Yatakemycin: total synthesis, DNA alkylation, and biological properties

2008 ◽  
Vol 25 (2) ◽  
pp. 220-226 ◽  
Author(s):  
Mark S. Tichenor ◽  
Dale L. Boger
Keyword(s):  
Total Synthesis ◽  
Biological Properties ◽  
Dna Alkylation

The Total Synthesis and Biological Properties of the Cytotoxic Macrolide FD-891 (Ia) and Its Non-Natural (Z)-C12 Isomer (Ib).

ChemInform ◽  
2007 ◽  
Vol 38 (42) ◽  
Author(s):  
Jorge Garcia-Fortanet ◽  
Juan Murga ◽  
Miguel Carda ◽  
J. Alberto Marco ◽  
Ruth Matesanz ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Biological Properties ◽  
Cytotoxic Macrolide

Enantio- and Diastereoselective Total Synthesis of (+)-Panepophenanthrin, a Ubiquitin-Activating Enzyme Inhibitor, and Biological Properties of Its New Derivatives

2006 ◽  
Vol 1 (6) ◽  
pp. 845-851 ◽  
Author(s):  
Masayoshi Matsuzawa ◽  
Hideaki Kakeya ◽  
Junichiro Yamaguchi ◽  
Mitsuru Shoji ◽  
Rie Onose ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Enzyme Inhibitor ◽  
Biological Properties

Total Synthesis of DHA and DPAn-3 non-enzymatic oxylipins

Synthesis ◽  
2021 ◽  
Author(s):  
alexandre guy ◽  
Jérémy Merad ◽  
Thomas Degrange ◽  
Guillaume Reversat ◽  
Valérie Bultel-Poncé ◽  
...  
Keyword(s):  
Oxidative Stress ◽  
Fatty Acids ◽  
Docosahexaenoic Acid ◽  
Polyunsaturated Fatty Acids ◽  
Total Synthesis ◽  
Biological Properties ◽  
Chemical Structures ◽  
Structural Variety ◽  
Synthetic Strategy

Oxylipins are formed in-vivo from polyunsaturated fatty acids (PUFAs). A large structural variety of compounds is grouped under the term oxylipins, which differ from their formation mechanism (involving enzymes or not), as well as their chemical structures (cyclopentanes, tetrahydrofurans, hydroxylated-PUFA etc.). All structures of oxylipins are of great biological interests. Directly correlated to oxidative stress phenomenon, non-enzymatic oxylipins are used as systemic and/or specific biomarkers in various pathologies and more especially, they were found to have their own biological properties. Produced in-vivo as a non-separable mixture of isomers, total synthesis is a keystone to answer biological questions. In this work, we described the total synthesis of three non-enzymatic oxylipins derived from docosahexaenoic acid (DHA) and docosapentanoic acid (DPAn-3) using a unique and convergent synthetic strategy.

scholarly journals First Synthesis of (−)-Altenuene-D3 Suitable as Internal Standard for Isotope Dilution Mass Spectrometry

Molecules ◽  
2019 ◽  
Vol 24 (24) ◽  
pp. 4563
Author(s):  
Michael A. Sebald ◽  
Julian Gebauer ◽  
Thomas Sommerfeld ◽  
Matthias Koch
Keyword(s):  
Mass Spectrometry ◽  
Antimicrobial Activity ◽  
Stable Isotope ◽  
Total Synthesis ◽  
Isotope Dilution ◽  
Isotope Dilution Mass Spectrometry ◽  
Internal Standard ◽  
Biological Properties ◽  
Mycotoxin Analysis ◽  
Activity Optimization

Metabolites from Alternaria fungi exhibit a variety of biological properties such as phytotoxic, cytotoxic, or antimicrobial activity. Optimization of a literature procedure culminated in an efficient total synthesis of (−)-altenuene as well as a stable isotope-labeled derivative suitable for implementation in a LC-MS/MS method for mycotoxin analysis.

Enantio- and Diastereoselective Total Synthesis of (+)-Panepophenanthrin (I), a Ubiquitin-Activating Enzyme Inhibitor, and Biological Properties of Its New Derivatives.

ChemInform ◽  
2007 ◽  
Vol 38 (16) ◽  
Author(s):  
Masayoshi Matsuzawa ◽  
Hideaki Kakeya ◽  
Junichiro Yamaguchi ◽  
Mitsuru Shoji ◽  
Rie Onose ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Enzyme Inhibitor ◽  
Biological Properties

scholarly journals Ultrapotent vinblastines in which added molecular complexity further disrupts the target tubulin dimer–dimer interface

2016 ◽  
Vol 113 (35) ◽  
pp. 9691-9698 ◽  
Author(s):  
Daniel W. Carney ◽  
John C. Lukesh ◽  
Daniel M. Brody ◽  
Manuela M. Brütsch ◽  
Dale L. Boger
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Biological Properties ◽  
Dimer Interface ◽  
Protein Protein Interaction ◽  
Conformational Constraints ◽  
Biological Target ◽  
Molecular Complexity ◽  
Target Binding

Approaches to improving the biological properties of natural products typically strive to modify their structures to identify the essential pharmacophore, or make functional group changes to improve biological target affinity or functional activity, change physical properties, enhance stability, or introduce conformational constraints. Aside from accessible semisynthetic modifications of existing functional groups, rarely does one consider using chemical synthesis to add molecular complexity to the natural product. In part, this may be attributed to the added challenge intrinsic in the synthesis of an even more complex compound. Herein, we report synthetically derived, structurally more complex vinblastines inaccessible from the natural product itself that are a stunning 100-fold more active (IC50 values, 50–75 pM vs. 7 nM; HCT116), and that are now accessible because of advances in the total synthesis of the natural product. The newly discovered ultrapotent vinblastines, which may look highly unusual upon first inspection, bind tubulin with much higher affinity and likely further disrupt the tubulin head-to-tail α/β dimer–dimer interaction by virtue of the strategic placement of an added conformationally well-defined, rigid, and extended C20′ urea along the adjacent continuing protein–protein interface. In this case, the added molecular complexity was used to markedly enhance target binding and functional biological activity (100-fold), and likely represents a general approach to improving the properties of other natural products targeting a protein–protein interaction.

scholarly journals Perspectives from nearly five decades of total synthesis of natural products and their analogues for biology and medicine

2020 ◽  
Vol 37 (11) ◽  
pp. 1404-1435 ◽  
Author(s):  
K. C. Nicolaou ◽  
Stephan Rigol
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Biological Properties ◽  
Review Article ◽  
Total Syntheses

This review article summarises a series of total syntheses of natural and designed molecules primarily for biology and medicine. Aspects of new synthetic strategies and methods and optimisation of biological properties are emphasised.

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