Review
Chemistry, Medicinal
Michal G. Nowak, Andrzej S. Skwarecki, Maria J. Milewska
Summary: The structures of many antibacterial, antifungal, or antiprotozoal agents are based on amino acid scaffolds. The amino acid skeleton is crucial for their antimicrobial activity, particularly in the case of aminophosphonate or aminoboronate analogs. The synthesis of amino acid antimicrobials presents a specific challenge, especially in terms of enantioselective methods.
Review
Chemistry, Applied
Hao-Qiang Cao, Jun-Kuan Li, Fa-Guang Zhang, Dominique Cahard, Jun-An Ma
Summary: This review comprehensively summarizes modern synthetic methods towards asymmetric construction of chiral amino carboxylic-phosphonic acid derivatives, including phosphono-containing amino acid derivatives and catalytic enantioselective synthesis as a potent strategy. Topics such as chiral resolution protocols, chiral auxiliary-directed syntheses, and valorization of abundant chiral amino acid resources are also discussed.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Biochemical Research Methods
Hayden R. Anderson, Wei L. Reeves, Andrew T. Bockus, Paolo Suating, Amy G. Grice, Madeleine Gallagher, Adam R. Urbach
Summary: We have developed a novel insulin derivative that exhibits high nanomolar affinity for the synthetic receptor cucurbit[7]uril (Q7), potentially enabling the development of continuous insulin detection methods for diabetes management.
BIOCONJUGATE CHEMISTRY
(2023)
Article
Chemistry, Organic
Evan Savelson, Jetze J. Tepe
Summary: This paper describes a highly divergent synthesis of the indole-oxazole scaffold via a one-pot Friedel-Crafts/Robinson-Gabriel synthesis and its successful application to the synthesis of breitfussins C, G, and H.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Aibo Li, Xinjian Song, Qiao Ren, Peiwang Bao, Xinyu Long, Fuli Huang, Lvjiang Yuan, Jianrong Steve Zhou, Xurong Qin
Summary: A cobalt-catalyzed deuteration of amidoacrylates using deuterated methanol resulted in the synthesis of highly enantioselective α,β-dideuterio-α-amino esters with almost complete deuteration (99%). This new protocol was successfully employed for the preparation of dideuterio-α-amino acid fragments in certain drugs, and also applied in the concise synthesis of dideuterio L-DOPA.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jose F. Rodriguez, Anji Zhang, Ramon Arora, Mark Lautens
Summary: A novel method for the synthesis of 1-amino-2,2,2-trifluoroalkylphosphonates was demonstrated by reacting alkene-tethered trifluoroacetimidoyl chlorides with trialkyl phosphites. The reaction proved to be scalable and yielded products in moderate to good amounts. The proposed mechanism involves the formation of an imidoyl phosphonate intermediate, which is susceptible to nucleophilic attack at nitrogen due to electron-withdrawing groups at the imidoyl carbon.
Article
Chemistry, Organic
Jakub Adamek, Paulina Zielezny, Karol Erfurt
Summary: The report describes the development and optimization of a highly efficient and simple one-pot method for the synthesis of N-protected 1-aminoalkylphosphonium salts in the presence of triarylphosphonium salts. Reactions are mild, catalyst-free, and suitable for larger scale experiments in typical laboratories.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Mohammad Z. Abidin, Thangavelu Saravanan, Laura Bothof, Pieter G. Tepper, Andy-Mark W. H. Thunnissen, Gerrit J. Poelarends
Summary: The study presents the asymmetric synthesis of N-arylalkyl-substituted l-aspartic acids using EDDS lyase as a biocatalyst, resulting in products with good enantioselectivity and high yields. This demonstrates that C-N lyases can serve as a powerful synthetic tool for preparing difficult noncanonical amino acids.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Abhilash Rana, Bhanwar Kumar Malviya, Deepak Kumar Jaiswal, P. Srihari, Ajay K. Singh
Summary: This paper presents an approach for chemical synthesis using solar energy, utilizing an integrated programmed solar panel micro-flow platform for Wolff rearrangements to synthesize various compounds. The method does not require a metal catalyst and utilizes sunlight as an energy source, providing a greener and more efficient approach.
Article
Chemistry, Medicinal
Eleni Sflakidou, Panayiotis Dalezis, Dimitrios T. Trafalis, Vasiliki Sarli
Summary: Novel steroidal alkylating agents with POPAM-OH demonstrated significant anticancer efficacy and reduced toxicity in vitro and in vivo, making them promising candidates for cancer therapy.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Zhegao Ye, Ziran Lei, Xiaodong Ye, Liejin Zhou, Yanan Wang, Zheliang Yuan, Feng Gao, Robert Britton
Summary: A mild and general method for trifluoromethylthiolation of aldehydes using N-trifluoromethylthiosaccharin and sodium decatungstate as the photocatalyst has been reported. Electron-rich aldehydes show better reactivity, while good selectivity is observed for the trifluoromethylthiolation of aldehydic C-H bonds. Preliminary mechanistic studies suggest a free radical process is involved.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Rakesh Pahwa, Jatin Chhabra, Raj Kumar, Rakesh Narang
Summary: This paper discusses key approaches to address resistance associated with melphalan, as well as chemical and formulation developments to enhance its characteristics and targeted profile. The rationale of the article also summarizes recent analytical methods, structure-activity relationship, pharmacokinetics, interactions, potential adverse effects, and medicinal updates of melphalan, including synthetic developments, derivatives, conjugates, and prodrugs, along with encouraging insights and research findings.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Fuzhuo Li, Li-Cheng Yang, Jingyang Zhang, Jason S. Chen, Hans Renata
Summary: A highly diastereo- and enantioselective biocatalytic transamination method was developed for the preparation of a broad range of aromatic beta-branched alpha-amino acids. The transformation proceeds through dynamic kinetic resolution unique to the optimal enzyme, showcasing its utility for the synthesis of sp(3)-rich cyclic fragments and total synthesis of jomthonic acid A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Biochemistry & Molecular Biology
Stefan Kubik
Summary: The study on the use of cyclic peptides or pseudopeptides as synthetic receptors began even before the field of supramolecular chemistry was established. Initially, the focus was on the development of synthetic ionophores using macrocycles with repeating subunit sequences to investigate the correlation between structure, conformation, and binding properties. With further research, cyclopeptides and related macrocycles have become an important and structurally diverse receptor family.
Article
Chemistry, Multidisciplinary
Cong Fu, Qi Xiong, Lu Xiao, Ling He, Tian Bai, Zongpeng Zhang, Xiu-Qin Dong, Chun-Jiang Wang
Summary: This article proposes a novel approach to the stereodivergent synthesis of carbocyclic alpha-quaternary amino acid derivatives through sequential dual Cu/Ir-catalyzed asymmetric allylation and ring-closing metathesis. The method exhibits high yields, exclusive regioselectivities, and excellent diastereoselectivities and enantioselectivities. Furthermore, it is capable of synthesizing challenging seven and eight-membered carbocyclic alpha-amino acid derivatives.
CHINESE JOURNAL OF CHEMISTRY
(2022)
