates, contribute to the surface's efficiency in forming crotonaldehyde. The exclusive selectivity of (E)-crotonaldehyde formation is attributed to the adsorption configuration of CH3CHO and surface structure of R-TiO2(100)(1 x 1).
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Organic
Swetha Sathyendran, Kesavan Muthu, Karthick Govindan, Nian-Qi Chen, Wei-Yu Lin, Gopal Chandru Senadi
Summary: A FeCl3-catalyzed decyanation of alpha-aminonitriles followed by a [4 + 2] annulation with terminal alkynes has been developed for the synthesis of 2,4-diaryl quinolines. The reaction showed good tolerance towards various aniline, aldehyde, and arylacetylene derivatives, providing moderate to good yields of the desired products. Control experiments suggested a nonradical pathway involving Povarov-type [4 + 2] annulation from an in situ generated iminium species. The method demonstrated the capability for gram-scale synthesis, continuous-flow process, and successful application with styrene.
Article
Chemistry, Organic
George A. Kraus, Umayangani K. Wanninayake, Jashaun Bottoms
TETRAHEDRON LETTERS
(2016)
Article
Biotechnology & Applied Microbiology
James Yu, Jenny Landberg, Farbod Shavarebi, Virginia Bilanchone, Adam Okerlund, Umayangani Wanninayake, Le Zhao, George Kraus, Suzanne Sandmeyer
BIOTECHNOLOGY AND BIOENGINEERING
(2018)
Article
Chemistry, Applied
S. P. Ratnayake, M. M. M. G. P. G. Mantilaka, C. Sandaruwan, D. Dahanayake, Y. Pivini Gunasekara, S. Jeyasakthy, N. M. Gurusinghe, U. K. Wanninayake, K. M. Nalin de Silva
Summary: A facile urea solution combustion method was used for synthesizing highly catalytic CeO2 nanostructures with varying properties under different thermal conditions. CeO2 synthesized at 800 degrees C exhibited superior catalytic performance compared to others, attributed to its unique nanomorphology. The synthesis of these CeO2 nanostructures represents a cost-effective and convenient abatement technique for carbon particulates in atmospheric pollution mitigation.
JOURNAL OF RARE EARTHS
(2021)
Article
Chemistry, Applied
K. A. U. Samanthi, Dhanushi T. Welideniya, Anjana Delpe Acharige, Sameera R. Samarakoon, Rajitha K. Rathnayaka, Madhavi de Silva, Shashika S. Perera, Colin Pieris, Umayangani K. Wanninayake, Adeesha Jayathilaka, Veranja Karunaratne, G. A. J. Amaratunga, Dinara S. Gunasekera
Summary: A novel cryocooled extraction method was developed to isolate linamarin from cassava root peel, resulting in the highest reported yield to date. The cytotoxicity of cassava crude extract was found to be higher than pure linamarin in the comprehensive cytotoxic assay using multiple cell lines, with results comparable to other studies in the literature.
NATURAL PRODUCT RESEARCH
(2021)
Article
Chemistry, Organic
Shashika Sevvandi Perera, Umayangani Kumari Wanninayake, Dhanushi Thathsara Welideniya, Adeesha Saseenda Jayathilaka, Anjana Delpe Acharige, Upamalika Samanthi, Shihan Shalinda Kaleel, Veranja Karunaratne, Gehan Amaratunga, Dinara Shashanka Gunasekera
Summary: The synthesis of levothyroxine sodium revolutionized the treatment of hypothyroidism, but the traditional synthetic route is outdated and lacks experimental data on intermediates, making laboratory and large-scale synthesis challenging. By modifying the synthesis steps and using modern reagents, higher overall yields were consistently achieved, providing a practical alternative method to synthesize levothyroxine sodium.
CURRENT ORGANIC SYNTHESIS
(2021)
Article
Biochemistry & Molecular Biology
Dhanushi T. Welideniya, Adeesha S. Jayathilaka, Anjana Delpe Acharige, K. A. U. Samanthi, Umayangani K. Wanninayake, Shashika S. Perera, Weranga Rajapaksha, Chamod C. Fernando, Madhavi Hewadikaram, Janani Buddhika, Pivini Gunasekara, Veranja Karunaratne, G. A. J. Amaratunga, Dinara S. Gunasekera
Summary: Beclomethasone dipropionate is a synthetic corticosteroid with anti-inflammatory, antipruritic, and anti-allergy properties. Current synthetic routes to this active pharmaceutical ingredient suffer from low and inconsistent yields, as well as the use of outdated reagents. This paper presents a practical and scalable approach to synthesize Beclomethasone dipropionate using a readily available steroidal intermediate.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
