Review
Chemistry, Multidisciplinary
Baptiste Legrand, Ludovic T. Maillard
Summary: This review provides a comprehensive overview of the developments of gamma-peptide foldamers containing alpha,beta-unsaturated gamma-amino acids, including examples of applications for health, catalysis, and materials science. It highlights the divergent conformational behaviors and potential applications of these foldamers.
Article
Chemistry, Multidisciplinary
Saikat Pahan, Sanjit Dey, Gijo George, Souvik Panda Mahapatra, DRGKoppalu R. Puneeth Kumar, Hosahudya. N. Gopi
Summary: In this study, chiral beta-double helices constructed from specific amino acids were observed in both single crystals and in solution. These structures can transport ions across membranes, suggesting their potential applications in designing functional foldamers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Arnaud Delbrassinne, Boris Junior Takam Mba, Laurent Collard, Raphael Robiette
Summary: An efficient protocol for synthesizing enolizable alpha-substituted beta, gamma-unsaturated aldehydes is reported. The protocol involves two steps, epoxidation and Meinwald rearrangement, resulting in the one-carbon homologation of alpha, beta-unsaturated aldehydes, enabling the insertion of a CHR unit.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Srayoshi Roy Chowdhury, Debasish Haldar
Summary: We have designed and synthesized a gamma-turn mimetic that can change its conformation and optoelectronic properties through external stimuli. The compound selectively recognizes Cu(II) and exhibits a distinct color change. Based on this recognition event, we have developed a combinatorial multiple logic gate.
Article
Chemistry, Multidisciplinary
Liang Tang, Yicong Luo, Cheng Sheng, Fang Xie, Wanbin Zhang
Summary: This article reports the efficient kinetic resolution of gamma-substituted alpha,beta-unsaturated gamma-lactams via a Cu-catalyzed asymmetric boron conjugate addition, which leads to the synthesis of chiral beta-hydroxy-gamma-lactams with beta,gamma-stereogenic carbon centers. The method is successful with a wide range of substrates and exhibits versatile transformations and synthetic utility in biologically active molecules. Mechanistic studies indicate that a Lewis acid Cu-I-catalyzed mechanism is the likely pathway in the catalytic reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Chao-Shen Zhang, Lei Bao, Kun-Quan Chen, Zhi-Xiang Wang, Xiang-Yu Chen
Summary: A simple NaI-involved photoinduced deaminative alkenylation was proposed for the synthesis of beta,gamma-unsaturated esters without the need for photocatalysts and additives. Density functional theory study revealed that the electrostatic interaction of NaI with Katritzky salts is crucial in forming the photoactive electron donor-acceptor complex.
Article
Chemistry, Organic
Chunxiang Pan, Chunhui Yang, Kangkui Li, Keyang Zhang, Yuanbin Zhu, Shiyuan Wu, Yongyun Zhou, Baomin Fan
Summary: An efficient, catalyst/photocatalyst-free, and cost-effective methodology has been developed for the synthesis of beta,gamma-unsaturated nitriles from alpha,beta-unsaturated carboxylic acids. The reaction proceeded in an environmentally benign atmosphere of blue light-emitting diode irradiation with K2CO3 and water at room temperature, showing high yields (up to 83%) with a wide range of substrates.
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, Organic
Lu Zhao, En-Ze Yao, Guo-Li Chai, Shi-Yu Ma, Junbiao Chang
Summary: In this study, the (R)-3,3'-Br-2-BINOL-catalyzed enantioselective conjugate addition of organic boronic acids to beta,gamma-unsaturated alpha-ketoesters was achieved with moderate to high yields and moderate to excellent enantioselectivities (up to 99% ee). The catalytic system displayed characteristics of mild reaction conditions, high efficiency, and tolerance to alkenylboronic acids and heteroarylboronic acids.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Yu Yan, Wen-Cong Li, He Meng, Shufeng Chen, Jialin Ming, Tamio Hayashi
Summary: Racemic gamma-substituted alpha,beta-unsaturated gamma-lactams rac-1 reacted with arylboron reagents 2 in the presence of a chiral diene L1a-rhodium catalyst under basic conditions (3.0 equiv of NEt3) to give beta,gamma-disubstituted trans-gamma-lactams 3 with high diastereo- and enantioselectivity. This highly efficient dynamic kinetic resolution was achieved by fast racemization of 1 followed by kinetic resolution with the chiral rhodium catalyst. The synthetic utility of the method was demonstrated by the synthesis of key intermediates to biologically active compounds.
