Article
Chemistry, Organic
Hisanori Senboku, Yoshihito Minemura, Yuto Suzuki, Hidetoshi Matsuno, Mayu Takakuwa
Summary: Electrochemical reduction of N-Boc-alpha-aminosulfones in DMF led to reductive C-S bond cleavage, followed by fixation of carbon dioxide to give the corresponding N-Boc-alpha-amino acids in moderate to good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Petar Strbac, Anamarija Bris, Davor Margetic
Summary: In this study, the first representative of isoindoles containing guanidine functionality, N,N'-Di-Boc-2H-isoindole-2-carboxamidine, was synthesized and its cycloaddition reactivity was investigated. The results showed that the title compound exhibited higher reactivity and the substitution with fluorine or guanidine functionality did not alter the reactivity of isoindoles, which was in accordance with computational results.
Article
Chemistry, Organic
Manjeet Singh, Manish Kumar, Sachin A. Nalawade, DRGKoppalu R. Puneeth Kumar, Hosahudya N. Gopi
Summary: In this study, we demonstrate the spontaneous transformation of active esters of N-Boc protected E-alpha,beta-unsaturated gamma-amino acids into Z-alpha,beta-unsaturated gamma-lactams with concomitant E -> Z isomerization in the presence of a weak base. The absence of the base prevents cyclization. Our analysis shows that amide gamma-NH is crucial for both lactamization and E -> Z isomerization. This mild transformation provides a convenient method for synthesizing challenging alpha,beta-unsaturated gamma-lactams and contributes to our understanding of E -> Z isomerization of double bonds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Tomas Klunda, Michal Hricovini, Sergej Sestak, Juraj Kona, Monika Polakova
Summary: In this study, N-alkylated polyhydroxypyrrolidines were synthesized and tested as inhibitors of Golgi alpha-mannosidase II (GMIIb). The potency of the inhibitors varied depending on the alkyl chain length and capping functional group, with amidines showing the highest activity. Molecular docking and quantum mechanics calculations revealed the importance of alkyl chain length in the interactions with the target enzyme.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jairo Villalona, Peyton M. Higgins, Andrew R. Buller
Summary: Non-canonical amino acids (ncAAs) serve as useful materials for developing new medicines, materials, and bioactive probes. In this study, the beta-subunit of tryptophan synthase, TrpB, was engineered through directed evolution to improve its activity with diverse amine nucleophiles. Mechanistic analysis revealed hindrance to high yields due to product re-entry and subsequent decomposition. Additional equivalents of l-serine were able to inhibit product re-entry through kinetic competition, facilitating preparative scale synthesis. Several beta-substituted amino acids were synthesized using a variety of aryl amine nucleophiles, including demonstration on a gram scale. These amino acids represent an underexplored class of building blocks for chemical biology and medicinal chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jairo Villalona, Peyton M. Higgins, Andrew R. Buller
Summary: In this study, directed evolution was used to engineer the beta-subunit of tryptophan synthase for improved activity in the synthesis of beta-substituted amino acids. Mechanistic analysis revealed that product re-entry into the catalytic cycle and subsequent decomposition hindered high yields, but additional equivalents of l-serine could inhibit product re-entry and facilitate preparative scale synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Food Science & Technology
Oliver Brun, Claude Zoukimian, Barbara Oliveira-Mendes, Jerome Montnach, Benjamin Lauzier, Michel Ronjat, Remy Beroud, Frederic Lesage, Didier Boturyn, Michel De Waard
Summary: This study describes the chemical synthesis of a fluorescent-tagged alpha-bungarotoxin and demonstrates its binding properties on muscle nicotinic receptors using TE671 cells. The synthetic fluorescent alpha-bungarotoxin showed expected nanomolar affinity for the receptors and was able to label the cells.
Review
Engineering, Environmental
Xingchen Liu, Yangxia Han, Yang Shu, Jianhua Wang, Hongdeng Qiu
Summary: This review summarizes the current status and development direction of fluorescence sensors for 2,4,6-trinitrophenol (TNP), focusing on the sensing properties of different fluorescent materials towards TNP. The fluorescence strategy shows promising sensitivity and selectivity, rapid response speed, and simple operation, making it a potentially valuable method for TNP detection.
