Synthesis, Properties, Biological Activity, and Medicinal Chemistry of Marine Nucleosides

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (30 April 2019) | Viewed by 5486

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Guest Editor
Department of Chemistry, University of Colorado Denver, Denver, CO, USA
Interests: structure–function relationships of chemically modified RNA; 8-oxoG and 8-oxopurines within RNA; ribonucleolytic activity of oxidized RNA; chemical synthesis of modified RNA and DNA
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Special Issue Information

Dear Colleagues,

Nucleosides are an intrinsic part of all organisms and are involved in key processes that maintain life. Therefore, their presence within marine species is not surprising and is, and has been, an area of interest. The fact that nucleoside derivatives have been approved for certain treatments provide evidence of the potential that derivatives containing nucleosides as backbone have in the biomedical field. Examples highlighting the relationship between purine/pyrimidine derivatives, the backbone of nucleobases in DNA and RNA, and marine resources include their isolation from various sources in the marine world and have been studied in different contexts, e.g., as synthons for drug derivatives, as drug leads, within natural product biodiversity, determination of bioactivity, or basic research.

The aim of this Special Issue is to deliver a forum that expands interest on this topic to researchers in various fields, and highlights the potential of marine nucleosides as a central piece with interdisciplinary applications. This issue will provide up to date reports around developments, applications, or any topic regarding marine nucleosides broadly, and their role in fields spanning from biology and biochemistry to organic and physical organic chemistry. This includes, but is not limited to, aspects of natural products containing nucleosides, i.e., their biosynthesis, isolation, characterization, or use as potential drug derivatives; total synthesis as well as synthetic efforts towards novel derivatives containing nucleosides; effectivity of drug-containing nucleosides; biophysical and photophysical properties; proposed biosynthetic pathways; overall biochemical properties; or effects on living systems. Review articles pertaining to this field are also welcomed.

Dr. Marino Resendiz
Guest Editor

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Keywords

  • Natural product synthesis/isolation/characterization/biosynthesis
  • biological activity of products derived from marine nucleosides
  • marine nucleosides as backbone of derivatives with interesting properties
  • chemical/photochemical/biological reactivity of marine nucleosides and their derivatives

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Published Papers (1 paper)

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Research

11 pages, 1242 KiB  
Communication
Total Synthesis of Mycalisine B
by Haixin Ding, Zhizhong Ruan, Peihao Kou, Xiangyou Dong, Jiang Bai and Qiang Xiao
Mar. Drugs 2019, 17(4), 226; https://doi.org/10.3390/md17040226 - 14 Apr 2019
Cited by 8 | Viewed by 5008
Abstract
The first total synthesis of the marine nucleoside Mycalisine B—a naturally occurring and structurally distinct 4,5-unsaturated 7-deazapurine nucleoside—has been accomplished in 10 linear steps with 27.5% overall yield from commercially available 1,2,3,5-tetra-O-acetyl-ribose and tetracyanoethylene. Key steps of the approach include: (1) [...] Read more.
The first total synthesis of the marine nucleoside Mycalisine B—a naturally occurring and structurally distinct 4,5-unsaturated 7-deazapurine nucleoside—has been accomplished in 10 linear steps with 27.5% overall yield from commercially available 1,2,3,5-tetra-O-acetyl-ribose and tetracyanoethylene. Key steps of the approach include: (1) I2 catalyzed acetonide formation from 1,2,3,5-tetra-O-acetylribose and acetone at large scale; (2) Vorbrüggen glycosylation using N4-benzoyl-5-cyano-6-bromo-7H-pyrrolo[2,3–d]pyrimidine as a nucleobase to avoid formation of N-3 isomer; (3) mild and scalable reaction conditions. Full article
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