A stereolibrary of conformationally restricted amino acids based on pyrrolidinyl/piperidinyloxazole motifs

2015 ◽  
Vol 21 (6) ◽  
pp. 391-395 ◽  
Author(s):  
Oleksiy S. Artamonov ◽  
Taras Bulda ◽  
Tkhe Kyong Fam ◽  
Evgeniy Y. Slobodyanyuk ◽  
Dmitry M. Volochnyuk ◽  
...  
Keyword(s):  
Amino Acids ◽  
Natural Products ◽  
Drug Discovery ◽  
Carboxylic Acids ◽  
Building Blocks ◽  
Conformationally Restricted ◽  
Lead Compounds ◽  
Restricted Amino Acids

AbstractA stereolibrary of conformationally restricted oxazole-containing amino acids, namely all isomers of 5–pyrrolydinyl- and 5-piperidinyloxazole-4-carboxylic acids, were designed and synthesized in three steps by the reaction of the corresponding N-Boc-protected amino acids and ethyl isocyanoacetate. These natural products-inspired amino acids are valuable building blocks for the synthesis of peptidomimetics and potential lead compounds for drug discovery.

scholarly journals Stereocontrolled Synthesis of Cyclopropanol Amino Acids from Allylic Sulfones: Conformationally Restricted Building Blocks.

ChemInform ◽  
2004 ◽  
Vol 35 (5) ◽  
Author(s):  
David Diez ◽  
P. Garcia ◽  
Isidro S. Marcos ◽  
N. M. Garrido ◽  
P. Basabe ◽  
...  
Keyword(s):  
Amino Acids ◽  
Building Blocks ◽  
Conformationally Restricted ◽  
Stereocontrolled Synthesis

Glycosylated α-Azido Amino Acids: Versatile Intermediates in the Synthesis of Neoglycoconjugates

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 904-907 ◽  
Author(s):  
Trinidad Velasco-Torrijos ◽  
Róisín O’Flaherty
Keyword(s):  
Amino Acids ◽  
Drug Discovery ◽  
Building Blocks ◽  
Sensor Development ◽  
Galactosyl Ceramide

A series of glycosylated α-azido amino acids was synthesized as precursors for neoglycoconjugates, a class of important biomolecules for drug discovery, and sensor development. The synthetically challenging 1,2-cis α-galactosylated species described herein were designed as building blocks in the synthesis of analogues of α-galactosyl ceramide, a potent immunomodulator. A benzyl-protected 1,2,3-triazolyl α-galactosyl-l-serine derivative was prepared using copper azide alkyne cycloaddition to showcase the potential of glycosylated α-azido amino acids in neoglycoconjugate design.

scholarly journals Protein Segments with Conformationally Restricted Amino Acids Can Control Supramolecular Organization at the Nanoscale

2009 ◽  
Vol 49 (7) ◽  
pp. 1623-1629 ◽  
Author(s):  
David Zanuy ◽  
Gema Ballano ◽  
Ana I. Jiménez ◽  
Jordi Casanovas ◽  
Nurit Haspel ◽  
...  
Keyword(s):  
Amino Acids ◽  
Supramolecular Organization ◽  
Conformationally Restricted ◽  
Restricted Amino Acids

scholarly journals Synthesis of Bifunctional Molecules for the Production of Polymers Based on Unsaturated Fatty Acids as Bioderived Raw Materials

2020 ◽  
Vol 1 (3) ◽  
pp. 275-289
Author(s):  
Alessa Hinzmann ◽  
Selina Sophie Druhmann ◽  
Harald Gröger
Keyword(s):  
Amino Acids ◽  
Fatty Acids ◽  
Carboxylic Acids ◽  
Unsaturated Fatty Acids ◽  
Raw Materials ◽  
Building Blocks ◽  
Product Formation ◽  
Bifunctional Molecules ◽  
Biorenewable Resources ◽  
Aldoxime Dehydratase

Currently, investigations of polymer-building blocks made from biorenewable feedstocks such as, for example, fatty acids, are of high interest for the chemical industry. An alternative synthesis of nitrile-substituted aliphatic carboxylic acids as precursors for ω-amino acids, which are useful to produce polymers, was investigated starting from biorenewable fatty acids. By hydroformylation of unsaturated fatty acids or unsaturated acids being accessible from unsaturated fatty acids by cross-metathesis reactions, aldehydes are formed. In this work, the hydroformylation of such unsaturated acids led to the formation of the corresponding aldehydes, which were afterwards converted with hydroxylamine to aldoximes. Subsequent dehydration by an aldoxime dehydratase as a biocatalyst or by CuII acetate led to the desired nitriles. Within this work, C7-, C9- and C11-carboxylic acids with a terminal nitrile functionality as well as a branched nitrile-functionalized stearate derivative were synthesized by means of this approach. As these nitriles serve as precursors for amino acids being suitable for polymerization, this work represents an alternative synthetic access to polyamide precursors, which starts directly from unsaturated fatty acids as biorenewable resources and avoids harsh reaction conditions as well as and by-product formation.

scholarly journals Natural products as lead compounds in drug discovery

2013 ◽  
Vol 15 (7) ◽  
pp. 764-788 ◽  
Author(s):  
Jabeena Khazir ◽  
Bilal Ahmad Mir ◽  
Shabir Ahmad Mir ◽  
Don Cowan
Keyword(s):  
Natural Products ◽  
Drug Discovery ◽  
Lead Compounds

Stereocontrolled Synthesis of Cyclopropanol Amino Acids from Allylic Sulfones:  Conformationally Restricted Building Blocks

2003 ◽  
Vol 5 (20) ◽  
pp. 3687-3690 ◽  
Author(s):  
David Díez ◽  
P. Garcia ◽  
Isidro S. Marcos ◽  
N. M. Garrido ◽  
P. Basabe ◽  
...  
Keyword(s):  
Amino Acids ◽  
Building Blocks ◽  
Conformationally Restricted ◽  
Stereocontrolled Synthesis

scholarly journals Natural Products as Potential Lead Compounds for Drug Discovery Against SARS-CoV-2

2021 ◽  
Author(s):  
Oyere Tanyi Ebob ◽  
Smith B. Babiaka ◽  
Fidele Ntie-Kang
Keyword(s):  
Natural Products ◽  
Drug Discovery ◽  
Infectious Diseases ◽  
Review Article ◽  
Literature Survey ◽  
Lead Compounds ◽  
The Past ◽  
The World ◽  
Bacteria And Fungi ◽  
New Vaccines

AbstractFor the past 2 years, the coronavirus responsible for the COVID-19 infection has become a world pandemic, ruining the lives and economies of several nations in the world. This has scaled up research on the virus and the resulting infection with the goal of developing new vaccines and therapies. Natural products are known to be a rich source of lead compounds for drug discovery, including against infectious diseases caused by microbes (viruses, bacteria and fungi). In this review article, we conducted a literature survey aimed at identifying natural products with inhibitory concentrations against the coronaviruses or their target proteins, which lie below 10 µM. This led to the identification of 42 compounds belonging to the alkaloid, flavonoid, terpenoid, phenolic, xanthone and saponin classes. The cut off concentration of 10 µM was to limit the study to the most potent chemical entities, which could be developed into therapies against the viral infection to make a contribution towards limiting the spread of the disease.

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