JOURNAL OF HAZARDOUS MATERIALS
(2022)
Article
Chemistry, Organic
Bing Zhou, Chen-Xi Ye, Eric Meggers
Summary: N-Boc-protected alpha-amino acids can be synthesized in two steps using linear or branched carboxylic acid feedstocks. The first step involves coupling the carboxylic acid with tert-butyl aminocarbonate (BocNHOH) to generate an azanyl ester (acyloxycarbamate) RCO(2)NHBoc. In the second step, this azanyl ester undergoes a stereocontrolled iron-catalyzed 1,3-nitrogen migration to generate the N-Boc-protected non-racemic alpha-amino acid. This method is versatile and allows for the synthesis of alpha-monosubstituted alpha-amino acids with different side chains, as well as alpha,alpha-disubstituted alpha-amino acids and alpha-deuterated alpha-amino acids.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Na-Ri-Mei Ao, Xue-Qing Zhu, Chun-Xin Zhao, Ya-Ru Gao, Yong-Qiang Wang
Summary: A novel photocatalyzed cross-dehydrogenative coupling reaction has been developed for the synthesis of C1-substituted tetrahydroisoquinolines from N-Boc-tetrahydroisoquinolines and alpha,beta-unsaturated ketones. This method provides access to benzo[a]-quinolizine-2-ones, the skeletons of natural products with diverse biological activities, using a low-load photocatalyst and inexpensive, less toxic oxidant.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Peiyuan Yao, James R. Marshall, Zefei Xu, Jesmine Lim, Simon J. Charnock, Dunming Zhu, Nicholas J. Turner
Summary: In this study, a new stereoselective biocatalytic synthesis method for N-substituted alpha-amino esters was reported, utilizing diverse metagenomic imine reductases. Both enantiomers of the target products were synthesized with high conversion and excellent enantioselectivity under mild reaction conditions. Furthermore, over 20 different preparative scale transformations were performed, demonstrating the scalability of this system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Bing-Ru Shao, Lei Shi, Yong-Gui Zhou
Summary: This feature article mainly introduces the research progress in catalytic asymmetric hydrogenation and transfer hydrogenation of arenes with O/N substituted groups, demonstrating the potential of this synthetic method in constructing important chiral cyclic skeletons.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Sha Hu, Jiale Wu, Zuolin Lu, Jiaqi Wang, Yuan Tao, Meifen Jiang, Fener Chen
Summary: A time-efficient method for obtaining unnatural α-amino esters through N-H insertion between anilines and alpha-alkyl and alpha-aryl-alpha-diazoacetates catalyzed by TfOH. The obtained α-amino esters can undergo various transformations and are useful for synthesizing pharmaceutically relevant molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ke Zhang, Xiao-Fei Liu, Wen-Zhen Zhang, Wei-Min Ren, Xiao-Bing Lu
Summary: The direct electrocarboxylation of N-acylimines with atmospheric CO2 has been achieved, providing substituted alpha-amino acids in high yields. The reaction is conducted efficiently using triethanolamine as an external reductant, and can be easily scaled up.
Article
Polymer Science
Rosa Catania, Ruggero Foralosso, Lampros Spanos, Emanuele Russo, Francesca Mastrotto, Pratik Gurnani, Kevin Butler, Huw Williams, Snow Stolnik, Giuseppe Mantovani
Summary: N-substituted maleimides are essential tools for the synthesis of bioconjugates and functional materials. This study presents three strategies for incorporating N-alkyl substituted maleimides into RAFT agents and demonstrates their ability to introduce a range of chemical functionality at the beta-position of polymer chains, resulting in alpha,beta,omega-functional RAFT polymers.
