Stereochemistry of terpene derivatives. Part 6: Chemoenzymatic synthesis of chiral bicyclo[3.1.0]hexane derivatives with olfactory properties

2010 ◽  
Vol 21 (7) ◽  
pp. 805-809 ◽  
Author(s):  
Renata Kuriata ◽  
Kamila Gajcy ◽  
Ilona Turowska-Tyrk ◽  
Stanisław Lochyński
Keyword(s):  
Chemoenzymatic Synthesis ◽  
Terpene Derivatives

A One-Pot Chemoenzymatic Synthesis of (2S,4R)-4-Methylproline Enables the First Total Synthesis of Antiviral Lipopeptide Cavinafungin B

2018 ◽  
Author(s):  
Christian R. Zwick ◽  
Hans Renata
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Complex Molecule ◽  
Molecular Target ◽  
Chemoenzymatic Synthesis ◽  
General Strategy ◽  
One Pot

We report an efficient ten-step synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (Rink-Boc-ATG-resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner.This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

Utilizing terpene derivatives in the synthesis of annulated terpene-imidazoles with application in the nitroaldol reaction

2008 ◽  
Vol 19 (21) ◽  
pp. 2462-2469 ◽  
Author(s):  
Jiří Kulhánek ◽  
Filip Bureš ◽  
Petr Šimon ◽  
W. Bernd Schweizer
Keyword(s):  
Nitroaldol Reaction ◽  
Terpene Derivatives

scholarly journals New Haloterpenes from the Marine Red Alga Laurencia papillosa: Structure Elucidation and Biological Activity

Marine Drugs ◽  
2021 ◽  
Vol 19 (1) ◽  
pp. 35
Author(s):  
Mohamed Shaaban ◽  
Ghada S. E. Abou-El-Wafa ◽  
Christopher Golz ◽  
Hartmut Laatsch
Keyword(s):  
Biological Activity ◽  
Crude Extract ◽  
Structure Elucidation ◽  
Antimicrobial Activities ◽  
Red Alga ◽  
Spectroscopic Methods ◽  
X Ray Diffraction ◽  
X Ray ◽  
Chemical Structures ◽  
Terpene Derivatives

Analysis of the air-dried marine red alga Laurencia papillosa, collected near Ras-Bakr at the Suez gulf (Red Sea) in Egypt delivered five new halogenated terpene derivatives: aplysiolic acid (1), 7-acetyl-aplysiol (2), aplysiol-7-one (3), 11,14-dihydroaplysia-5,11,14,15-tetrol (5a), and a new maneonene derivative 6, named 5-epi-maneolactone. The chemical structures of these metabolites were characterized employing spectroscopic methods, and the relative and absolute configurations were determined by comparison of experimental and ab initio-calculated NMR, NOE, ECD, and ORD data, and by X-ray diffraction of 2 and 6. The antimicrobial activities of the crude extract and compounds 1–3, 5a and 6 were studied.

scholarly journals Recent Advances in the Chemical Biology of N-Glycans

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1040
Author(s):  
Asuka Shirakawa ◽  
Yoshiyuki Manabe ◽  
Koichi Fukase
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Molecular Basis ◽  
Chemical Biology ◽  
Molecular Level ◽  
Chemoenzymatic Synthesis ◽  
Complex Structures ◽  
Recent Advances ◽  
Protein Functions ◽  
Potential Applications

Asparagine-linked N-glycans on proteins have diverse structures, and their functions vary according to their structures. In recent years, it has become possible to obtain high quantities of N-glycans via isolation and chemical/enzymatic/chemoenzymatic synthesis. This has allowed for progress in the elucidation of N-glycan functions at the molecular level. Interaction analyses with lectins by glycan arrays or nuclear magnetic resonance (NMR) using various N-glycans have revealed the molecular basis for the recognition of complex structures of N-glycans. Preparation of proteins modified with homogeneous N-glycans revealed the influence of N-glycan modifications on protein functions. Furthermore, N-glycans have potential applications in drug development. This review discusses recent advances in the chemical biology of N-glycans.

scholarly journals Multidisciplinary Studies of Folk Medicine “Five Thieves’ Oil” (Olejek Pięciu Złodziei) Components

Molecules ◽  
2021 ◽  
Vol 26 (10) ◽  
pp. 2931
Author(s):  
Przemysław Siejak ◽  
Wojciech Smułek ◽  
Farahnaz Fathordobady ◽  
Anna Grygier ◽  
Hanna Maria Baranowska ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Membrane Permeability ◽  
Significant Contribution ◽  
Spectroscopic Analysis ◽  
Folk Medicine ◽  
Cell Activity ◽  
Biological Properties ◽  
Cell Membrane Permeability ◽  
Comparable Activity ◽  
Terpene Derivatives

To meet the growing interest in natural antibacterial agents, we evaluated the physicochemical and biological properties of the folk medicine known as “five thieves’ oil” (Polish name: olejek pięciu złodziei). Five thieves’ oil consists of a mixture of five oils: rosemary, lemon, clove, eucalyptus, and cinnamon. In this study, we performed gas chromatography, FTIR, and UV–vis spectroscopic analysis, as well as L-a-b color tests, contact angle determination, and surface tension determination. To verify its antibacterial activity, the metabolic activity and changes in cell membrane permeability of bacteria of the genus Pseudomonas were studied. As a result, it was found that among the constituent oils, the oils of clove and cinnamon were the least volatile and, at the same time, had the strongest antibacterial activity. However, a mix of all the oils also showed comparable activity, which was even more pronounced for the oils after 4 weeks of aging. This effect can be linked to the high content of terpene derivatives such as eugenol and cinnamaldehyde, which can cause changes in bacterial membrane permeability, affecting cell activity and survival. This study is the first to characterize the constituents of the popular folk medicine five thieves’ oil, confirming and explaining its strong antibacterial activity, thus constituting a significant contribution to contemporary health education.

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