Article
Biochemistry & Molecular Biology
Alexander V. Aksenov, Dmitrii A. Aksenov, Igor A. Kurenkov, Alexander V. Leontiev, Nicolai A. Aksenov
Summary: A two-step procedure for synthesizing novel, highly functionalized 5-hydroxy 3-pyrrolin-2-ones is described. This involves an addition reaction between KCN and corresponding chalcones, followed by ring condensation of the obtained β-cyano ketones with het(aryl)aldehydes under basic conditions. The resulting compounds, 3,5-di-aryl/heteroaryl-4-benzyl substituted α,β-unsaturated γ-hydroxy butyrolactams, are of significant interest in synthetic organic and medicinal chemistry.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Review
Multidisciplinary Sciences
Ruixian Deng, Tian-Jiao Han, Xiang Gao, Yuan-Fu Yang, Guang-Jian Mei
Summary: beta,gamma-Unsaturated alpha-ketoesters are versatile organic synthons in catalytic asymmetric transformations. The highly efficient creation of stereogenic centers with excellent enantioselectivity is achieved through the bidentate coordination of their unique 1,2-dicarbonyl motif to chiral messengers. Various reaction modes of beta,gamma-Unsaturated alpha-ketoesters involving multiple reaction sites have been developed in the past five years. This review provides an updated overview for chemists working in this field, facilitating their discoveries in asymmetric catalysis, natural products synthesis, and drug development.
Article
Chemistry, Multidisciplinary
Sanliang Li, Qiaoyu Chen, Junfeng Yang, Junliang Zhang
Summary: In this study, an efficient asymmetric gamma-arylation method for constructing chiral quaternary arylated butenolide was reported. The method showed high selectivity, good functional group tolerance, and excellent enantioselectivity. Additionally, it allowed for the facile construction of tricyclic tetrahydroindolines and tetrahydroisoquinolinones in one step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Sebastian Heindl, Margaux Riomet, Jan Matyasovsky, Miran Lemmerer, Nicolas Malzer, Nuno Maulide
Summary: A chemoselective and robust protocol for the gamma-oxidation of beta,gamma-unsaturated amides has been developed, showcasing the synthetic utility of the products obtained through radical cyclisation reactions and oxidation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Zubao Gan, Deyun Cui, Hongyun Zhang, Ying Feng, Liying Huang, Yingying Gui, Lu Gao, Zhenlei Song
Summary: The Hosomi-Sakurai allylation of allylsilanes with beta,gamma-unsaturated alpha-ketoesters has been successfully catalyzed by (Ph3C)[BPh((F))(4)] to afford gamma,gamma-disubstituted alpha-ketoesters in high yields and excellent chemoselectivity. Preliminary mechanistic studies indicate that the trityl cation is the major contributor to the catalysis, with the silyl cation playing a minor role.
Article
Multidisciplinary Sciences
Zachary P. Gates, Alexander A. Vinogradov, Anthony J. Quartararo, Anupam Bandyopadhyay, Zi-Ning Choo, Ethan D. Evans, Kathryn H. Halloran, Alexander J. Mijalis, Surin K. Mong, Mark D. Simon, Eric A. Standley, Evan D. Styduhar, Sarah Z. Tasker, Faycal Touti, Jessica M. Weber, Jessica L. Wilson, Timothy F. Jamison, Bradley L. Pentelute
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2018)
Article
Biochemistry & Molecular Biology
Faycal Touti, Zachary P. Gates, Anupam Bandyopdhyay, Guillaume Lautrette, Bradley L. Pentelute
NATURE CHEMICAL BIOLOGY
(2019)
Correction
Biochemistry & Molecular Biology
Faycal Touti, Zachary P. Gates, Anupam Bandyopadhyay, Guillaume Lautrette, Bradley L. Pentelute
NATURE CHEMICAL BIOLOGY
(2019)
Article
Radiology, Nuclear Medicine & Medical Imaging
Tolulope A. Aweda, Zumrut F. B. Muftuler, Adriana V. F. Massicano, Dhruval Gadhia, Kelly A. McCarthy, Stacy Queern, Anupam Bandyopadhyay, Jianmin Gao, Suzanne E. Lapi
CONTRAST MEDIA & MOLECULAR IMAGING
(2019)
Review
Biochemistry & Molecular Biology
Arnab Chowdhury, Saurav Chatterjee, Akumlong Pongen, Dhanjit Sarania, Nitesh Mani Tripathi, Anupam Bandyopadhyay
Summary: The site-selective bioconjugation methods for aromatic side chains (Trp, Tyr and His) have gained attention in therapeutic applications, highlighting recent developed strategies and applications. Metal-catalyzed and photocatalytic reactions are receiving more attention for bioconjugation, though practical operation is still under development. The review examines the future perspective of protein and peptide conjugations for therapeutic applications and challenges.