Article
Biochemistry & Molecular Biology
Nicholas McGregor, Mariya Morar, Thomas Hauch Fenger, Peter Stogios, Nicolas Lenfant, Victor Yin, Xiaohui Xu, Elena Evdokimova, Hong Cui, Bernard Henrissat, Alexei Savchenko, Harry Brumer
JOURNAL OF BIOLOGICAL CHEMISTRY
(2016)
Article
Plant Sciences
Nicholas McGregor, Victor Yin, Ching-Chieh Tung, Filip Van Petegem, Harry Brumer
Article
Microbiology
Melissa Robb, Joanne K. Hobbs, Shireen A. Woodiga, Sarah Shapiro-Ward, Michael D. L. Suits, Nicholas McGregor, Harry Brumer, Hasan Yesilkaya, Samantha J. King, Alisdair B. Boraston
Article
Chemistry, Physical
Olga V. Moroz, Pernille F. Jensen, Sean P. McDonald, Nicholas McGregor, Elena Blagova, Gerard Comamala, Dorotea R. Seura, Lars Anderson, Santhosh M. Vasu, Vasudeva P. Rao, Lars Giger, Trine Hoist Sorensen, Rune Nygaard Monrad, Allan Svendsen, Jens E. Nielsen, Bernard Henrissat, Gideon J. Davies, Harry Brumer, Kasper D. Rand, Keith S. Wilson
Article
Chemistry, Multidisciplinary
Nicholas McGregor, Christophe Pardin, W. G. Skene
AUSTRALIAN JOURNAL OF CHEMISTRY
(2011)
Article
Chemistry, Organic
Yanmei Dong, Andreanne Bolduc, Nicholas McGregor, W. G. Skene
Article
Chemistry, Organic
Etienne Knipping, Ivan Ulliel Roche, Stephane Dufresne, Nicholas McGregor, W. G. Skene
TETRAHEDRON LETTERS
(2011)
Article
Chemistry, Multidisciplinary
Sybrin P. Schroder, Casper de Boer, Nicholas G. S. McGregor, Rhianna J. Rowland, Olga Moroz, Elena Blagova, Jos Reijngoud, Mark Arentshorst, David Osborn, Marc D. Morant, Eric Abbate, Mary A. Stringer, Kristian B. R. M. Krogh, Lluis Raich, Carme Rovira, Jean-Guy Berrin, Gilles P. van Wezel, Arthur F. J. Ram, Bogdan Florea, Gijsbert A. van der Marel, Jeroen D. C. Codee, Keith S. Wilson, Liang Wu, Gideon J. Davies, Herman S. Overkleeft
ACS CENTRAL SCIENCE
(2019)
Article
Chemistry, Multidisciplinary
Nicholas G. S. McGregor, Marta Artola, Alba Nin-Hill, Daniel Linzel, Mireille Haon, Jos Reijngoud, Arthur Ram, Marie-Noelle Rosso, Gijsbert A. van der Marel, Jeroen D. C. Codee, Gilles P. van Wezel, Jean-Guy Berrin, Carme Rovira, Herman S. Overkleeft, Gideon J. Davies
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Biochemical Research Methods
Nicholas G. S. McGregor, Johan P. Turkenburg, Kristian B. R. Morkeberg Krogh, Jens Erik Nielsen, Marta Artola, Keith A. Stubbs, Herman S. Overkleeft, Gideon J. Davies
ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY
(2020)
Article
Chemistry, Multidisciplinary
Nicholas G. S. McGregor, Joan Coines, Valentina Borlandelli, Satoko Amaki, Marta Artola, Alba Nin-Hill, Daniel Linzel, Chihaya Yamada, Takatoshi Arakawa, Akihiro Ishiwata, Yukishige Ito, Gijsbert A. van der Marel, Jeroen D. C. Codee, Shinya Fushinobu, Herman S. Overkleeft, Carme Rovira, Gideon J. Davies
Summary: The discovery of zinc-dependent retaining glycoside hydrolases presents unresolved mechanistic questions, particularly the controversy surrounding the proposed mechanism involving a zinc-coordinated cysteine nucleophile and a thioglycosyl enzyme intermediate. A synthesized beta-l-arabinofuranosidase inhibitor reacts exclusively with the cysteine thiol catalytic nucleophiles of GH families 127 and 146, supporting further research into the breakdown of the thioglycosyl enzyme intermediate. X-ray crystal structures and simulations provide insight into the mechanisms of zinc-coordinated cysteine as the catalytic nucleophile and the energetics of this unique metalloenzyme clan.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Nicholas G. S. McGregor, Chi-Lin Kuo, Thomas J. M. Beenakker, Chun-Sing Wong, Wendy A. Offen, Zachary Armstrong, Bogdan Florea, Jeroen D. C. Codee, Herman S. Overkleeft, Johannes M. F. G. Aerts, Gideon J. Davies
Summary: Researchers have synthesized beta-manno-configured cyclophellitol and its analogues for detecting exo-beta-mannosidases. These probes selectively label exo-beta-mannosidases from different GH families and structural studies confirm their mechanism of action.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Casper de Boer, Nicholas G. S. McGregor, Evert Peterse, Sybrin P. Schroder, Bogdan I. Florea, Jianbing Jiang, Jos Reijngoud, Arthur F. J. Ram, Gilles P. van Wezel, Gijsbert A. van der Marel, Jeroen D. C. Codee, Herman S. Overkleeft, Gideon J. Davies
RSC CHEMICAL BIOLOGY
(2020)
Article
Biotechnology & Applied Microbiology
Mathieu Fanuel, Sona Garajova, David Ropartz, Nicholas McGregor, Harry Brumer, Helene Rogniaux, Jean-Guy Berrin
BIOTECHNOLOGY FOR BIOFUELS
(2017)