4.5 Article

A one-pot synthesis of α-L-threofuranosyl nucleoside triphosphates (tNTPs)

Journal

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 26, Issue 14, Pages 3271-3273

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2016.05.057

Keywords

TNA triphosphate; Phosphoramidite; One-pot synthesis; Moisture tolerant; Thermal stability

Funding

  1. DARPA Folded Non-Natural Polymers with Biological Function Fold F(x) Program [N66001-14-2-4054]
  2. National Science Foundation [1615804, 1607111]
  3. Direct For Biological Sciences [1607111] Funding Source: National Science Foundation
  4. Direct For Mathematical & Physical Scien
  5. Division Of Chemistry [1615804] Funding Source: National Science Foundation
  6. Div Of Molecular and Cellular Bioscience [1607111] Funding Source: National Science Foundation

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TNA (alpha-L-threofuranosyl nucleoside) triphosphates of adenosine (tATP), guanosine (tGTP), cytidine (tCTP), and thymidine (tTTP) were synthesized from their corresponding 3'-O-phosphoramidite derivatives using a novel one-pot reaction that is less moisture sensitive than traditional methods. The chemically synthesized tNTPs, despite containing an unnatural 3'-triphosphate moiety, are similar in thermal stability to natural nucleotide triphosphates. (C) 2016 Elsevier Ltd. All rights reserved.

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