PROTEIN AND PEPTIDE LETTERS
(2021)
Review
Biochemistry & Molecular Biology
Arnab Chowdhury, Anupam Bandyopadhyay
Summary: Natural cyclic peptide scaffolds are important in drug discovery due to their chemical diversity, structural integrity, stability, and compatibility. Some of these scaffolds show activity against drug-resistant tuberculosis, making them potential candidates for drug development. This review examines the biological origin, isolation, synthesis, and mechanisms of action of these cyclic peptides against tuberculosis.
CURRENT PROTEIN & PEPTIDE SCIENCE
(2022)
Review
Chemistry, Medicinal
Nitesh Mani Tripathi, Anupam Bandyopadhyay
Summary: High-throughput virtual screening (HTVS) is an important biopharmaceutical technology that utilizes computational algorithms to discover biologically active compounds from large compound libraries, saving resources and time in drug discovery. Peptide-based drug discovery has gained momentum in recent years, highlighting the need for a high-fidelity HTVS platform for chemically versatile peptide libraries.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Saurav Chatterjee, Anupam Bandyopadhyay
Summary: The use of peptide drugs for controlling certain diseases has significantly increased in the past two decades. A generic formulation is considered as a solution to meet market demands. Ganirelix, a leading peptide active pharmaceutical ingredient primarily used as a gonadotropin-releasing hormone antagonist, has a potential market value worldwide. However, its generic formulation requires detailed impurity profiles and similarity to a reference-listed drug.
JOURNAL OF PEPTIDE SCIENCE
(2023)
Article
Chemistry, Organic
Saurav Chatterjee, Anupam Bandyopadhyay
Summary: This study demonstrates the suitability and efficiency of thiol-ene radical click chemistry for installing functionally versatile boronic acid derivatives on various bioactive peptides. The method is operationally simple and can be adapted for a wide range of applications with boronic acid-modified peptides, including cyclization, conjugation, and functional group alteration.
Article
Chemistry, Organic
Arnab Chowdhury, Vinod Gour, Basab Kanti Das, Saurav Chatterjee, Anupam Bandyopadhyay
Summary: We have developed a highly efficient disulfide-driven peptide macrocyclization method that can be completed in 15 minutes on a solid support. This method uses persulfate as a crucial additive in iodine-mediated oxidative cyclization, eliminating the side products commonly seen in classical iodine-mediated peptide cyclization. It is a simple and convenient approach for cyclizing various peptides, from small to lengthier ones, that contain popular cysteine building blocks.
Article
Biochemistry & Molecular Biology
Jyotsna Bhatt Mitra, Saurav Chatterjee, Anuj Kumar, Anupam Bandyopadhyay, Archana Mukherjee
Summary: Developing potent and novel bacterial imaging agents remains a challenge due to bacterial resistance. This study investigates the use of covalent probes and non-covalent interactions to improve bacterial infection imaging. Tc-99m-UBI (29-41)-2-APBA demonstrates enhanced uptake and higher target-to-non-target ratio in a mouse model.
RSC MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Saurav Chatterjee, Nitesh Mani Tripathi, Anupam Bandyopadhyay
Summary: Boron was previously misunderstood as toxic to animals, hindering the development of boron-containing drugs, but with the WHO declaring boron as a 'probable essential element' for humans, the modern applications of boronic acid derivatives in biomedicine have become more attractive. The approval of five boronic acid-containing drugs by the FDA has greatly impacted the use of boron in various fields.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Ashim Paul, Sourav Kumar, Sujan Kalita, Sourav Kalita, Dibakar Sarkar, Anirban Bhunia, Anupam Bandyopadhyay, Amal Chandra Mondal, Bhubaneswar Mandal
Summary: Synthetic antibodies show great promise in combating diseases and biomedical applications, but designing a therapeutic synthetic antibody to prevent amyloid-beta aggregation remains challenging. A novel synthetic paratope, SP1, has been reported to prevent A beta aggregation, reverse amyloid fibrils, and reduce neurotoxicity in human cells. This new paratope engineering module may lead to cost-effective molecular probes for combating protein misfolding-related diseases.
Article
Chemistry, Multidisciplinary
Manisha Lamba, Avijit Goswami, Anupam Bandyopadhyay
Summary: Boron neutron capture therapy requires a high concentration of boron accumulation in neoplastic cells. Only BPA and BSH have been proven effective in clinical trials. Researchers have developed a variety of derivatives to make them more suitable for BNCT.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Saurav Chatterjee, Eric Anslyn, Anupam Bandyopadhyay
Summary: This article discusses the widespread applications of reversible click reactions in chemical biology, medicinal chemistry, biomedical devices, and material chemistry in recent years, with a focus on the reversible click chemistries of iminoboronate and salicylhydroxamic-boronate and their fundamental reactivities with various nucleophiles at different pH levels.
